SK277996B6 - Method of production of 8-alpha-acylaminoergolines - Google Patents

Method of production of 8-alpha-acylaminoergolines Download PDF

Info

Publication number: SK277996B6
Authority: SK; Slovakia
Prior art keywords: alkyl; exp; sub; acid; formula
Prior art date: 1989-05-12

Application number

SK2604-91A

Other languages

English (en)

Slovak (sk)

Other versions

SK260491A3 (en

Inventor

Gerhard Sauer

Thomas Brumby

Helmut Wachtel

Jonathan Turner

Peter-Andreas Loschmann

Original Assignee

Gerhard Sauer

Thomas Brumby

Helmut Wachtel

Jonathan Turner

Peter-Andreas Loschmann

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.)

1989-05-12

Filing date

1990-05-11

Publication date

1995-09-13

1990-05-11 Application filed by Gerhard Sauer, Thomas Brumby, Helmut Wachtel, Jonathan Turner, Peter-Andreas Loschmann filed Critical Gerhard Sauer

1995-09-13 Publication of SK260491A3 publication Critical patent/SK260491A3/sk

1995-09-13 Publication of SK277996B6 publication Critical patent/SK277996B6/sk

Links

238000000034 method Methods 0.000 title claims description 6
150000001875 compounds Chemical class 0.000 claims abstract description 15
239000002253 acid Substances 0.000 claims abstract description 13
150000003839 salts Chemical class 0.000 claims abstract description 11
239000012038 nucleophile Substances 0.000 claims abstract description 5
238000002360 preparation method Methods 0.000 claims description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
239000000654 additive Substances 0.000 abstract 2
230000000996 additive effect Effects 0.000 abstract 2
150000007513 acids Chemical class 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
-1 1-methyl-1-ethylpropyl Chemical group 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 5
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 4
239000000203 mixture Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000003042 antagnostic effect Effects 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
125000001316 cycloalkyl alkyl group Chemical group 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
229960003638 dopamine Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
150000002430 hydrocarbons Chemical group 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
230000028327 secretion Effects 0.000 description 2
239000000243 solution Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
150000003585 thioureas Chemical class 0.000 description 2
125000006021 1-methyl-2-propenyl group Chemical group 0.000 description 1
125000006017 1-propenyl group Chemical group 0.000 description 1
PMCHWEAOALOWHE-QTGUNEKASA-N 3-[(6aR,9S,10aR)-5-methyl-7-propyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinolin-9-yl]-1-[2-(dimethylamino)ethyl]-1-ethylthiourea Chemical compound C(C)N(C(=S)N[C@@H]1CN([C@@H]2CC3=C(NC4=CC=CC([C@H]2C1)=C34)C)CCC)CCN(C)C PMCHWEAOALOWHE-QTGUNEKASA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
102000009151 Luteinizing Hormone Human genes 0.000 description 1
108010073521 Luteinizing Hormone Proteins 0.000 description 1
RGKPVRBYOYGLRL-UCNVEGJOSA-N O-[3-(dimethylamino)propyl] N-[(6aR,9S,10aR)-5-methyl-7-propyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinolin-9-yl]carbamothioate Chemical compound CN(CCCOC(N[C@@H]1CN([C@@H]2CC3=C(NC4=CC=CC([C@H]2C1)=C34)C)CCC)=S)C RGKPVRBYOYGLRL-UCNVEGJOSA-N 0.000 description 1
208000018737 Parkinson disease Diseases 0.000 description 1
102000003946 Prolactin Human genes 0.000 description 1
108010057464 Prolactin Proteins 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000000872 buffer Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001735 carboxylic acids Chemical group 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
230000003291 dopaminomimetic effect Effects 0.000 description 1
239000008298 dragée Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002168 ethanoic acid esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 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
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229940040129 luteinizing hormone Drugs 0.000 description 1
235000019359 magnesium stearate Nutrition 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
230000002503 metabolic effect Effects 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000001282 organosilanes Chemical class 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
229940097325 prolactin Drugs 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000011924 stereoselective hydrogenation Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
ZHZOIVSXSKARMO-UHFFFAOYSA-N tert-butyl chlorate Chemical compound CC(C)(C)OCl(=O)=O ZHZOIVSXSKARMO-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003556 thioamides Chemical class 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
238000009736 wetting 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

SK2604-91A 1989-05-12 1990-05-11 Method of production of 8-alpha-acylaminoergolines SK277996B6 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3915950A DE3915950A1 (de)	1989-05-12	1989-05-12	8(alpha)-acylamino-ergoline, ihre herstellung und verwendung als arzneimittel

Publications (2)

Publication Number	Publication Date
SK260491A3 SK260491A3 (en)	1995-09-13
SK277996B6 true SK277996B6 (en)	1995-09-13

Family

ID=6380759

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
SK2604-91A SK277996B6 (en)	1989-05-12	1990-05-11	Method of production of 8-alpha-acylaminoergolines
SK2331-90A SK277997B6 (en)	1989-05-12	1990-05-11	8alpha-acylaminoergolines, method of their production and using as medicaments

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
SK2331-90A SK277997B6 (en)	1989-05-12	1990-05-11	8alpha-acylaminoergolines, method of their production and using as medicaments

Country Status (14)

Country	Link
US (2)	US5212178A (cs)
EP (1)	EP0427827B1 (cs)
JP (1)	JPH04500681A (cs)
AT (1)	ATE147742T1 (cs)
CA (1)	CA2028832A1 (cs)
CZ (2)	CZ279080B6 (cs)
DD (1)	DD294259A5 (cs)
DE (2)	DE3915950A1 (cs)
DK (1)	DK0427827T3 (cs)
ES (1)	ES2098263T3 (cs)
HU (1)	HU212814B (cs)
PT (1)	PT94011B (cs)
SK (2)	SK277996B6 (cs)
WO (1)	WO1990013550A1 (cs)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6018332A (en) *	1997-11-21	2000-01-25	Ark Interface Ii, Inc.	Overscan user interface
US8113807B2 (en) *	2007-08-24	2012-02-14	Timothy Wilkinson	Methods and apparatus for fabricating structures
SG10201509139QA (en) *	2011-12-19	2015-12-30	Map Pharmaceuticals Inc	Novel iso-ergoline derivatives
MX2017009405A (es)	2015-01-20	2018-01-18	Xoc Pharmaceuticals Inc	Compuestos de tipo ergolina y usos de estos.
EP3247357A4 (en)	2015-01-20	2018-07-11	Xoc Pharmaceuticals, Inc	Isoergoline compounds and uses thereof
WO2018223065A1 (en)	2017-06-01	2018-12-06	Xoc Pharmaceuticals, Inc.	Ergoline derivatives for use in medicine

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2864822A (en) *	1956-10-22	1958-12-16	Lilly Co Eli	9-amino-7-methyl-belta10-ergolene and derivatives thereof
CH615929A5 (en) *	1975-06-02	1980-02-29	Sandoz Ag	Process for the preparation of novel ergoline compounds
WO1982000463A1 (en) *	1980-07-25	1982-02-18	Ag Sandoz	Ergoline derivatives,method for their preparation,pharmaceutical compositions containing them and their therapeutic application
DE3135305C2 (de) *	1981-09-03	1983-07-21	Schering Ag, 1000 Berlin Und 4619 Bergkamen	Verfahren zur Herstellung von 8-Ergolinyl-harnstoffen
DE3151912A1 (de) *	1981-12-23	1983-06-30	Schering Ag, 1000 Berlin Und 4619 Bergkamen	Neue ergolin-aminoderivate, verfahren zu ihrer herstellung und deren verwendung als arzneimittel
NL8400333A (nl) *	1983-02-16	1984-09-17	Sandoz Ag	Moederkoornalkaloiden, hun bereiding en hun toepassing.
DE3309493A1 (de) *	1983-03-14	1984-09-20	Schering AG, 1000 Berlin und 4709 Bergkamen	Neue ergolin-derivate, verfahren zu ihrer herstellung sowie verwendung als arzneimittel
HU197569B (en) *	1984-01-12	1989-04-28	Sandoz Ag	Process for producing 8alpha-acylaminoergoline derivatives and pharmaceuticals comprising such compounds
DE3587860D1 (de) *	1984-04-09	1994-07-28	Schering Ag	2-substituierte Ergolin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel.
DE3544365A1 (de) *	1984-12-24	1986-07-03	Sandoz-Patent-GmbH, 7850 Lörrach	8(alpha)-acylaminoergoline
HU195810B (en) *	1984-12-24	1988-07-28	Sandoz Ag	Process for preparing new 8alpha-acyl-amino-ergoline derivatives and pharmaceutical compositions containing such compounds
DE3528584A1 (de) *	1985-08-06	1987-02-19	Schering Ag	Neue 1-alkyl-ergolin-thioharnstoffderivate
DE3700825A1 (de) *	1986-01-24	1987-07-30	Sandoz Ag	8(alpha)-acylaminoergoline, ihre herstellung und verwendung
NL8700046A (nl) *	1986-01-24	1987-08-17	Sandoz Ag	8 alfa-acylaminoergolinen, werkwijzen voor hun bereiding en farmaceutische preparaten die ze bevatten.
DE3620293A1 (de) *	1986-06-16	1987-12-17	Schering Ag	1-und/oder 2-substituierte ergolinderivate
DE3708028A1 (de) *	1987-03-10	1988-09-22	Schering Ag	Verfahren zur herstellung von 2,3ss-dihydroergolinen, 2-substituierte 2,3ss-dihydroergoline und ihre verwendung als arzneimittel

1989
- 1989-05-12 DE DE3915950A patent/DE3915950A1/de not_active Ceased
1990
- 1990-05-10 ES ES90906872T patent/ES2098263T3/es not_active Expired - Lifetime
- 1990-05-10 HU HU904426A patent/HU212814B/hu not_active IP Right Cessation
- 1990-05-10 JP JP2506904A patent/JPH04500681A/ja active Pending
- 1990-05-10 CA CA002028832A patent/CA2028832A1/en not_active Abandoned
- 1990-05-10 AT AT90906872T patent/ATE147742T1/de not_active IP Right Cessation
- 1990-05-10 DE DE59010633T patent/DE59010633D1/de not_active Expired - Lifetime
- 1990-05-10 DK DK90906872.8T patent/DK0427827T3/da active
- 1990-05-10 WO PCT/DE1990/000339 patent/WO1990013550A1/de not_active Ceased
- 1990-05-10 EP EP90906872A patent/EP0427827B1/de not_active Expired - Lifetime
- 1990-05-11 SK SK2604-91A patent/SK277996B6/sk unknown
- 1990-05-11 CZ CS912604A patent/CZ279080B6/cs unknown
- 1990-05-11 DD DD90340575A patent/DD294259A5/de not_active IP Right Cessation
- 1990-05-11 SK SK2331-90A patent/SK277997B6/sk unknown
- 1990-05-11 CZ CS902331A patent/CZ278981B6/cs unknown
- 1990-05-11 PT PT94011A patent/PT94011B/pt not_active IP Right Cessation
- 1990-05-14 US US07/522,751 patent/US5212178A/en not_active Expired - Fee Related
1994
- 1994-12-27 US US08/364,015 patent/US5547958A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
ATE147742T1 (de)	1997-02-15
DE3915950A1 (de)	1990-11-15
WO1990013550A1 (de)	1990-11-15
EP0427827A1 (de)	1991-05-22
DD294259A5 (de)	1991-09-26
US5212178A (en)	1993-05-18
CZ260491A3 (en)	1993-03-17
HUT56363A (en)	1991-08-28
CZ279080B6 (en)	1994-12-15
SK260491A3 (en)	1995-09-13
DE59010633D1 (de)	1997-03-06
CZ233190A3 (en)	1994-02-16
CA2028832A1 (en)	1990-11-13
SK233190A3 (en)	1995-09-13
EP0427827B1 (de)	1997-01-15
HU212814B (hu)	1998-08-28
HU904426D0 (en)	1991-07-29
JPH04500681A (ja)	1992-02-06
US5547958A (en)	1996-08-20
PT94011B (pt)	1996-12-31
DK0427827T3 (da)	1997-07-07
CZ278981B6 (en)	1994-11-16
SK277997B6 (en)	1995-09-13
ES2098263T3 (es)	1997-05-01
PT94011A (pt)	1991-01-08

Publication	Publication Date	Title
FI86064C (fi)	1992-07-10	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara aminotiazol- och aminooxazolderivat.
EP0126968B1 (en)	1988-12-21	Ergoline derivatives, processes for their preparation and pharmaceutical compositions containing same
HU201955B (en)	1991-01-28	Process for producing new ribofuranuronic acid derivatives and pharmaceutical compositions comprising such compounds
SK277996B6 (en)	1995-09-13	Method of production of 8-alpha-acylaminoergolines
EP0289746B1 (en)	1994-10-19	1,4-Dihydropyridine derivatives and pharmaceutical composition thereof
US5401748A (en)	1995-03-28	2,14-disubstituted ergolines, their production and use in pharmaceutical compositions
US4260610A (en)	1981-04-07	Disubstituted piperazines
IE862485L (en)	1987-03-19	Bromoergoline derivatives
US4176182A (en)	1979-11-27	Sulfamoyl derivatives of 8-β-aminomethylergoline
CA1293247C (en)	1991-12-17	Ergoline derivatives
EP0254527B1 (en)	1993-01-27	Tetracyclic indole derivatives
SE435511B (sv)	1984-10-01	Analogiforfarande for framstellning av oktahydro-indolo(2,3-a)kinoliziner
GB2125041A (en)	1984-02-29	Ergot alkaloids
JPS63222170A (ja)	1988-09-16	エルゴリニルヘテロサイクル類
FI83869B (fi)	1991-05-31	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara ergolinderivat.
US4782063A (en)	1988-11-01	Ergoline esters useful as serotonin antagonists
CS245790B2 (cs)	1986-10-16	Způsob výroby derivátů ergolinu
PL131550B1 (en)	1984-11-30	Method of obtaining compounds having nitrogen atom at nodal position
SK277964B6 (en)	1995-09-13	Method of production of 2-substituted ergolines
CS245799B2 (cs)	1986-10-16	Způsob výroby derivátů ergolinu