LU87047A1 - Nouveaux derives de l'octahydrobenzo(g)quinoleene,leur preparation et leur utilisation comme medicaments - Google Patents

Nouveaux derives de l'octahydrobenzo(g)quinoleene,leur preparation et leur utilisation comme medicaments

Info

Publication number: LU87047A1
Authority: LU; Luxembourg
Prior art keywords: formula; compound; signify; hydrogen; group
Prior art date: 1986-11-21

Application number

LU87047A

Other languages

English (en)

French (fr)

Original Assignee

Sandoz Sa

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.)

1986-11-21

Filing date

1987-11-18

Publication date

1988-06-13

1987-11-18 Application filed by Sandoz Sa filed Critical Sandoz Sa

1988-06-13 Publication of LU87047A1 publication Critical patent/LU87047A1/fr

Links

238000002360 preparation method Methods 0.000 title claims description 9
239000003814 drug Substances 0.000 title claims description 8
150000001875 compounds Chemical class 0.000 claims description 56
239000002253 acid Substances 0.000 claims description 27
239000001257 hydrogen Substances 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 17
239000012458 free base Substances 0.000 claims description 15
238000000034 method Methods 0.000 claims description 14
239000000203 mixture Substances 0.000 claims description 12
150000002431 hydrogen Chemical class 0.000 claims description 10
102000003946 Prolactin Human genes 0.000 claims description 9
108010057464 Prolactin Proteins 0.000 claims description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
229940097325 prolactin Drugs 0.000 claims description 9
-1 hydroxy, methoxy Chemical group 0.000 claims description 8
230000003287 optical effect Effects 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
230000028327 secretion Effects 0.000 claims description 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
239000004202 carbamide Substances 0.000 claims description 5
125000004423 acyloxy group Chemical group 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 4
230000003291 dopaminomimetic effect Effects 0.000 claims description 4
230000002401 inhibitory effect Effects 0.000 claims description 4
239000013543 active substance Substances 0.000 claims description 3
125000001033 ether group Chemical group 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
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 3
125000004846 (C1-C4) allyl group Chemical group 0.000 claims description 2
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
239000005711 Benzoic acid Substances 0.000 claims description 2
235000010233 benzoic acid Nutrition 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
230000004936 stimulating effect Effects 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
QJMIKHWBGQHYPT-UHFFFAOYSA-N 1,2,3,4,4a,5,5a,6-octahydrobenzo[g]quinoline Chemical class C1=CCC2CC(CCCN3)C3=CC2=C1 QJMIKHWBGQHYPT-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
150000001718 carbodiimides Chemical class 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000006260 foam Substances 0.000 description 2
125000004356 hydroxy functional group Chemical group O* 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
239000000155 melt Substances 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
230000007017 scission Effects 0.000 description 2
235000017550 sodium carbonate Nutrition 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 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
241001633635 Ademon Species 0.000 description 1
201000000736 Amenorrhea Diseases 0.000 description 1
206010001928 Amenorrhoea Diseases 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
208000001287 Galactorrhea Diseases 0.000 description 1
206010017600 Galactorrhoea Diseases 0.000 description 1
206010058359 Hypogonadism Diseases 0.000 description 1
240000006240 Linum usitatissimum Species 0.000 description 1
208000019255 Menstrual disease Diseases 0.000 description 1
150000007945 N-acyl ureas Chemical class 0.000 description 1
208000018737 Parkinson disease Diseases 0.000 description 1
229940123796 Prolactin inhibitor Drugs 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
231100000540 amenorrhea Toxicity 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
238000013475 authorization Methods 0.000 description 1
239000002585 base Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
229960002802 bromocriptine Drugs 0.000 description 1
OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000003136 dopamine receptor stimulating agent Substances 0.000 description 1
229940005501 dopaminergic agent Drugs 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000006651 lactation Effects 0.000 description 1
230000002045 lasting effect Effects 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
125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010956 selective crystallization Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
230000001225 therapeutic effect Effects 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
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/08—Aza-anthracenes
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

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

LU87047A 1986-11-21 1987-11-18 Nouveaux derives de l'octahydrobenzo(g)quinoleene,leur preparation et leur utilisation comme medicaments LU87047A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE3639855		1986-11-21
DE3639855		1986-11-21

Publications (1)

Publication Number	Publication Date
LU87047A1 true LU87047A1 (fr)	1988-06-13

Family

ID=6314490

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU87047A LU87047A1 (fr)	1986-11-21	1987-11-18	Nouveaux derives de l'octahydrobenzo(g)quinoleene,leur preparation et leur utilisation comme medicaments

Country Status (22)

Country	Link
JP (1)	JPS63150264A (de)
KR (1)	KR880006200A (de)
AT (1)	AT393836B (de)
AU (1)	AU604512B2 (de)
BE (1)	BE1003219A3 (de)
CH (1)	CH677668A5 (de)
DK (1)	DK608787A (de)
ES (1)	ES2011309A6 (de)
FI (1)	FI875130A7 (de)
FR (1)	FR2607134A1 (de)
GB (1)	GB2198129B (de)
GR (1)	GR871777B (de)
HU (1)	HUT47914A (de)
IL (1)	IL84538A (de)
IT (1)	IT1211920B (de)
LU (1)	LU87047A1 (de)
NL (1)	NL8702680A (de)
NZ (1)	NZ222612A (de)
PH (1)	PH25125A (de)
PT (1)	PT86178B (de)
SE (1)	SE8704551L (de)
ZA (1)	ZA878717B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU3879789A (en) *	1988-07-22	1990-02-19	Sandoz Ag	Use of benzo(g)quinolines in treatment of nicotine addiction
TW357143B (en) *	1995-07-07	1999-05-01	Novartis Ag	Benzo[g]quinoline derivatives

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4526892A (en) *	1981-03-03	1985-07-02	Farmitalia Carlo Erba, S.P.A.	Dimethylaminoalkyl-3-(ergoline-8'βcarbonyl)-ureas
DE3280252D1 (de) *	1981-10-16	1990-10-31	Sandoz Ag	1,2,3,4,4a,5,10,10a-octahydrobenzo(g)chinolin-derivate mit pharmazeutischer wirkung.
GB8602372D0 (en) *	1986-01-31	1986-03-05	Sandoz Ltd	Organic compounds

1987
- 1987-11-10 NL NL8702680A patent/NL8702680A/nl not_active Application Discontinuation
- 1987-11-12 CH CH4410/87A patent/CH677668A5/de not_active IP Right Cessation
- 1987-11-13 HU HU875063A patent/HUT47914A/hu unknown
- 1987-11-16 FR FR8715917A patent/FR2607134A1/fr not_active Withdrawn
- 1987-11-16 BE BE8701295A patent/BE1003219A3/fr not_active IP Right Cessation
- 1987-11-18 IT IT8748620A patent/IT1211920B/it active
- 1987-11-18 LU LU87047A patent/LU87047A1/fr unknown
- 1987-11-19 IL IL84538A patent/IL84538A/xx unknown
- 1987-11-19 AU AU81409/87A patent/AU604512B2/en not_active Ceased
- 1987-11-19 FI FI875130A patent/FI875130A7/fi not_active IP Right Cessation
- 1987-11-19 NZ NZ222612A patent/NZ222612A/xx unknown
- 1987-11-19 SE SE8704551A patent/SE8704551L/xx not_active Application Discontinuation
- 1987-11-19 PT PT86178A patent/PT86178B/pt not_active IP Right Cessation
- 1987-11-19 DK DK608787A patent/DK608787A/da not_active Application Discontinuation
- 1987-11-19 GB GB8727057A patent/GB2198129B/en not_active Expired - Lifetime
- 1987-11-20 ES ES8703316A patent/ES2011309A6/es not_active Expired - Lifetime
- 1987-11-20 KR KR870013071A patent/KR880006200A/ko not_active Withdrawn
- 1987-11-20 AT AT0306187A patent/AT393836B/de not_active IP Right Cessation
- 1987-11-20 GR GR871777A patent/GR871777B/el unknown
- 1987-11-20 PH PH36098A patent/PH25125A/en unknown
- 1987-11-20 JP JP62294995A patent/JPS63150264A/ja active Pending
- 1987-11-20 ZA ZA878717A patent/ZA878717B/xx unknown

Also Published As

Publication number	Publication date
ATA306187A (de)	1991-06-15
DK608787D0 (da)	1987-11-19
GB2198129A (en)	1988-06-08
IT8748620A0 (it)	1987-11-18
AT393836B (de)	1991-12-27
NZ222612A (en)	1991-07-26
ES2011309A6 (es)	1990-01-01
GB2198129B (en)	1990-08-08
PT86178B (pt)	1990-11-07
ZA878717B (en)	1989-06-28
NL8702680A (nl)	1988-06-16
JPS63150264A (ja)	1988-06-22
DK608787A (da)	1988-05-22
SE8704551L (sv)	1988-05-22
KR880006200A (ko)	1988-07-22
FI875130A0 (fi)	1987-11-19
SE8704551D0 (sv)	1987-11-19
AU604512B2 (en)	1990-12-20
AU8140987A (en)	1988-05-26
CH677668A5 (de)	1991-06-14
IL84538A0 (en)	1988-04-29
IT1211920B (it)	1989-11-08
BE1003219A3 (fr)	1992-02-04
GR871777B (en)	1988-03-24
GB8727057D0 (en)	1987-12-23
PH25125A (en)	1991-02-19
HUT47914A (en)	1989-04-28
IL84538A (en)	1991-12-12
PT86178A (en)	1987-12-01
FI875130A7 (fi)	1988-05-22
FR2607134A1 (fr)	1988-05-27

Publication	Publication Date	Title
EP0302788B1 (de)	1992-02-05	2-[Methyl(4-piperidinyl)]-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indolderivate, ihre Herstellung und therapeutische Verwendung
EP0636608A1 (de)	1995-02-01	Derivate von 1-Benzolsulfonyl-1,3-dihydro-indol-2-on, ihre Herstellung und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen
CA1213280A (fr)	1986-10-28	PROCEDE DE PREPARATION DE NOUVEAUX DERIVES DE 4-(1H- INDOL-3-YL) .alpha.-METHYL PIPERIDINE-1-ETHANOL ET DE LEURS SELS
EP0694536A1 (de)	1996-01-31	1-Benzyl-1,3-dihydro-2H-benzimidazol-2-one-Derivate, ihre Herstellung und diese enthaltende Zusammensetzungen
LU85191A1 (fr)	1984-10-24	Nouveaux derives de la benzo(g)quinoleine,leur preparation et leur utilisation comme medicaments
EP0004494B1 (de)	1982-02-17	1,3-Dihydro-3-(1-(2-(2,3-dihydro-1,4-benzodioxin-2-yl)2-hydroxy-äthyl)piperidin-4-yl)2H-indol-2-on Derivate, Verfahren zu ihrer Herstellung, ihre Verwendung als Arzneimittel und diese enthaltende pharmazeutische Zubereitungen
CA1095047A (fr)	1981-02-03	Procede de preparation de nouveaux derives du 1,4- benzodioxane
LU85725A1 (fr)	1985-10-22	Nouvelles 8alpha-acylaminoergolines,leur preparation et leur utilisation comme medicaments
EP0150139B1 (de)	1988-05-18	Indol-Ethylphenyl-Derivate, ihre Salze, Vefahren zur Herstellung, Anwendung als Heilmittel und Zusammensetzungen die sie enthalten
EP0747379A1 (de)	1996-12-11	Indol-, Indazol- und Benzisoxazolderivate zur Behandlung von Schizophrenia
FR2522658A1 (fr)	1983-09-09	Application a titre de medicaments de derives du trans 4-amino benz (c,d) indol-5-ol ainsi que de leurs sels, compositions les renfermant, nouveaux derives et leur procede de preparation
FR2753970A1 (fr)	1998-04-03	Derives de n-(benzothiazol-2-yl) piperidine-1-ethanamine, leur preparation et leur application en therapeutique
EP1828125B1 (de)	2008-04-09	Arylpiperazinderivate und deren verwendung als für den dopamin-d3-rezeptor selektive liganden
CA2378628C (fr)	2007-07-10	Nouveaux derives d'indenoindolones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
LU87047A1 (fr)	1988-06-13	Nouveaux derives de l'octahydrobenzo(g)quinoleene,leur preparation et leur utilisation comme medicaments
FR2547822A1 (fr)	1984-12-28	Acylpiperazinoquinazolines substituees utiles comme medicaments et procede pour leur preparation
EP0094305B1 (de)	1988-01-13	Derivate von 9-Oxalysergsäure, ihre Salze, Verfahren und Zwischenprodukte zu ihrer Herstellung, Verwendung als Arzneimittel und diese enthaltende Zusammensetzungen
EP0209435B1 (de)	1993-11-24	Hydroxyalkoxy-4-phenylpropylindolderivate, ihre Salze, Verfahren und Zwischenprodukte zur Herstellung, Anwendung als Heilmittel und Zusammensetzungen die sie enthalten
JPH0395161A (ja)	1991-04-19	（１，２，３，４―テトラヒドロ‐９‐アクリジンイミノ）シクロヘキサンカルボン酸および関連化合物
FR2539415A1 (fr)	1984-07-20	Derives de la d-2 imidazoline, leur preparation et leur application en therapeutique
LU86226A1 (fr)	1986-06-25	Nouvelles 8-acylaminoergolines,leur preparation,leur utilisation comme medicaments et les compositions pharmaceutiques les contenant
EP0433167B1 (de)	1994-03-02	Piperidinderivate, Verfahren zur Herstellung sowie diese enthaltende pharmazeutische Präparate
EP1119564B1 (de)	2002-12-18	Aryl-4-fluoro-4-(2-pyridin-2-yl-ethylamino)-methyl]-piperidin-1-yl-methanone derivate als 5-ht1-rezeptor-agonisten
EP0275221B1 (de)	1991-04-17	N-(1H-indol-4-yl)-Benzamidderivate, ihre Salze und deren Anwendung als Heilmittel und Zusammenstellungen, die sie enthalten
CA1161444A (fr)	1984-01-31	Procede de preparation de derives du cycloheptindolol et de leurs sels avec les acides