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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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
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Classifications

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- 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
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- 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
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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
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- 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
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- 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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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- A—HUMAN NECESSITIES
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
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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)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Psychiatry (AREA)
Endocrinology (AREA)
Psychology (AREA)
Addiction (AREA)
Diabetes (AREA)
Hospice & Palliative Care (AREA)
Pain & Pain Management (AREA)
Hematology (AREA)
Obesity (AREA)
Child & Adolescent Psychology (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Nutrition Science (AREA)
Reproductive Health (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
AU2003227522A1 (en) *	2002-05-30	2003-12-19	Neurosearch A/S	3-substituted quinuclidines and their use
WO2005041957A1 (en) *	2003-10-29	2005-05-12	Pfizer Products Inc.	Oxindole derivatives and their use as phosphodiesterase type 2 inhibitors
WO2007031846A2 (en) *	2005-09-14	2007-03-22	University Of The Witwatersrand, Johannesburg	Pharmaceutical composition
DK2909204T3 (en)	2012-10-12	2019-04-01	Broad Inst Inc	GSK3 INHIBITORS AND METHODS FOR USE THEREOF
CA2913108A1 (en) *	2013-05-24	2014-11-27	Nestec S.A.	Pathway specific assays for predicting irritable bowel syndrome diagnosis
KR20190136063A (ko) *	2017-04-05	2019-12-09	더 브로드 인스티튜트, 인코퍼레이티드	글리코겐 신타제 키나제 3 (gsk3) 억제제로서의 트리시클릭 화합물 및 그의 용도

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE178893T1 (de)	1990-01-11	1999-04-15	Upjohn Co	6,7,8,9-tetrahydro-3h-benz(e)indolheterocyclen mit wirkung auf das zentrale nervensystem
TW263508B (de)	1991-02-12	1995-11-21	Pfizer
CA2194984C (en) *	1994-07-26	2002-07-02	John Eugene Macor	4-indole derivatives as serotonin agonists and antagonists
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
DE69908330T2 (de) *	1998-03-09	2004-02-12	H. Lundbeck A/S	5-heteroaryl-substituierte indole
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 CA CA2445835A patent/CA2445835C/en not_active Expired - Fee Related
- 2002-04-05 US US10/476,306 patent/US7291633B2/en not_active Expired - Fee Related
- 2002-04-05 WO PCT/EP2002/003784 patent/WO2002088139A1/en not_active Ceased
- 2002-04-05 SK SK1448-2003A patent/SK14482003A3/sk unknown
- 2002-04-05 EP EP02727527A patent/EP1392699B1/de not_active Expired - Lifetime
- 2002-04-05 CZ CZ20033194A patent/CZ20033194A3/cs unknown
- 2002-04-05 DE DE60203283T patent/DE60203283T2/de not_active Expired - Lifetime
- 2002-04-05 AU AU2002257752A patent/AU2002257752B2/en not_active Ceased
- 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 JP JP2002585437A patent/JP4485746B2/ja not_active Expired - Fee Related
- 2002-04-05 HU HU0304034A patent/HUP0304034A2/hu 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
DE10121217A1 (de)	2002-10-31
JP2004527562A (ja)	2004-09-09
AR033267A1 (es)	2003-12-10
DE60203283T2 (de)	2006-03-30
ATE291026T1 (de)	2005-04-15
DE60203283D1 (de)	2005-04-21
US20050101649A1 (en)	2005-05-12
EP1392699B1 (de)	2005-03-16
US7291633B2 (en)	2007-11-06
EP1392699A1 (de)	2004-03-03
AU2002257752B2 (en)	2008-02-28
WO2002088139A1 (en)	2002-11-07
JP4485746B2 (ja)	2010-06-23
ES2239226T3 (es)	2005-09-16
CZ20033194A3 (cs)	2004-02-18
CA2445835A1 (en)	2002-11-07
HUP0304034A2 (hu)	2004-04-28
CA2445835C (en)	2012-01-03
US7741343B2 (en)	2010-06-22

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
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
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
WO2025080608A9 (en)	2025-08-28	Desamide isotryptamine tetracycles for treating brain disorders
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
JP2004527534A (ja)	2004-09-09	ニコチン性アセチルコリン受容体リガンド
HK1174918B (en)	2015-07-24	Substituted hexahydrochromeno[3,4-b]pyrroles with affinity for the serotonin receptor (5-ht) family