SK9342003A3 - 3-Indoline derivatives useful in the treatment of psychiatric and neurologic disorders - Google Patents

3-Indoline derivatives useful in the treatment of psychiatric and neurologic disorders Download PDF

Info

Publication number: SK9342003A3
Authority: SK; Slovakia
Prior art keywords: alkyl; acetyl; hydrogen; dihydro; cycloalkyl
Prior art date: 2000-12-22

Application number

SK934-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Jan Kehler

Benny Bang-Andersen

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.)

2000-12-22

Filing date

2001-12-18

Publication date

2003-10-07

2001-12-18 Application filed by Lundbeck & Co As H filed Critical Lundbeck & Co As H

2003-10-07 Publication of SK9342003A3 publication Critical patent/SK9342003A3/sk

Links

238000011282 treatment Methods 0.000 title claims abstract description 23
208000020016 psychiatric disease Diseases 0.000 title abstract description 4
208000012902 Nervous system disease Diseases 0.000 title abstract description 3
150000001875 compounds Chemical class 0.000 claims abstract description 72
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 43
239000001257 hydrogen Substances 0.000 claims abstract description 42
150000002431 hydrogen Chemical class 0.000 claims abstract description 19
150000003839 salts Chemical class 0.000 claims abstract description 13
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 12
229910052736 halogen Inorganic materials 0.000 claims abstract description 12
150000002367 halogens Chemical group 0.000 claims abstract description 12
208000028017 Psychotic disease Diseases 0.000 claims abstract description 11
125000002252 acyl group Chemical group 0.000 claims abstract description 11
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims abstract description 11
239000002253 acid Substances 0.000 claims abstract description 10
239000003814 drug Substances 0.000 claims abstract description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 10
125000003118 aryl group Chemical group 0.000 claims abstract description 9
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 8
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract description 6
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 6
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 6
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims abstract description 5
238000004519 manufacturing process Methods 0.000 claims abstract description 5
125000003441 thioacyl group Chemical group 0.000 claims abstract description 5
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims abstract description 4
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical group C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims abstract description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
125000003386 piperidinyl group Chemical group 0.000 claims abstract description 4
125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 4
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 5
125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims abstract 3
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 2
125000000217 alkyl group Chemical group 0.000 claims description 45
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
230000000694 effects Effects 0.000 claims description 19
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208000019901 Anxiety disease Diseases 0.000 claims description 15
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
208000019695 Migraine disease Diseases 0.000 claims description 11
208000024891 symptom Diseases 0.000 claims description 11
206010027599 migraine Diseases 0.000 claims description 10
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 9
125000003342 alkenyl group Chemical group 0.000 claims description 9
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
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230000016571 aggressive behavior Effects 0.000 claims description 7
125000000304 alkynyl group Chemical group 0.000 claims description 7
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125000003545 alkoxy group Chemical group 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
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PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
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229910052731 fluorine Inorganic materials 0.000 claims description 3
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VIHFYGJNDLKWET-UHFFFAOYSA-N 1-[3-[2-[4-(3,4-dichlorophenyl)piperidin-1-yl]ethyl]-2,3-dihydroindol-1-yl]ethanone Chemical compound C12=CC=CC=C2N(C(=O)C)CC1CCN(CC1)CCC1C1=CC=C(Cl)C(Cl)=C1 VIHFYGJNDLKWET-UHFFFAOYSA-N 0.000 claims 2
UBCONEKRLSAWBT-UHFFFAOYSA-N 1-[3-[2-[4-(3,4-dimethylphenyl)piperazin-1-yl]ethyl]-2,3-dihydroindol-1-yl]ethanone Chemical compound C12=CC=CC=C2N(C(=O)C)CC1CCN(CC1)CCN1C1=CC=C(C)C(C)=C1 UBCONEKRLSAWBT-UHFFFAOYSA-N 0.000 claims 2
JMCBHCLPCVFMFE-UHFFFAOYSA-N 1-[3-[2-[4-(4-bromophenyl)piperazin-1-yl]ethyl]-2,3-dihydroindol-1-yl]ethanone Chemical compound C12=CC=CC=C2N(C(=O)C)CC1CCN(CC1)CCN1C1=CC=C(Br)C=C1 JMCBHCLPCVFMFE-UHFFFAOYSA-N 0.000 claims 2
JEKSUNRNVHPMLN-UHFFFAOYSA-N 1-[3-[2-[4-(4-methylphenyl)piperazin-1-yl]ethyl]-2,3-dihydroindol-1-yl]ethanone Chemical compound C12=CC=CC=C2N(C(=O)C)CC1CCN(CC1)CCN1C1=CC=C(C)C=C1 JEKSUNRNVHPMLN-UHFFFAOYSA-N 0.000 claims 1
230000001149 cognitive effect Effects 0.000 claims 1
208000035475 disorder Diseases 0.000 claims 1
125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 1
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
125000006621 (C3-C8) cycloalkyl-(C1-C6) alkyl group Chemical group 0.000 abstract description 4
229910052799 carbon Inorganic materials 0.000 abstract description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 4
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 32
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239000000203 mixture Substances 0.000 description 16
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238000000034 method Methods 0.000 description 13
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 8
150000001412 amines Chemical class 0.000 description 7
239000005557 antagonist Substances 0.000 description 7
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
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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 5
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BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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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
- C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
- A—HUMAN NECESSITIES
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical

Landscapes

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

SK934-2003A 2000-12-22 2001-12-18 3-Indoline derivatives useful in the treatment of psychiatric and neurologic disorders SK9342003A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DKPA200001931		2000-12-22
PCT/DK2001/000835 WO2002051833A1 (en)	2000-12-22	2001-12-18	3-indoline derivatives useful in the treatment of psychiatric and neurologic disorders

Publications (1)

Publication Number	Publication Date
SK9342003A3 true SK9342003A3 (en)	2003-10-07

Family

ID=8159925

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK934-2003A SK9342003A3 (en)	2000-12-22	2001-12-18	3-Indoline derivatives useful in the treatment of psychiatric and neurologic disorders

Country Status (20)

Country	Link
US (1)	US20040044007A1 (cs)
EP (1)	EP1345921A1 (cs)
JP (1)	JP2004516321A (cs)
KR (1)	KR20030063455A (cs)
CN (1)	CN1491223A (cs)
AR (1)	AR035521A1 (cs)
BG (1)	BG107982A (cs)
BR (1)	BR0116365A (cs)
CA (1)	CA2432473A1 (cs)
CZ (1)	CZ20032004A3 (cs)
EA (1)	EA200300718A1 (cs)
HU (1)	HUP0500350A2 (cs)
IL (1)	IL156340A0 (cs)
IS (1)	IS6837A (cs)
MX (1)	MXPA03005555A (cs)
NO (1)	NO20032636D0 (cs)
PL (1)	PL362133A1 (cs)
SK (1)	SK9342003A3 (cs)
WO (1)	WO2002051833A1 (cs)
ZA (1)	ZA200304643B (cs)

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WO2009123714A2 (en)	2008-04-02	2009-10-08	Arena Pharmaceuticals, Inc.	Processes for the preparation of pyrazole derivatives useful as modulators of the 5-ht2a serotonin receptor
KR101062376B1 (ko) *	2008-04-10	2011-09-06	한국화학연구원	신규 인돌 카르복실산 비스피리딜 카르복사마이드 유도체,이의 제조방법 및 이를 유효성분으로 함유하는 조성물
US9126946B2 (en)	2008-10-28	2015-09-08	Arena Pharmaceuticals, Inc.	Processes useful for the preparation of 1-[3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenyl]-3-(2,4-difluoro-phenyl)urea and crystalline forms related thereto
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2001
- 2001-12-17 AR ARP010105843A patent/AR035521A1/es not_active Application Discontinuation
- 2001-12-18 CA CA002432473A patent/CA2432473A1/en not_active Abandoned
- 2001-12-18 KR KR10-2003-7008437A patent/KR20030063455A/ko not_active Withdrawn
- 2001-12-18 CN CNA018227481A patent/CN1491223A/zh active Pending
- 2001-12-18 SK SK934-2003A patent/SK9342003A3/sk unknown
- 2001-12-18 WO PCT/DK2001/000835 patent/WO2002051833A1/en not_active Ceased
- 2001-12-18 ZA ZA200304643A patent/ZA200304643B/en unknown
- 2001-12-18 CZ CZ20032004A patent/CZ20032004A3/cs unknown
- 2001-12-18 EP EP01271969A patent/EP1345921A1/en not_active Withdrawn
- 2001-12-18 JP JP2002552928A patent/JP2004516321A/ja not_active Withdrawn
- 2001-12-18 BR BR0116365-5A patent/BR0116365A/pt not_active Application Discontinuation
- 2001-12-18 EA EA200300718A patent/EA200300718A1/ru unknown
- 2001-12-18 MX MXPA03005555A patent/MXPA03005555A/es unknown
- 2001-12-18 HU HU0500350A patent/HUP0500350A2/hu unknown
- 2001-12-18 IL IL15634001A patent/IL156340A0/xx unknown
- 2001-12-18 PL PL36213301A patent/PL362133A1/xx unknown
2003
- 2003-06-05 IS IS6837A patent/IS6837A/is unknown
- 2003-06-11 NO NO20032636A patent/NO20032636D0/no not_active Application Discontinuation
- 2003-06-17 US US10/601,347 patent/US20040044007A1/en not_active Abandoned
- 2003-07-08 BG BG107982A patent/BG107982A/bg unknown

Also Published As

Publication number	Publication date
MXPA03005555A (es)	2004-03-26
IS6837A (is)	2003-06-05
US20040044007A1 (en)	2004-03-04
ZA200304643B (en)	2004-07-19
BG107982A (bg)	2004-08-31
CZ20032004A3 (cs)	2003-10-15
IL156340A0 (en)	2004-01-04
KR20030063455A (ko)	2003-07-28
PL362133A1 (en)	2004-10-18
JP2004516321A (ja)	2004-06-03
HUP0500350A2 (hu)	2005-08-29
BR0116365A (pt)	2004-07-06
NO20032636L (no)	2003-06-11
WO2002051833A1 (en)	2002-07-04
AR035521A1 (es)	2004-06-02
EP1345921A1 (en)	2003-09-24
CN1491223A (zh)	2004-04-21
NO20032636D0 (no)	2003-06-11
CA2432473A1 (en)	2002-07-04
EA200300718A1 (ru)	2003-10-30

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SK11062002A3 (sk)	2002-12-03	Fenylpiperazínové deriváty, farmaceutický prostriedok s ich obsahom a ich použitie
SK9442002A3 (en)	2002-11-06	Substituted phenyl-piperazine derivatives, their preparation and use
US7223765B2 (en)	2007-05-29	4-phenyl-1-piperazinyl, -piperidinyl and -tetrahydropyridyl derivatives
EP1309586B1 (en)	2006-03-22	4-, 5-, 6- and 7-indole derivatives useful for the treatment of cns disorders
HU201543B (en)	1990-11-28	Process for production of derivatives of 2-(/piperin-4-il/-methil/)-1,2,3,4-tetrahydro-izoquinoline and medical compositions containing them
SK9452002A3 (en)	2002-11-06	Indole derivatives, pharmaceutical composition containing the same and their use
DE60130691T2 (de)	2008-07-17	Indolderivate zur Behandlung von Erkrankungen des Zentralnervensystems
SK1092003A3 (en)	2003-05-02	Indole derivatives useful for the treatment of CNS disorders
EP1299384B1 (en)	2004-03-24	Indole derivatives useful for the treatment of cns disorders
CN101243075A (zh)	2008-08-13	新颖的2,3-二氢吲哚化合物
AU2002221576A1 (en)	2002-07-08	3-indoline derivatives useful in the treatment of psychiatric and neurologic disorders
SK512003A3 (en)	2003-05-02	Indole derivatives useful for the treatment of CNS disorders
SK402003A3 (en)	2003-07-01	Indole derivatives, pharmaceutical composition comprising same and their use
HK1123550A (en)	2009-06-19	Novel 2,3-dihydroindole compounds
MXPA02012149A (en)	2008-10-03	Indole derivatives useful for the treatment of cns disorders