UA74837C2 - 4-, 5-, 6- and 7-methylene substituted indole derivatives being useful for the treatment of cns disorders, a pharmaceutical composition and a method for treatment - Google Patents

4-, 5-, 6- and 7-methylene substituted indole derivatives being useful for the treatment of cns disorders, a pharmaceutical composition and a method for treatment Download PDF

Info

Publication number: UA74837C2
Authority: UA; Ukraine
Prior art keywords: indole; piperazin; alkyl; methyl; compound according
Prior art date: 2000-08-18

Application number

UA2003010504A

Other languages

English (en)

Ukrainian (uk)

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.)

2000-08-18

Filing date

2001-08-17

Publication date

2006-02-15

2001-08-17 Application filed by Lundbeck & Co As H filed Critical Lundbeck & Co As H

2006-02-15 Publication of UA74837C2 publication Critical patent/UA74837C2/uk

Links

238000000034 method Methods 0.000 title claims description 13
239000008194 pharmaceutical composition Substances 0.000 title claims description 4
229940054051 antipsychotic indole derivative Drugs 0.000 title description 2
150000002475 indoles Chemical class 0.000 title 1
-1 Ñ1-6-alkylsulfonyl Chemical group 0.000 claims abstract description 105
150000001875 compounds Chemical class 0.000 claims abstract description 64
125000002252 acyl group Chemical group 0.000 claims abstract description 13
229910052736 halogen Inorganic materials 0.000 claims abstract description 12
150000002367 halogens Chemical class 0.000 claims abstract description 12
125000001424 substituent group Chemical group 0.000 claims abstract description 11
125000003118 aryl group Chemical group 0.000 claims abstract description 10
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims abstract description 10
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
239000001257 hydrogen Substances 0.000 claims abstract description 9
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 9
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 8
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 8
125000001041 indolyl group Chemical group 0.000 claims abstract description 7
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 43
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 21
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 11
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
201000000980 schizophrenia Diseases 0.000 claims description 8
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239000003085 diluting agent Substances 0.000 claims description 5
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 5
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 5
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229960003638 dopamine Drugs 0.000 abstract description 22
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OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 2
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HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical class C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 description 2
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CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical class [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
229910000086 alane Inorganic materials 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
230000008485 antagonism Effects 0.000 description 2
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210000004556 brain Anatomy 0.000 description 2
QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 description 2
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238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
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125000005843 halogen group Chemical group 0.000 description 1
210000002837 heart atrium Anatomy 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
IENZCGNHSIMFJE-UHFFFAOYSA-N indole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2NC=CC2=C1 IENZCGNHSIMFJE-UHFFFAOYSA-N 0.000 description 1
230000010354 integration Effects 0.000 description 1
230000003993 interaction Effects 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
238000004255 ion exchange chromatography Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 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
125000001786 isothiazolyl group Chemical group 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
230000010534 mechanism of action Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000012528 membrane Substances 0.000 description 1
230000003340 mental effect Effects 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
229960002216 methylparaben Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 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
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
UNEIHNMKASENIG-UHFFFAOYSA-N para-chlorophenylpiperazine Chemical compound C1=CC(Cl)=CC=C1N1CCNCC1 UNEIHNMKASENIG-UHFFFAOYSA-N 0.000 description 1
WUHLVXDDBHWHLQ-UHFFFAOYSA-N pentazole Chemical compound N=1N=NNN=1 WUHLVXDDBHWHLQ-UHFFFAOYSA-N 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
229940069328 povidone Drugs 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
208000020016 psychiatric disease Diseases 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000005932 reductive alkylation reaction Methods 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 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
239000000932 sedative agent Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
238000004544 sputter deposition Methods 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 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
125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
229910052722 tritium Inorganic materials 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- C07D401/06—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
- 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
- A61P25/06—Antimigraine agents
- 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
- 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
- A61P25/28—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
- 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
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

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

UA2003010504A 2000-08-18 2001-08-17 4-, 5-, 6- and 7-methylene substituted indole derivatives being useful for the treatment of cns disorders, a pharmaceutical composition and a method for treatment UA74837C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DKPA200001229		2000-08-18
PCT/DK2001/000547 WO2002016349A1 (fr)	2000-08-18	2001-08-17	Derives 4-, 5-, 6- et 7-indoliques utiles dans le traitement de troubles du systeme nerveux central

Publications (1)

Publication Number	Publication Date
UA74837C2 true UA74837C2 (en)	2006-02-15

Family

ID=8159658

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2003010504A UA74837C2 (en)	2000-08-18	2001-08-17	4-, 5-, 6- and 7-methylene substituted indole derivatives being useful for the treatment of cns disorders, a pharmaceutical composition and a method for treatment

Country Status (29)

Country	Link
US (2)	US6958338B2 (fr)
EP (1)	EP1309586B1 (fr)
JP (1)	JP2004506731A (fr)
KR (1)	KR20030022363A (fr)
CN (1)	CN1243750C (fr)
AR (1)	AR030357A1 (fr)
AT (1)	ATE321040T1 (fr)
AU (2)	AU7961101A (fr)
BG (1)	BG107611A (fr)
BR (1)	BR0113452A (fr)
CA (1)	CA2419266A1 (fr)
CZ (1)	CZ2003461A3 (fr)
DE (1)	DE60118205T2 (fr)
DK (1)	DK1309586T3 (fr)
EA (1)	EA006155B1 (fr)
ES (1)	ES2257424T3 (fr)
HR (1)	HRP20030052A2 (fr)
HU (1)	HUP0302777A2 (fr)
IL (1)	IL154051A0 (fr)
IS (1)	IS6694A (fr)
MX (1)	MXPA03000838A (fr)
NO (1)	NO20030522L (fr)
NZ (1)	NZ523786A (fr)
PL (1)	PL363309A1 (fr)
PT (1)	PT1309586E (fr)
SK (1)	SK3212003A3 (fr)
UA (1)	UA74837C2 (fr)
WO (1)	WO2002016349A1 (fr)
ZA (1)	ZA200300562B (fr)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP2520567A3 (fr) *	2006-02-23	2012-12-12	Shionogi & Co., Ltd.	Dérivés d'hétérocycle contenant de l'azote substitués avec un groupe cyclique
NZ611485A (en)	2006-04-07	2014-09-26	Vertex Pharma	Modulators of atp-binding cassette transporters
US10022352B2 (en)	2006-04-07	2018-07-17	Vertex Pharmaceuticals Incorporated	Modulators of ATP-binding cassette transporters
US7645789B2 (en)	2006-04-07	2010-01-12	Vertex Pharmaceuticals Incorporated	Indole derivatives as CFTR modulators
USRE50453E1 (en)	2006-04-07	2025-06-10	Vertex Pharmaceuticals Incorporated	Indole derivatives as CFTR modulators
US8563573B2 (en)	2007-11-02	2013-10-22	Vertex Pharmaceuticals Incorporated	Azaindole derivatives as CFTR modulators
TWI404702B (zh) *	2007-08-31	2013-08-11	Lundbeck & Co As H	兒茶酚胺衍生物和其前藥
US8802868B2 (en)	2010-03-25	2014-08-12	Vertex Pharmaceuticals Incorporated	Solid forms of (R)-1(2,2-difluorobenzo[D][1,3]dioxo1-5-yl)-N-(1-(2,3-dihydroxypropyl-6-fluoro-2-(1-hydroxy-2-methylpropan2-yl)-1H-Indol-5-yl)-Cyclopropanecarboxamide
SG10201913594UA (en)	2010-04-22	2020-02-27	Vertex Pharma	Process of producing cycloalkylcarboxamido-indole compounds
AU2013290444B2 (en)	2012-07-16	2018-04-26	Vertex Pharmaceuticals Incorporated	Pharmaceutical compositions of (R)-1-(2,2-diflurorbenzo[d][1,3]dioxol-5-yl)-N-(1-(2,3-dihydroxypropyl)-6-fluoro-2-(1-hydroxy-2-methylpropan-2-yl)-1H-indol-5-yl) cyclopropanecarboxamide and administration thereof
JO3425B1 (ar)	2013-07-15	2019-10-20	Novartis Ag	مشتقات البابيريدينيل-اندول واستخدامها كعامل متمم لمثبطات b
MX387720B (es)	2014-04-15	2025-03-12	Vertex Pharma	Composiciones farmacéuticas para el tratamiento de enfermedades mediadas por el regulador de conductancia de transmembrana de fibrosis quística.

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Publication number	Priority date	Publication date	Assignee	Title
DE3421641A1 (de) *	1984-06-09	1985-12-12	Merck Patent Gmbh, 6100 Darmstadt	Indolderivate
MX173362B (es) *	1987-03-02	1994-02-23	Pfizer	Compuestos de piperazinil heterociclicos y procedimiento para su preparacion
US4831031A (en) *	1988-01-22	1989-05-16	Pfizer Inc.	Aryl piperazinyl-(C2 or C4) alkylene heterocyclic compounds having neuroleptic activity
AU6215594A (en) *	1993-03-18	1994-10-11	Merck Sharp & Dohme Limited	Indole derivatives as dopamine d4 antagonists
WO1995029911A1 (fr) *	1994-04-28	1995-11-09	Merck Sharp & Dohme Limited	Derives de benzofurane utilises comme antagonistes du recepteur d¿4?
DE19500689A1 (de) *	1995-01-12	1996-07-18	Merck Patent Gmbh	Indolpiperidin-Derivate
GB9520731D0 (en) *	1995-10-10	1995-12-13	Merck Sharp & Dohme	Therapeutic agents
GB9604036D0 (en) *	1996-02-26	1996-04-24	Merck Sharp & Dohme	Therapeutic agents
WO1999037304A1 (fr) *	1998-01-27	1999-07-29	Aventis Pharmaceuticals Products Inc.	COMPOSES OXOAZAHETEROCYCLYLE SUBSTITUES INHIBITEURS DU FACTEUR Xa
TR200201051T2 (tr) *	1999-10-19	2002-09-23	Merck & Co., Inc.	Tirosin kinaz inhibitörleri.
US6727264B1 (en) *	2001-07-05	2004-04-27	Synaptic Pharmaceutical Corporation	Substituted anilinic piperidines as MCH selective antagonists

2001
- 2001-08-15 AR ARP010103899A patent/AR030357A1/es not_active Application Discontinuation
- 2001-08-17 AU AU7961101A patent/AU7961101A/xx active Pending
- 2001-08-17 HR HR20030052A patent/HRP20030052A2/xx not_active Application Discontinuation
- 2001-08-17 CN CNB018142400A patent/CN1243750C/zh not_active Expired - Fee Related
- 2001-08-17 WO PCT/DK2001/000547 patent/WO2002016349A1/fr not_active Ceased
- 2001-08-17 MX MXPA03000838A patent/MXPA03000838A/es active IP Right Grant
- 2001-08-17 EA EA200300278A patent/EA006155B1/ru not_active IP Right Cessation
- 2001-08-17 CZ CZ2003461A patent/CZ2003461A3/cs unknown
- 2001-08-17 DK DK01957788T patent/DK1309586T3/da active
- 2001-08-17 HU HU0302777A patent/HUP0302777A2/hu unknown
- 2001-08-17 AU AU2001279611A patent/AU2001279611B2/en not_active Ceased
- 2001-08-17 AT AT01957788T patent/ATE321040T1/de not_active IP Right Cessation
- 2001-08-17 CA CA002419266A patent/CA2419266A1/fr not_active Abandoned
- 2001-08-17 BR BR0113452-3A patent/BR0113452A/pt not_active IP Right Cessation
- 2001-08-17 PL PL01363309A patent/PL363309A1/xx not_active Application Discontinuation
- 2001-08-17 DE DE60118205T patent/DE60118205T2/de not_active Expired - Fee Related
- 2001-08-17 SK SK321-2003A patent/SK3212003A3/sk unknown
- 2001-08-17 PT PT01957788T patent/PT1309586E/pt unknown
- 2001-08-17 KR KR10-2003-7001687A patent/KR20030022363A/ko not_active Ceased
- 2001-08-17 JP JP2002521450A patent/JP2004506731A/ja not_active Withdrawn
- 2001-08-17 NZ NZ523786A patent/NZ523786A/en unknown
- 2001-08-17 EP EP01957788A patent/EP1309586B1/fr not_active Expired - Lifetime
- 2001-08-17 ES ES01957788T patent/ES2257424T3/es not_active Expired - Lifetime
- 2001-08-17 UA UA2003010504A patent/UA74837C2/uk unknown
- 2001-08-17 IL IL15405101A patent/IL154051A0/xx unknown
2003
- 2003-01-20 IS IS6694A patent/IS6694A/is unknown
- 2003-01-21 ZA ZA200300562A patent/ZA200300562B/en unknown
- 2003-02-03 NO NO20030522A patent/NO20030522L/no not_active Application Discontinuation
- 2003-02-04 US US10/359,052 patent/US6958338B2/en not_active Expired - Fee Related
- 2003-03-06 BG BG107611A patent/BG107611A/bg unknown
2005
- 2005-09-01 US US11/219,544 patent/US7105543B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
MXPA03000838A (es)	2003-06-06
CN1243750C (zh)	2006-03-01
EP1309586A1 (fr)	2003-05-14
JP2004506731A (ja)	2004-03-04
EA200300278A1 (ru)	2003-06-26
AU2001279611B2 (en)	2006-08-10
US7105543B2 (en)	2006-09-12
AR030357A1 (es)	2003-08-20
NZ523786A (en)	2005-07-29
DK1309586T3 (da)	2006-07-10
CZ2003461A3 (cs)	2003-05-14
US20060004022A1 (en)	2006-01-05
PT1309586E (pt)	2006-06-30
BR0113452A (pt)	2003-07-15
EA006155B1 (ru)	2005-10-27
DE60118205T2 (de)	2006-11-02
ZA200300562B (en)	2004-08-23
ATE321040T1 (de)	2006-04-15
US6958338B2 (en)	2005-10-25
CN1447806A (zh)	2003-10-08
IS6694A (is)	2003-01-20
CA2419266A1 (fr)	2002-02-28
PL363309A1 (en)	2004-11-15
HK1059438A1 (en)	2004-07-02
US20030166665A1 (en)	2003-09-04
NO20030522D0 (no)	2003-02-03
HRP20030052A2 (en)	2005-02-28
ES2257424T3 (es)	2006-08-01
SK3212003A3 (en)	2003-07-01
IL154051A0 (en)	2003-07-31
BG107611A (bg)	2003-12-31
HUP0302777A2 (hu)	2003-12-29
NO20030522L (no)	2003-02-03
EP1309586B1 (fr)	2006-03-22
KR20030022363A (ko)	2003-03-15
DE60118205D1 (de)	2006-05-11
WO2002016349A1 (fr)	2002-02-28
AU7961101A (en)	2002-03-04

Publication	Publication Date	Title
EA021440B1 (ru)	2015-06-30	Способ производства фармацевтически активного вещества
UA74837C2 (en)	2006-02-15	4-, 5-, 6- and 7-methylene substituted indole derivatives being useful for the treatment of cns disorders, a pharmaceutical composition and a method for treatment
NO20032636L (no)	2003-06-11	3-indolinderivater som er nyttige i behandlingen av psykiatriske og nevrologiske forstyrrelser
AU2001279611A1 (en)	2002-05-30	4-, 5-, 6- and 7-indole derivatives useful for the treatment of CNS disorders
DE60130691T2 (de)	2008-07-17	Indolderivate zur Behandlung von Erkrankungen des Zentralnervensystems
CA2416212C (fr)	2007-10-30	Derives d'indole utiles dans le traitement de troubles du systeme nerveux central
AU2001273881A1 (en)	2002-03-14	Indole derivatives useful for the treatment of CNS disorders
AU2001273883A1 (en)	2002-01-02	Indole derivatives useful for the treatment of cns disorders
ZA200209997B (en)	2003-12-10	Indole derivatives useful for the treatment of CNS disorders.
IL153234A (en)	2007-12-03	Indole derivatives and pharmaceutical compositions containing them for the treatment of cns disorders