NO323209B1 - 5-aminoalkyl og 5-aminokarbonylsubstituerte indoler, deres anvendelse og farmasoytiske sammensetninger inneholdende det samme, samt fremstilling av radiomerkede forbindelser - Google Patents

5-aminoalkyl og 5-aminokarbonylsubstituerte indoler, deres anvendelse og farmasoytiske sammensetninger inneholdende det samme, samt fremstilling av radiomerkede forbindelser Download PDF

Info

Publication number: NO323209B1
Authority: NO; Norway
Prior art keywords: fluorophenyl; ethyl; piperidinyl; compound according; indole
Prior art date: 1999-09-09

Application number

NO20021162A

Other languages

English (en)

Norwegian (no)

Other versions

NO20021162L (no

NO20021162D0 (no

Inventor

Jens Kristian Perregaard

Kim Andersen

Thomas Balle

Original Assignee

Lundbeck & Co As H

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.)

1999-09-09

Filing date

2002-03-08

Publication date

2007-01-22

2002-03-08 Application filed by Lundbeck & Co As H filed Critical Lundbeck & Co As H

2002-03-08 Publication of NO20021162D0 publication Critical patent/NO20021162D0/no

2002-05-08 Publication of NO20021162L publication Critical patent/NO20021162L/no

2007-01-22 Publication of NO323209B1 publication Critical patent/NO323209B1/no

Links

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239000002243 precursor Substances 0.000 claims description 6
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ZFXYFBGIUFBOJW-UHFFFAOYSA-N Theophylline Natural products O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
239000000951 adrenergic alpha-1 receptor antagonist Substances 0.000 description 1
239000000556 agonist Substances 0.000 description 1
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150000001298 alcohols Chemical class 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
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238000005804 alkylation reaction Methods 0.000 description 1
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230000036506 anxiety Effects 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000006254 arylation reaction Methods 0.000 description 1
239000002585 base Substances 0.000 description 1
125000005605 benzo group Chemical group 0.000 description 1
238000004166 bioassay Methods 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
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210000005013 brain tissue Anatomy 0.000 description 1
239000012267 brine Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000003857 carboxamides Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001793 charged compounds Chemical class 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000011260 co-administration Methods 0.000 description 1
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238000007796 conventional method Methods 0.000 description 1
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210000005257 cortical tissue Anatomy 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000003210 dopamine receptor blocking agent Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000011049 filling Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000010304 firing Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 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
238000010438 heat treatment Methods 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
150000002475 indoles Chemical class 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
INQOMBQAUSQDDS-BJUDXGSMSA-N iodomethane Chemical compound I[11CH3] INQOMBQAUSQDDS-BJUDXGSMSA-N 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
239000008101 lactose Substances 0.000 description 1
238000005567 liquid scintillation counting Methods 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
OIRDBPQYVWXNSJ-UHFFFAOYSA-N methyl trifluoromethansulfonate Chemical compound COS(=O)(=O)C(F)(F)F OIRDBPQYVWXNSJ-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 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
210000002569 neuron Anatomy 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
UWBHMRBRLOJJAA-UHFFFAOYSA-N oxaluric acid Chemical compound NC(=O)NC(=O)C(O)=O UWBHMRBRLOJJAA-UHFFFAOYSA-N 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000002953 preparative HPLC Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
230000001003 psychopharmacologic effect Effects 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical group CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000000527 sonication Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
DKGZKTPJOSAWFA-UHFFFAOYSA-N spiperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 DKGZKTPJOSAWFA-UHFFFAOYSA-N 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
201000009032 substance abuse Diseases 0.000 description 1
231100000736 substance abuse Toxicity 0.000 description 1
208000011117 substance-related disease Diseases 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
230000005062 synaptic transmission Effects 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
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000003325 tomography Methods 0.000 description 1
230000001256 tonic effect Effects 0.000 description 1
231100000027 toxicology Toxicity 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
- 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
- A61P25/24—Antidepressants
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Epidemiology (AREA)
Psychiatry (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pain & Pain Management (AREA)
Urology & Nephrology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Indole Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

NO20021162A 1999-09-09 2002-03-08 5-aminoalkyl og 5-aminokarbonylsubstituerte indoler, deres anvendelse og farmasoytiske sammensetninger inneholdende det samme, samt fremstilling av radiomerkede forbindelser NO323209B1 (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US15346099P	1999-09-09	1999-09-09
DKPA199901273		1999-09-09
PCT/DK2000/000496 WO2001021614A1 (en)	1999-09-09	2000-09-08	5-aminoalkyl and 5-aminocarbonyl substituted indoles

Publications (3)

Publication Number	Publication Date
NO20021162D0 NO20021162D0 (no)	2002-03-08
NO20021162L NO20021162L (no)	2002-05-08
NO323209B1 true NO323209B1 (no)	2007-01-22

Family

ID=26065506

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20021162A NO323209B1 (no)	1999-09-09	2002-03-08	5-aminoalkyl og 5-aminokarbonylsubstituerte indoler, deres anvendelse og farmasoytiske sammensetninger inneholdende det samme, samt fremstilling av radiomerkede forbindelser

Country Status (10)

Country	Link
US (1)	US6833376B2 (de)
EP (1)	EP1214312B1 (de)
JP (1)	JP2003509509A (de)
AT (1)	ATE264320T1 (de)
AU (1)	AU6984600A (de)
DE (1)	DE60009932T2 (de)
ES (1)	ES2219385T3 (de)
NO (1)	NO323209B1 (de)
PT (1)	PT1214312E (de)
WO (1)	WO2001021614A1 (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2477074A1 (en) *	2002-02-22	2003-08-28	H. Lundbeck A/S	5-heteroaryl substituted indoles
WO2005111028A1 (en) *	2004-05-03	2005-11-24	Janssen Pharmaceutica N.V.	Novel indole derivatives as selective androgen receptor modulators (sarms)

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH05505612A (ja) *	1991-03-01	1993-08-19	ハー・ルンドベック・アクティーゼルスカブ	高血圧症及び末梢血管疾患の治療法
DK123493D0 (da) *	1993-11-01	1993-11-01	Lundbeck & Co As H	Compounds
US5521196A (en) *	1994-10-05	1996-05-28	Eli Lilly And Company	5-HT1F agonists for the treatment of migraine
DE19500689A1 (de) *	1995-01-12	1996-07-18	Merck Patent Gmbh	Indolpiperidin-Derivate
KR19980703048A (ko) *	1995-03-20	1998-09-05	피터쥐.스트링거	5-치환-3-(1,2,3,6-테트라히드로피리딘-4-일)- 및 3-(피페리딘-4-일)-1ｈ-인돌: 신규한 5-ｈｔ1ｆ 아고니스트
DE19602505A1 (de) *	1996-01-25	1997-07-31	Merck Patent Gmbh	1-(Pyrazol-4-Indol-3-yl)-Piperidine
DE69908330T2 (de) *	1998-03-09	2004-02-12	H. Lundbeck A/S	5-heteroaryl-substituierte indole

2000
- 2000-09-08 JP JP2001524991A patent/JP2003509509A/ja active Pending
- 2000-09-08 ES ES00958270T patent/ES2219385T3/es not_active Expired - Lifetime
- 2000-09-08 EP EP00958270A patent/EP1214312B1/de not_active Expired - Lifetime
- 2000-09-08 PT PT00958270T patent/PT1214312E/pt unknown
- 2000-09-08 WO PCT/DK2000/000496 patent/WO2001021614A1/en not_active Ceased
- 2000-09-08 AU AU69846/00A patent/AU6984600A/en not_active Abandoned
- 2000-09-08 AT AT00958270T patent/ATE264320T1/de not_active IP Right Cessation
- 2000-09-08 DE DE60009932T patent/DE60009932T2/de not_active Expired - Fee Related
2002
- 2002-03-08 US US10/097,126 patent/US6833376B2/en not_active Expired - Fee Related
- 2002-03-08 NO NO20021162A patent/NO323209B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
PT1214312E (pt)	2004-08-31
EP1214312B1 (de)	2004-04-14
WO2001021614A1 (en)	2001-03-29
NO20021162L (no)	2002-05-08
AU6984600A (en)	2001-04-24
DE60009932T2 (de)	2005-04-14
DE60009932D1 (de)	2004-05-19
EP1214312A1 (de)	2002-06-19
NO20021162D0 (no)	2002-03-08
ATE264320T1 (de)	2004-04-15
JP2003509509A (ja)	2003-03-11
US20020169169A1 (en)	2002-11-14
ES2219385T3 (es)	2004-12-01
US6833376B2 (en)	2004-12-21

Legal Events

Date	Code	Title	Description
2010-04-26	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
EP0465398B1 (de)	1994-12-14	Neue Indolderivate
CZ288351B6 (en)	2001-05-16	Nitrogenous heterocyclic compound, process of its preparation and use as well as a medicament containing thereof
KR100233955B1 (ko)	2000-02-01	신규 3-아릴인돌 및 3-아릴인다졸 유도체
JP2003521443A (ja)	2003-07-15	４，５，６及び７−インドール及びインドリン誘導体、その製造方法及びその使用方法
JP2004516321A (ja)	2004-06-03	精神医学及び神経障害の治療に有用な３−インドリン誘導体
SK280881B6 (sk)	2000-08-14	Derivát 3-indolylpiperidínu, spôsob jeho prípravy, jeho použitie na prípravu farmaceutického prostriedku a farmaceutický prostriedok, ktorý ho obsahuje
CZ20022319A3 (cs)	2002-10-16	Substituovaná fenylpiperazinová sloučenina a farmaceutický prostředek, který ji obsahuje
US7105543B2 (en)	2006-09-12	4-, 5-, 6- and 7-indole derivatives useful for the treatment of CNS disorders
FR2758327A1 (fr)	1998-07-17	Nouvelles arylpiperazines derivees de piperidine
JP3898219B2 (ja)	2007-03-28	フエニルインドール化合物
JP2004503550A (ja)	2004-02-05	Ｃｎｓ障害の治療に有用なインドール誘導体
US6391882B1 (en)	2002-05-21	4,5,6 and 7-indole and indoline derivatitives, their preparation and use
US6833376B2 (en)	2004-12-21	5-aminoalkyl and 5-aminocarbonyl substituted indoles
US6602889B1 (en)	2003-08-05	5-heteroaryl substituted indoles
NO323799B1 (no)	2007-07-09	Indolderivater, farmasoytisk sammensetning inneholdende dem og deres anvendelse.
CN101243075A (zh)	2008-08-13	新颖的2,3-二氢吲哚化合物
JP2004501151A (ja)	2004-01-15	Ｃｎｓ障害の治療に有用なインドール誘導体
EP1468996B1 (de)	2007-09-26	Indolderivate zur Behandlung von Erkrankungen des Zentralnervensystems
NO318610B1 (no)	2005-04-18	Indol og 2,3-dihydroindolderivater, deres fremstilling og anvendelse
MXPA00012609A (en)	2001-07-31	4,5,6 and 7-indole and indoline derivatives, their preparation and use
HK1059438B (en)	2006-10-20	4-, 5-, 6- and 7-indole derivatives useful for the treatment of cns disorders