SK14482003A3 - Deriváty 6H-oxazolo[4,5-e]indolu ako ligandy nikotínacetyl- cholínového receptora a/alebo serotonergické ligandy, spôsob ich prípravy a ich použitie - Google Patents

Deriváty 6H-oxazolo[4,5-e]indolu ako ligandy nikotínacetyl- cholínového receptora a/alebo serotonergické ligandy, spôsob ich prípravy a ich použitie Download PDF

Info

Publication number: SK14482003A3
Authority: SK; Slovakia
Prior art keywords: oxazolo; indole; formula; solvates; azabicyclo
Prior art date: 2001-04-30

Application number

SK1448-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Kai Schiemann

Henning B�Ttcher

Joachim Leibrock

Original Assignee

Merck Patent Gmbh

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.)

2001-04-30

Filing date

2002-04-05

Publication date

2004-03-02

2002-04-05 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

2004-03-02 Publication of SK14482003A3 publication Critical patent/SK14482003A3/sk

Links

239000003446 ligand Substances 0.000 title claims abstract description 19
230000000862 serotonergic effect Effects 0.000 title claims abstract description 13
CIACKZWMHRQXBR-UHFFFAOYSA-N 6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical class N1C=CC2=C1C=CC1=C2N=CO1 CIACKZWMHRQXBR-UHFFFAOYSA-N 0.000 title claims description 17
102000019315 Nicotinic acetylcholine receptors Human genes 0.000 title abstract description 3
108050006807 Nicotinic acetylcholine receptors Proteins 0.000 title abstract description 3
150000001875 compounds Chemical class 0.000 claims abstract description 67
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims abstract description 22
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 21
238000011282 treatment Methods 0.000 claims abstract description 16
208000035475 disorder Diseases 0.000 claims abstract description 11
208000024827 Alzheimer disease Diseases 0.000 claims abstract description 9
206010012289 Dementia Diseases 0.000 claims abstract description 8
201000000980 schizophrenia Diseases 0.000 claims abstract description 8
229940076279 serotonin Drugs 0.000 claims abstract description 8
206010027175 memory impairment Diseases 0.000 claims abstract description 6
208000019901 Anxiety disease Diseases 0.000 claims abstract description 5
208000028017 Psychotic disease Diseases 0.000 claims abstract description 5
208000000323 Tourette Syndrome Diseases 0.000 claims abstract description 5
208000016620 Tourette disease Diseases 0.000 claims abstract description 5
208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 5
238000011321 prophylaxis Methods 0.000 claims abstract description 5
208000032841 Bulimia Diseases 0.000 claims abstract description 4
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206010036618 Premenstrual syndrome Diseases 0.000 claims abstract 2
-1 1-azabicyclo [2.2.2] oct-3-yl Chemical group 0.000 claims description 189
150000003839 salts Chemical class 0.000 claims description 71
239000012453 solvate Substances 0.000 claims description 26
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
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125000000753 cycloalkyl group Chemical group 0.000 claims description 13
125000000623 heterocyclic group Chemical group 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 13
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201000010099 disease Diseases 0.000 claims description 10
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UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
238000000034 method Methods 0.000 claims description 7
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
229920006395 saturated elastomer Polymers 0.000 claims description 6
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
239000013543 active substance Substances 0.000 claims description 5
125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 5
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
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125000003118 aryl group Chemical group 0.000 claims description 4
125000004197 benzothien-3-yl group Chemical group [H]C1=C(*)C2=C([H])C([H])=C([H])C([H])=C2S1 0.000 claims description 4
125000002619 bicyclic group Chemical group 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
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229910052731 fluorine Inorganic materials 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
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125000001624 naphthyl group Chemical group 0.000 claims description 4
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ZNJKKGYLILLJRG-UHFFFAOYSA-N 8-(1-azabicyclo[2.2.2]octan-3-yl)-2-[(5-methoxy-1h-indol-3-yl)methyl]-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1N(CC2)CCC2C1C1=CNC2=C1C(N=C(O1)CC3=CNC4=CC=C(C=C43)OC)=C1C=C2 ZNJKKGYLILLJRG-UHFFFAOYSA-N 0.000 claims description 3
CHGLCUWMBUYUCI-UHFFFAOYSA-N 8-(1-methylpiperidin-4-yl)-2-propyl-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound O1C(CCC)=NC(C2=3)=C1C=CC=3NC=C2C1CCN(C)CC1 CHGLCUWMBUYUCI-UHFFFAOYSA-N 0.000 claims description 3
PXYFHCRZTJGCCR-UHFFFAOYSA-N 8-piperidin-4-yl-2-(thiophen-2-ylmethyl)-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound N=1C(C=2C(C3CCNCC3)=CNC=2C=C2)=C2OC=1CC1=CC=CS1 PXYFHCRZTJGCCR-UHFFFAOYSA-N 0.000 claims description 3
230000036506 anxiety Effects 0.000 claims description 3
125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 3
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230000001105 regulatory effect Effects 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
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PXLIDIMHPNPGMH-UHFFFAOYSA-N sodium chromate Chemical compound [Na+].[Na+].[O-][Cr]([O-])(=O)=O PXLIDIMHPNPGMH-UHFFFAOYSA-N 0.000 description 1
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235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000008347 soybean phospholipid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
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239000005720 sucrose Substances 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular 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
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- 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
- A61P25/22—Anxiolytics
- 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
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Psychiatry (AREA)
Endocrinology (AREA)
Addiction (AREA)
Psychology (AREA)
Diabetes (AREA)
Hospice & Palliative Care (AREA)
Child & Adolescent Psychology (AREA)
Obesity (AREA)
Hematology (AREA)
Pain & Pain Management (AREA)
Nutrition Science (AREA)
Reproductive Health (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

SK1448-2003A 2001-04-30 2002-04-05 Deriváty 6H-oxazolo[4,5-e]indolu ako ligandy nikotínacetyl- cholínového receptora a/alebo serotonergické ligandy, spôsob ich prípravy a ich použitie SK14482003A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE10121217A DE10121217A1 (de)	2001-04-30	2001-04-30	6H-Oxazolo[4,5-e]indol-Derivate als nikotinische Acetylcholinrezeptor Liganden und/oder serotonerge Liganden
PCT/EP2002/003784 WO2002088139A1 (en)	2001-04-30	2002-04-05	6h-oxazolo[4,5-e]indole derivatives as nicotinic acetylcholine receptor ligands and/or serotonergic ligands

Publications (1)

Publication Number	Publication Date
SK14482003A3 true SK14482003A3 (sk)	2004-03-02

Family

ID=7683302

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1448-2003A SK14482003A3 (sk)	2001-04-30	2002-04-05	Deriváty 6H-oxazolo[4,5-e]indolu ako ligandy nikotínacetyl- cholínového receptora a/alebo serotonergické ligandy, spôsob ich prípravy a ich použitie

Country Status (13)

Country	Link
US (2)	US7291633B2 (de)
EP (1)	EP1392699B1 (de)
JP (1)	JP4485746B2 (de)
AR (1)	AR033267A1 (de)
AT (1)	ATE291026T1 (de)
AU (1)	AU2002257752B2 (de)
CA (1)	CA2445835C (de)
CZ (1)	CZ20033194A3 (de)
DE (2)	DE10121217A1 (de)
ES (1)	ES2239226T3 (de)
HU (1)	HUP0304034A2 (de)
SK (1)	SK14482003A3 (de)
WO (1)	WO2002088139A1 (de)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE10121217A1 (de) *	2001-04-30	2002-10-31	Merck Patent Gmbh	6H-Oxazolo[4,5-e]indol-Derivate als nikotinische Acetylcholinrezeptor Liganden und/oder serotonerge Liganden
JP2005530814A (ja) *	2002-05-30	2005-10-13	ニューロサーチ、アクティーゼルスカブ	３−置換されたキヌクリジン類及びその使用方法
WO2005041957A1 (en) *	2003-10-29	2005-05-12	Pfizer Products Inc.	Oxindole derivatives and their use as phosphodiesterase type 2 inhibitors
EP1937255A4 (de) *	2005-09-14	2013-06-26	Univ Witwatersrand Jhb	Pharmazeutische zusammensetzung
HUE043853T2 (hu)	2012-10-12	2019-09-30	Broad Inst Inc	GSK3 inhibitorok és eljárások azok alkalmazására
SG11201509370UA (en) *	2013-05-24	2015-12-30	Nestec Sa	Pathway specific assays for predicting irritable bowel syndrome diagnosis
AU2018249558A1 (en)	2017-04-05	2019-11-07	Biogen Ma Inc.	Tricyclic compounds as glycogen synthase kinase 3 (GSK3) inhibitors and uses thereof

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE69131123T2 (de)	1990-01-11	1999-09-30	Pharmacia & Upjohn Co., Kalamazoo	6,7,8,9-tetrahydro-3h-benz(e)indolheterocyclen mit wirkung auf das zentrale nervensystem
TW263508B (de) *	1991-02-12	1995-11-21	Pfizer
JP3155008B2 (ja)	1994-07-26	2001-04-09	ファイザー・インコーポレーテッド	セロトニンアゴニストおよびアンタゴニストとしての４−インドール誘導体
JPH11513391A (ja) *	1995-10-03	1999-11-16	ザスクリップスリサーチインスティテュート	Ｃｃ−１０６５及びズオカーマイシンのｃｂｉ類縁体
JP2002506069A (ja) *	1998-03-09	2002-02-26	ハー・ルンドベック・アクチエゼルスカベット	５−ヘテロアリール置換されたインドール類
DE10045112A1 (de) *	2000-09-11	2002-03-21	Merck Patent Gmbh	Verwendung von Indolderivaten zur Behandlung von Erkrankungen des zentralen Nervensystems
DE10121217A1 (de) *	2001-04-30	2002-10-31	Merck Patent Gmbh	6H-Oxazolo[4,5-e]indol-Derivate als nikotinische Acetylcholinrezeptor Liganden und/oder serotonerge Liganden

2001
- 2001-04-30 DE DE10121217A patent/DE10121217A1/de not_active Withdrawn
2002
- 2002-04-05 US US10/476,306 patent/US7291633B2/en not_active Expired - Fee Related
- 2002-04-05 AU AU2002257752A patent/AU2002257752B2/en not_active Ceased
- 2002-04-05 DE DE60203283T patent/DE60203283T2/de not_active Expired - Lifetime
- 2002-04-05 CZ CZ20033194A patent/CZ20033194A3/cs unknown
- 2002-04-05 WO PCT/EP2002/003784 patent/WO2002088139A1/en not_active Ceased
- 2002-04-05 JP JP2002585437A patent/JP4485746B2/ja not_active Expired - Fee Related
- 2002-04-05 HU HU0304034A patent/HUP0304034A2/hu unknown
- 2002-04-05 EP EP02727527A patent/EP1392699B1/de not_active Expired - Lifetime
- 2002-04-05 AT AT02727527T patent/ATE291026T1/de not_active IP Right Cessation
- 2002-04-05 ES ES02727527T patent/ES2239226T3/es not_active Expired - Lifetime
- 2002-04-05 CA CA2445835A patent/CA2445835C/en not_active Expired - Fee Related
- 2002-04-05 SK SK1448-2003A patent/SK14482003A3/sk unknown
- 2002-04-26 AR ARP020101530A patent/AR033267A1/es not_active Application Discontinuation
2007
- 2007-10-30 US US11/928,961 patent/US7741343B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
US20080051394A1 (en)	2008-02-28
EP1392699A1 (de)	2004-03-03
EP1392699B1 (de)	2005-03-16
JP4485746B2 (ja)	2010-06-23
ES2239226T3 (es)	2005-09-16
CA2445835A1 (en)	2002-11-07
WO2002088139A1 (en)	2002-11-07
HUP0304034A2 (hu)	2004-04-28
JP2004527562A (ja)	2004-09-09
AR033267A1 (es)	2003-12-10
DE60203283D1 (de)	2005-04-21
US7291633B2 (en)	2007-11-06
US7741343B2 (en)	2010-06-22
US20050101649A1 (en)	2005-05-12
CA2445835C (en)	2012-01-03
AU2002257752B2 (en)	2008-02-28
ATE291026T1 (de)	2005-04-15
DE60203283T2 (de)	2006-03-30
CZ20033194A3 (cs)	2004-02-18
DE10121217A1 (de)	2002-10-31

Publication	Publication Date	Title
AU617785B2 (en)	1991-12-05	Spirocyclic compounds incorporating five-membered rings with two heteroatoms
US7741343B2 (en)	2010-06-22	6H-oxazolo[4,5 e]indole derivatives as nicotinic acetylcholine receptor ligands and/or serotonergic ligands
BG64387B1 (bg)	2004-12-30	Халоген заместени тетрациклени производни на тетрахидрофуран
AU2003272316A1 (en)	2004-04-30	Antidepressant arylpiperazine derivatives of heterocycle-fused benzodioxans
DE68922478T2 (de)	1997-02-06	Pyrazoloisoquinoline-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen.
US7279496B2 (en)	2007-10-09	Dihydroimidazo[4,5-e]indole and 7h-pyrrolo[3,2-f]quinoxaline derivatives as nicotinic acetylcholine receptor ligands and/or serotonergic ligands
EP3083588A1 (de)	2016-10-26	Aromatische heterocyclische verbindungen und deren anwendung in pharmazeutika
AU2002310904A1 (en)	2003-04-17	Dihydroimidazo[4,5-e]indole and 7H-pyrrolo[3,2-f]quinoxaline derivatives as nicotinic acetylcholine receptor ligands and/or serotonergic ligands
AU2002257752A1 (en)	2003-04-17	6H-OXAZOLO[4,5-E]indole derivatives as nicotinic acetylcholine receptor ligands and/or serotonergic ligands
JPH01172386A (ja)	1989-07-07	カルボリン誘導体、その製造方法およびカルボリン誘導体を有効成分とする線維素溶解剤
US2933500A (en)	1960-04-19	Nu-aminoindolobenzoquinolizinium compounds
EP2516446B1 (de)	2014-08-13	Substituierte hexahydrochromeno[3,4-b]pyrrole mit affinität für die serotoninreceptor (5-ht)-familie
WO2025080608A9 (en)	2025-08-28	Desamide isotryptamine tetracycles for treating brain disorders
JP2004527534A (ja)	2004-09-09	ニコチン性アセチルコリン受容体リガンド