NO329380B1 - Benzoksazin-derivater, fremgangsmate for fremstilling av slike, farmasoytiske preparater omfattende slike samt anvendelse av slike for fremstilling av medikamenter for behandling eller forebygging av sykdom - Google Patents

Benzoksazin-derivater, fremgangsmate for fremstilling av slike, farmasoytiske preparater omfattende slike samt anvendelse av slike for fremstilling av medikamenter for behandling eller forebygging av sykdom Download PDF

Info

Publication number: NO329380B1
Authority: NO; Norway
Prior art keywords: dihydro; benzo; compound according; oxazine; piperazin
Prior art date: 2002-05-13

Application number

NO20044665A

Other languages

English (en)

Norwegian (no)

Other versions

NO20044665L (no

Inventor

Jacob Berger

Robin Douglas Clark

Shu Hai Zhao

Original Assignee

Hoffmann La Roche

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.)

2002-05-13

Filing date

2004-10-28

Publication date

2010-10-04

2004-10-28 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

2004-12-03 Publication of NO20044665L publication Critical patent/NO20044665L/no

2010-10-04 Publication of NO329380B1 publication Critical patent/NO329380B1/no

Links

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230000000699 topical effect Effects 0.000 description 1
230000037317 transdermal delivery Effects 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
238000011269 treatment regimen Methods 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
229940029284 trichlorofluoromethane Drugs 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
229960000281 trometamol Drugs 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000011345 viscous material Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
- 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
- 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
- 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
- A61P25/22—Anxiolytics
- 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
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/02—Seven-membered rings
- C07D267/08—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D267/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D267/14—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

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

NO20044665A 2002-05-13 2004-10-28 Benzoksazin-derivater, fremgangsmate for fremstilling av slike, farmasoytiske preparater omfattende slike samt anvendelse av slike for fremstilling av medikamenter for behandling eller forebygging av sykdom NO329380B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US37800302P	2002-05-13	2002-05-13
PCT/EP2003/004671 WO2003095434A1 (en)	2002-05-13	2003-05-05	Benzoxazine derivatives as 5-ht6 modulators and uses thereof

Publications (2)

Publication Number	Publication Date
NO20044665L NO20044665L (no)	2004-12-03
NO329380B1 true NO329380B1 (no)	2010-10-04

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ID=29420358

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20044665A NO329380B1 (no)	2002-05-13	2004-10-28	Benzoksazin-derivater, fremgangsmate for fremstilling av slike, farmasoytiske preparater omfattende slike samt anvendelse av slike for fremstilling av medikamenter for behandling eller forebygging av sykdom

Country Status (37)

Country	Link
US (4)	US6867204B2 (xx)
EP (1)	EP1506179B1 (xx)
JP (1)	JP4307377B2 (xx)
KR (1)	KR100636475B1 (xx)
CN (1)	CN100429206C (xx)
AR (1)	AR039988A1 (xx)
AT (1)	ATE316523T1 (xx)
AU (1)	AU2003233231B2 (xx)
BR (1)	BRPI0310032B8 (xx)
CA (1)	CA2485136C (xx)
DE (1)	DE60303376T2 (xx)
DK (1)	DK1506179T3 (xx)
EA (1)	EA009982B1 (xx)
EC (1)	ECSP045420A (xx)
EG (1)	EG25683A (xx)
ES (1)	ES2256744T3 (xx)
GT (1)	GT200300108A (xx)
HK (1)	HK1080846A1 (xx)
HR (1)	HRP20041030B1 (xx)
IL (1)	IL164928A0 (xx)
JO (1)	JO2413B1 (xx)
MA (1)	MA27118A1 (xx)
MX (1)	MXPA04011254A (xx)
MY (1)	MY139612A (xx)
NO (1)	NO329380B1 (xx)
NZ (1)	NZ536230A (xx)
PA (1)	PA8573501A1 (xx)
PE (1)	PE20040757A1 (xx)
PL (1)	PL211057B1 (xx)
PT (1)	PT1506179E (xx)
RS (1)	RS51042B (xx)
TN (1)	TNSN04225A1 (xx)
TW (1)	TWI258479B (xx)
UA (1)	UA76877C2 (xx)
UY (1)	UY27803A1 (xx)
WO (1)	WO2003095434A1 (xx)
ZA (1)	ZA200408783B (xx)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK1408976T5 (da)	2001-07-20	2011-01-10	Psychogenics Inc	Behandling af ADHD (Attention deficit hyperactivity disorder)
AR039127A1 (es)	2002-03-27	2005-02-09	Glaxo Group Ltd	Compuesto de quinolina, procedimiento para su preparacion, composicion farmaceutica que lo comprende y uso del mismo para la fabricacion de un medicamento
CA2485136C (en) *	2002-05-13	2011-12-20	F. Hoffmann-La Roche Ag	Benzoxazine derivatives as 5-ht6 modulators and uses thereof
WO2004041792A1 (en) *	2002-11-08	2004-05-21	F. Hoffmann-La Roche Ag	Substituted benzoxazinones and uses thereof
JP4198733B2 (ja)	2003-07-22	2008-12-17	アリーナファーマシューティカルズ，インコーポレイテッド	関連性障害の予防および処置に有用な、５−ｈｔ２ａセロトニンレセプターのモジュレーターとしてのジアリールおよびアリールへテロアリールウレア誘導体
NZ547120A (en) *	2003-12-09	2009-02-28	Hoffmann La Roche	Benzoxazine derivatives having 2,2-dialkyl substituents at the 2-position of the benzoxazine ring system
RU2006129464A (ru) *	2004-01-16	2008-02-27	Ф.Хоффманн-Ля Рош Аг (Ch)	Производные 1-бензил-5-пиперазин-1-ил-3, 4-дигидро-1н-хиназолин-2-она и соответствующие производные 1н-бензо (1, 2, 6) тиадиазин-2, 2-диоксида и 1, 4-дигидробензо (1, 3)оксазин-2-она в качестве модуляторов рецептора 5-гидрокситриптамина (5нт) для лечения заболевания центральной нервной системы
RU2372344C2 (ru) *	2004-05-05	2009-11-10	Ф. Хоффманн-Ля Рош Аг	Арилсульфонилбензодиоксаны, применяемые для модуляции 5-нт6 рецептора, 5-нт2a рецептора или и того, и другого
US7378415B2 (en) *	2004-09-30	2008-05-27	Roche Palo Alto Llc	Benzoxazine and quinoxaline derivatives and uses thereof
DE602005022896D1 (de) *	2004-09-30	2010-09-23	Hoffmann La Roche	Benzoxazin- und chinoxalinderivate und anwendungen
US7713954B2 (en) *	2004-09-30	2010-05-11	Roche Palo Alto Llc	Compositions and methods for treating cognitive disorders
EP1799306B1 (en) *	2004-09-30	2011-02-23	F. Hoffmann-La Roche AG	Compositions and methods for treating cognitive disorders
EP2254564A1 (en)	2007-12-12	2010-12-01	Glaxo Group Limited	Combinations comprising 3-phenylsulfonyl-8-piperazinyl-1yl-quinoline
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
WO2010062321A1 (en)	2008-10-28	2010-06-03	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
AR078770A1 (es) *	2009-10-27	2011-11-30	Elara Pharmaceuticals Gmbh	Derivados de dihidrobenzo oxacinas y tiazinas, composiciones farmaceuticas que los contienen y uso de los mismos para el tratamiento de enfermedades inflamatorias e hiperproliferativas.
KR101293384B1 (ko) *	2010-10-13	2013-08-05	주식회사 대웅제약	신규 피리딜 벤조옥사진 유도체, 이를 포함하는 약학 조성물 및 이의 용도
US9403800B2 (en) *	2012-01-24	2016-08-02	Chemregen, Inc.	Compounds for inhibition of cancer cell proliferation
JP6510539B2 (ja)	2014-01-09	2019-05-08	ザジェイ．デヴィッドグラッドストーンインスティテューツ，アテスタメンタリートラストエスタブリッシュドアンダーザウィルオブジェイ．デヴィッドグラッドストーン	置換ベンゾオキサジン及び関連化合物
EP3307260A4 (en)	2015-06-12	2019-02-13	Axovant Sciences GmbH	DIARYL AND ARYLHETEROARYL UREA DERIVATIVES FOR PROPHYLAXIS AND TREATMENT OF SLEEP BEHAVIORAL DISORDERS IN THE REM PHASE
US10034859B2 (en)	2015-07-15	2018-07-31	Axovant Sciences Gmbh	Diaryl and arylheteroaryl urea derivatives as modulators of the 5-HT2A serotonin receptor useful for the prophylaxis and treatment of hallucinations associated with a neurodegenerative disease

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN1029479C (zh) *	1989-11-08	1995-08-09	山之内制药株式会社	新型苯并噁嗪衍生物的制备方法
US5492914A (en) *	1994-07-28	1996-02-20	Syntex (U.S.A.) Inc.	2-(1-azabicyclo[2.2.2]oct-3 s-yl)-6-hydroxy-2,4,5,6-tetrahydro-1H-benz[DE]is[2.2.2]oct-3's-yl)-6-hydroxy-2,3,3a,4,5,6-hexahydro-1h-benz [DE]isoquinolin-1-one and individual stereoisomers thereof
GB9507203D0 (en)	1995-04-07	1995-05-31	Smithkline Beecham Plc	Novel compounds
DZ2376A1 (fr) *	1996-12-19	2002-12-28	Smithkline Beecham Plc	Dérivés de sulfonamides nouveaux procédé pour leurpréparation et compositions pharmaceutiques les c ontenant.
NZ500252A (en)	1997-04-18	2001-07-27	Smithkline Beecham P	6-(4-Methyl-piperazin-1-yl)-1H-indole derivatives useful as 5HT1A, 5HT1B and 5HT1D receptor antagonists
ES2244082T3 (es)	1997-07-11	2005-12-01	Smithkline Beecham Plc	Derivados de sulfonamida que son antagonistas del receptor 5-ht6 y procedimiento para su preparacion.
AU736596B2 (en) *	1997-07-25	2001-08-02	H. Lundbeck A/S	Indole and 2,3-dihydroindole derivatives, their preparation and use
GB9801392D0 (en)	1998-01-22	1998-03-18	Smithkline Beecham Plc	Novel compounds
WO1999067237A1 (en) *	1998-06-19	1999-12-29	H. Lundbeck A/S	4,5,6 and 7-indole and indoline derivatives, their preparation and use
GB9818916D0 (en)	1998-08-28	1998-10-21	Smithkline Beecham Plc	Use
US6380235B1 (en)	1999-05-04	2002-04-30	American Home Products Corporation	Benzimidazolones and analogues
RU2246494C2 (ru) *	1999-08-23	2005-02-20	Солвей Фармасьютикалс Б.В.	Новые фенилпиперазины
US6566372B1 (en)	1999-08-27	2003-05-20	Ligand Pharmaceuticals Incorporated	Bicyclic androgen and progesterone receptor modulator compounds and methods
WO2001057003A1 (en)	2000-02-01	2001-08-09	Cor Therapeutics, Inc.	3,4-DIHYDRO-2H-BENZO[1,4]OXAZINE INHIBITORS OF FACTOR Xa
CA2485136C (en) *	2002-05-13	2011-12-20	F. Hoffmann-La Roche Ag	Benzoxazine derivatives as 5-ht6 modulators and uses thereof

2003
- 2003-05-05 CA CA2485136A patent/CA2485136C/en not_active Expired - Lifetime
- 2003-05-05 MX MXPA04011254A patent/MXPA04011254A/es active IP Right Grant
- 2003-05-05 JP JP2004503451A patent/JP4307377B2/ja not_active Expired - Lifetime
- 2003-05-05 WO PCT/EP2003/004671 patent/WO2003095434A1/en active IP Right Grant
- 2003-05-05 NZ NZ536230A patent/NZ536230A/en not_active IP Right Cessation
- 2003-05-05 ES ES03727430T patent/ES2256744T3/es not_active Expired - Lifetime
- 2003-05-05 DE DE60303376T patent/DE60303376T2/de not_active Expired - Lifetime
- 2003-05-05 AU AU2003233231A patent/AU2003233231B2/en not_active Expired
- 2003-05-05 UA UA20041210144A patent/UA76877C2/uk unknown
- 2003-05-05 AT AT03727430T patent/ATE316523T1/de active
- 2003-05-05 RS YUP-970/04A patent/RS51042B/sr unknown
- 2003-05-05 EP EP03727430A patent/EP1506179B1/en not_active Expired - Lifetime
- 2003-05-05 PL PL374019A patent/PL211057B1/pl unknown
- 2003-05-05 KR KR1020047018299A patent/KR100636475B1/ko active IP Right Grant
- 2003-05-05 PT PT03727430T patent/PT1506179E/pt unknown
- 2003-05-05 EA EA200401455A patent/EA009982B1/ru not_active IP Right Cessation
- 2003-05-05 DK DK03727430T patent/DK1506179T3/da active
- 2003-05-05 BR BRPI0310032A patent/BRPI0310032B8/pt not_active IP Right Cessation
- 2003-05-05 CN CNB038109972A patent/CN100429206C/zh not_active Expired - Lifetime
- 2003-05-08 TW TW092112575A patent/TWI258479B/zh not_active IP Right Cessation
- 2003-05-08 JO JO200352A patent/JO2413B1/en active
- 2003-05-09 GT GT200300108A patent/GT200300108A/es unknown
- 2003-05-09 US US10/435,732 patent/US6867204B2/en not_active Expired - Lifetime
- 2003-05-09 PA PA20038573501A patent/PA8573501A1/es unknown
- 2003-05-09 PE PE2003000452A patent/PE20040757A1/es active IP Right Grant
- 2003-05-09 AR ARP030101624A patent/AR039988A1/es active IP Right Grant
- 2003-05-10 EG EG2003050432A patent/EG25683A/xx active
- 2003-05-12 MY MYPI20031765A patent/MY139612A/en unknown
- 2003-05-12 UY UY27803A patent/UY27803A1/es not_active IP Right Cessation
2004
- 2004-10-28 IL IL16492804A patent/IL164928A0/xx unknown
- 2004-10-28 NO NO20044665A patent/NO329380B1/no not_active IP Right Cessation
- 2004-10-29 ZA ZA2004/08783A patent/ZA200408783B/en unknown
- 2004-11-03 HR HRP20041030AA patent/HRP20041030B1/hr not_active IP Right Cessation
- 2004-11-10 EC EC2004005420A patent/ECSP045420A/es unknown
- 2004-11-11 TN TNP2004000225A patent/TNSN04225A1/fr unknown
- 2004-11-12 MA MA27944A patent/MA27118A1/fr unknown
2005
- 2005-01-31 US US11/047,284 patent/US20050130962A1/en not_active Abandoned
2006
- 2006-01-18 HK HK06100802.2A patent/HK1080846A1/xx not_active IP Right Cessation
2009
- 2009-09-04 US US12/584,373 patent/US8377931B2/en not_active Expired - Lifetime
2012
- 2012-12-13 US US13/713,484 patent/US20130123251A1/en not_active Abandoned

Also Published As

Publication number	Publication date
MY139612A (en)	2009-10-30
NO20044665L (no)	2004-12-03
RS97004A (xx)	2006-10-27
MXPA04011254A (es)	2005-01-25
RS51042B (sr)	2010-10-31
EG25683A (en)	2012-05-16
JO2413B1 (en)	2007-11-11
CN1653054A (zh)	2005-08-10
WO2003095434A1 (en)	2003-11-20
ECSP045420A (es)	2005-01-03
EP1506179A1 (en)	2005-02-16
PL211057B1 (pl)	2012-04-30
UY27803A1 (es)	2003-11-28
JP2005530774A (ja)	2005-10-13
TNSN04225A1 (fr)	2007-03-12
US20090325950A1 (en)	2009-12-31
AU2003233231A1 (en)	2003-11-11
KR100636475B1 (ko)	2006-10-18
US20030232825A1 (en)	2003-12-18
CN100429206C (zh)	2008-10-29
ATE316523T1 (de)	2006-02-15
DE60303376T2 (de)	2006-11-16
MA27118A1 (fr)	2004-12-20
BR0310032A (pt)	2005-02-15
AR039988A1 (es)	2005-03-09
US20050130962A1 (en)	2005-06-16
HK1080846A1 (en)	2006-05-04
PE20040757A1 (es)	2004-11-06
US20130123251A1 (en)	2013-05-16
EA009982B1 (ru)	2008-04-28
GT200300108A (es)	2004-03-15
BRPI0310032B8 (pt)	2021-05-25
PA8573501A1 (es)	2003-12-10
JP4307377B2 (ja)	2009-08-05
HRP20041030B1 (hr)	2013-03-31
HRP20041030A2 (en)	2005-06-30
IL164928A0 (en)	2005-12-18
EA200401455A1 (ru)	2005-06-30
UA76877C2 (uk)	2006-09-15
NZ536230A (en)	2007-05-31
AU2003233231B2 (en)	2009-02-26
TWI258479B (en)	2006-07-21
BRPI0310032B1 (pt)	2019-01-08
DK1506179T3 (da)	2006-06-06
KR20040106538A (ko)	2004-12-17
ES2256744T3 (es)	2006-07-16
PT1506179E (pt)	2006-06-30
US8377931B2 (en)	2013-02-19
CA2485136C (en)	2011-12-20
CA2485136A1 (en)	2003-11-20
EP1506179B1 (en)	2006-01-25
TW200400188A (en)	2004-01-01
US6867204B2 (en)	2005-03-15
ZA200408783B (en)	2005-12-28
PL374019A1 (en)	2005-09-19
DE60303376D1 (de)	2006-04-13

Publication	Publication Date	Title
US8377931B2 (en)	2013-02-19	Benzoxazine derivatives and uses thereof
KR100683361B1 (ko)	2007-02-15	치환된 벤즈옥사진온 및 그의 용도
JP4527730B2 (ja)	2010-08-18	ベンゾオキサジン誘導体及びその使用
ES2305742T3 (es)	2008-11-01	Derivados de quinolinon/benzoxazinona y uso de los mismos.
ES2302174T3 (es)	2008-07-01	Derivados 1-bencil-5-piperacin-1-il-3,4-dihidro-1h-quinazolin-2-ona y derivados respectivos de 1h-benzo(1,2,6)tiadiacin-2,2-dioxido y 1,4-dihidro-benzo(d)(1,3)oxacin-2-ona como moduladores del receptor 5-hidroxitriptamina(5-ht) para tratamiento enfermed. sistema nervioso central.
ES2348467T3 (es)	2010-12-07	Derivados y usos de la benzoxazina y la quinoxalina.
KR100875041B1 (ko)	2008-12-19	벤즈옥사진 및 퀴녹살린 유도체 및 용도
MXPA06005840A (en)	2006-10-17	Benzoxazine derivatives and uses thereof

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