UA62015C2 - Benzoizoxazol derivatives, a pharmaceutical composition (variants) based thereon (variants) and a method for treatment (variants) - Google Patents

Benzoizoxazol derivatives, a pharmaceutical composition (variants) based thereon (variants) and a method for treatment (variants) Download PDF

Info

Publication number: UA62015C2
Authority: UA; Ukraine
Prior art keywords: disorder; treatment; mammal; disease; condition
Prior art date: 1998-12-28

Application number

UA2001064492A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Pfizer Prod Inc

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.)

1998-12-28

Filing date

1999-03-11

Publication date

2003-12-15

1999-03-11 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2003-12-15 Publication of UA62015C2 publication Critical patent/UA62015C2/uk

Links

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Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Epidemiology (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Psychology (AREA)
Diabetes (AREA)
Hospice & Palliative Care (AREA)
Obesity (AREA)
Addiction (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Urology & Nephrology (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Gynecology & Obstetrics (AREA)
Child & Adolescent Psychology (AREA)
Dermatology (AREA)
Hematology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

UA2001064492A 1998-12-28 1999-03-11 Benzoizoxazol derivatives, a pharmaceutical composition (variants) based thereon (variants) and a method for treatment (variants) UA62015C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US11395798P	1998-12-28	1998-12-28
PCT/IB1999/001772 WO2000039128A1 (en)	1998-12-28	1999-11-03	5ht1 antagonists for antidepressant therapy

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UA2001064492A UA62015C2 (en)	1998-12-28	1999-03-11	Benzoizoxazol derivatives, a pharmaceutical composition (variants) based thereon (variants) and a method for treatment (variants)

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US (1)	US6525196B1 (es)
EP (1)	EP1140931B1 (es)
JP (1)	JP2002533463A (es)
KR (1)	KR100417506B1 (es)
CN (1)	CN1332740A (es)
AP (1)	AP2001002188A0 (es)
AR (1)	AR024840A1 (es)
AT (1)	ATE260278T1 (es)
AU (1)	AU761711B2 (es)
BG (1)	BG105710A (es)
BR (1)	BR9916807A (es)
CA (1)	CA2356985C (es)
CO (1)	CO5150179A1 (es)
CR (1)	CR6398A (es)
CZ (1)	CZ291163B6 (es)
DE (1)	DE69915113T2 (es)
DK (1)	DK1140931T3 (es)
DZ (1)	DZ2933A1 (es)
EA (1)	EA003099B1 (es)
EE (1)	EE04439B1 (es)
ES (1)	ES2214892T3 (es)
GE (1)	GEP20043227B (es)
GT (1)	GT199900224A (es)
HR (1)	HRP20010488A2 (es)
HU (1)	HUP0104852A3 (es)
ID (1)	ID30117A (es)
IL (1)	IL143385A0 (es)
IS (1)	IS5951A (es)
MA (1)	MA26706A1 (es)
NO (1)	NO20013215L (es)
NZ (1)	NZ511964A (es)
OA (1)	OA11742A (es)
PA (1)	PA8486701A1 (es)
PE (1)	PE20001234A1 (es)
PT (1)	PT1140931E (es)
SK (1)	SK9002001A3 (es)
TN (1)	TNSN99218A1 (es)
TR (1)	TR200101979T2 (es)
TW (1)	TW523514B (es)
UA (1)	UA62015C2 (es)
WO (1)	WO2000039128A1 (es)
YU (1)	YU44301A (es)
ZA (1)	ZA200105041B (es)

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WO2003065970A2 (en) *	2001-02-20	2003-08-14	Royal College Of Surgeons Ie	Treatment of fibromyalgia and related fatigue syndromes using pindolol
GB0203778D0 (en) *	2002-02-18	2002-04-03	Glaxo Group Ltd	Compounds
AP2005003390A0 (en) *	2003-03-12	2005-09-30	Pfizer Prod Inc	Pyridyloxymethyl and benzisoxazole azabicyclic derivatives.
GB0316915D0 (en) *	2003-07-18	2003-08-20	Glaxo Group Ltd	Compounds
WO2005082370A1 (en) *	2004-01-29	2005-09-09	Pfizer Products Inc.	Combinations of an atypical antipsychotic and an aminomethylpyridyloxymethyl/benzisoxazole azabicyclic derivatives for treating cns disorders
AR048112A1 (es) *	2004-03-25	2006-03-29	Solvay Pharm Bv	Derivados de 1-(2h-1-benzopiran-2-on-8-il)-piperazina para el tratamiento de dolor
AR049478A1 (es)	2004-03-25	2006-08-09	Solvay Pharm Bv	Un procedimiento para la preparacion de 3-amino-8-(1-piperazinil)-2h-1-benzopiran-2-ona. sales e hidratos y composiciones farmaceuticas.
BRPI0515143A (pt) *	2004-09-10	2008-07-08	Pfizer Prod Inc	usos de derivados azabicìclicos de piridiloximetila e benzisoxazol para a preparação de uma composição farmacêutica para o tratamento dos distúrbios de humor
JP2008512441A (ja) *	2004-09-10	2008-04-24	ファイザー・プロダクツ・インク	ピリジルオキシメチル、及びベンズイソオキサゾール・アザビシクロ誘導体を使用する、認知障害の治療方法
DE102005026194A1 (de) *	2005-06-06	2006-12-07	Grünenthal GmbH	Substituierte N-Benzo[d]isoxazol-3-yl-amin-Derivate und deren Verwendung zur Herstellung von Arzneimitteln
WO2008019431A1 (en) *	2006-08-14	2008-02-21	Brc Operations Pty Limited	Method and compositions for simultaneously regulating memory and mood
WO2014078568A1 (en)	2012-11-14	2014-05-22	The Johns Hopkins University	Methods and compositions for treating schizophrenia
WO2020183011A1 (en)	2019-03-14	2020-09-17	Institut Curie	Htr1d inhibitors and uses thereof in the treatment of cancer
WO2021127391A1 (en) *	2019-12-20	2021-06-24	The Jackson Laboratory	Molecular targets for addiction

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5157034A (en) *	1991-02-27	1992-10-20	Pfizer Inc.	Neuroleptic perhydro-1H-pyrido[1,2-a]pyrazines
GB9410512D0 (en) *	1994-05-25	1994-07-13	Smithkline Beecham Plc	Novel treatment
US5756496A (en) *	1994-05-28	1998-05-26	Smithkline Beecham P.L.C.	Amide derivatives having 5HT1D-antagonist activity
IL132409A0 (en) *	1997-04-18	2001-03-19	Smithkline Beecham Plc	Indole derivatives having combined 5ht1a 5ht1b and 5ht1d receptor antagonist activity
IT1293807B1 (it) *	1997-08-01	1999-03-10	Recordati Chem Pharm	Derivati 1- (n-fenilaminoalchil) piperazinici sostituiti alla posizione 2 dell'anello fenilico
PA8469101A1 (es) *	1998-04-09	2000-09-29	Pfizer Prod Inc	Ligandos azabiciclicos de receptores 5ht1

1999
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- 1999-11-03 WO PCT/IB1999/001772 patent/WO2000039128A1/en not_active Ceased
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- 1999-11-10 DZ DZ990233A patent/DZ2933A1/xx active
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Also Published As

Publication number	Publication date
ATE260278T1 (de)	2004-03-15
GT199900224A (es)	2001-06-15
HRP20010488A2 (en)	2002-08-31
YU44301A (sh)	2004-07-15
DE69915113T2 (de)	2004-08-26
OA11742A (en)	2005-05-13
PT1140931E (pt)	2004-05-31
DE69915113D1 (de)	2004-04-01
EE04439B1 (et)	2005-02-15
IL143385A0 (en)	2002-04-21
BG105710A (en)	2002-02-28
TNSN99218A1 (fr)	2005-11-10
GEP20043227B (en)	2004-04-26
BR9916807A (pt)	2001-10-23
HUP0104852A3 (en)	2002-12-28
NO20013215L (no)	2001-08-27
CR6398A (es)	2004-03-24
PE20001234A1 (es)	2000-11-07
CZ20012386A3 (cs)	2002-02-13
HUP0104852A2 (hu)	2002-05-29
CZ291163B6 (cs)	2003-01-15
AU6361499A (en)	2000-07-31
US6525196B1 (en)	2003-02-25
PA8486701A1 (es)	2000-09-29
EA200100517A1 (ru)	2001-12-24
WO2000039128A1 (en)	2000-07-06
KR100417506B1 (ko)	2004-02-05
SK9002001A3 (en)	2002-04-04
CO5150179A1 (es)	2002-04-29
AP2001002188A0 (en)	2001-06-30
CA2356985C (en)	2006-08-08
EP1140931A1 (en)	2001-10-10
NZ511964A (en)	2003-08-29
AU761711B2 (en)	2003-06-05
EA003099B1 (ru)	2002-12-26
DK1140931T3 (da)	2004-04-19
CN1332740A (zh)	2002-01-23
TR200101979T2 (tr)	2001-12-21
NO20013215D0 (no)	2001-06-27
EP1140931B1 (en)	2004-02-25
ES2214892T3 (es)	2004-09-16
IS5951A (is)	2001-05-22
KR20010092455A (ko)	2001-10-25
CA2356985A1 (en)	2000-07-06
ZA200105041B (en)	2002-06-20
DZ2933A1 (fr)	2004-03-15
TW523514B (en)	2003-03-11
AR024840A1 (es)	2002-10-30
ID30117A (id)	2001-11-08
MA26706A1 (fr)	2004-12-20
JP2002533463A (ja)	2002-10-08
EE200100346A (et)	2002-12-16

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