NO326546B1 - Pyridinderivater, fremgangsmate for fremstilling derav samt farmasoytisk preparat omfattende en slik forbindelse - Google Patents

Pyridinderivater, fremgangsmate for fremstilling derav samt farmasoytisk preparat omfattende en slik forbindelse Download PDF

Info

Publication number: NO326546B1
Authority: NO; Norway
Prior art keywords: compound; hydrogen; formula; phenyl; chlorophenyl
Prior art date: 2001-03-26

Application number

NO20034122A

Other languages

English (en)

Norwegian (no)

Other versions

NO20034122D0 (no

NO20034122L (no

Inventor

Peter Gull

Andrew James Culshaw

Allan Hallett

Hong-Yong Kim

Kaspar Zimmermann

Yugang Liu

Max Peter Seiler

Original Assignee

Novartis Ag

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.)

2001-03-26

Filing date

2003-09-16

Publication date

2009-01-05

2001-03-26 Priority claimed from GB0107505A external-priority patent/GB0107505D0/en

2003-09-16 Application filed by Novartis Ag filed Critical Novartis Ag

2003-09-16 Publication of NO20034122D0 publication Critical patent/NO20034122D0/no

2003-09-16 Publication of NO20034122L publication Critical patent/NO20034122L/no

2009-01-05 Publication of NO326546B1 publication Critical patent/NO326546B1/no

Links

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Classifications

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Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Pulmonology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Heart & Thoracic Surgery (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Cardiology (AREA)
Dermatology (AREA)
Physical Education & Sports Medicine (AREA)
Diabetes (AREA)
Immunology (AREA)
Urology & Nephrology (AREA)
Hematology (AREA)
Vascular Medicine (AREA)
Orthopedic Medicine & Surgery (AREA)
Otolaryngology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pyridine Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

NO20034122A 2001-03-26 2003-09-16 Pyridinderivater, fremgangsmate for fremstilling derav samt farmasoytisk preparat omfattende en slik forbindelse NO326546B1 (no)

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GB0107505A GB0107505D0 (en)	2001-03-26	2001-03-26	Organic compounds
US33828101P	2001-12-06	2001-12-06
PCT/EP2002/003332 WO2002076946A2 (en)	2001-03-26	2002-03-25	Fused pyridine derivatives for use as vanilloid receptor antagonists for treating pain.

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US (1)	US7915264B2 (cs)
EP (1)	EP1377576A2 (cs)
JP (1)	JP4205430B2 (cs)
KR (1)	KR20030083755A (cs)
CN (1)	CN1500089A (cs)
BR (1)	BR0208338A (cs)
CA (1)	CA2441599A1 (cs)
CZ (1)	CZ20032561A3 (cs)
HU (1)	HUP0303623A2 (cs)
IL (1)	IL157815A0 (cs)
MX (1)	MXPA03008754A (cs)
NO (1)	NO326546B1 (cs)
PE (1)	PE20021161A1 (cs)
PL (1)	PL363907A1 (cs)
RU (1)	RU2003130221A (cs)
SK (1)	SK11952003A3 (cs)
WO (1)	WO2002076946A2 (cs)

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EP1311478B1 (en)	2000-08-21	2006-06-07	Pacific Corporation	Novel (thio)urea compounds and the pharmaceutical compositions containing the same
JP5001505B2 (ja)	2000-08-21	2012-08-15	株式會社アモーレパシフィック	新規チオウレア誘導体およびこれを含有する薬学的組成物
WO2003062209A2 (en)	2002-01-17	2003-07-31	Neurogen Corporation	Substituted quinazolin-4-ylamine analogues as modulators of capsaicin
EP2033951A3 (en)	2002-02-01	2009-12-23	Euro-Celtique S.A.	2-Piperazine-pyridines useful for treating pain
US6864261B2 (en)	2002-05-02	2005-03-08	Euro-Celtique S.A.	Therapeutic agents useful for treating pain
GB0229808D0 (en) *	2002-12-20	2003-01-29	Glaxo Group Ltd	Novel compositions
ATE450533T1 (de)	2003-02-14	2009-12-15	Glaxo Group Ltd	Carboxamidderivate
ATE556067T1 (de)	2003-05-20	2012-05-15	Ajinomoto Kk	Modulatoren des vanilloid rezeptors
GB0319150D0 (en)	2003-08-14	2003-09-17	Glaxo Group Ltd	Novel compounds
JP2007511496A (ja)	2003-11-14	2007-05-10	メルクシャープエンドドームリミテッド	バニロイド−１受容体（ｖｒ１）の機能を調節する二環式ピリミジン−４−（３ｈ）−オン類並びにその類似体及び誘導体
GB0412769D0 (en) *	2004-06-08	2004-07-07	Novartis Ag	Organic compounds
WO2006019965A2 (en) *	2004-07-16	2006-02-23	Takeda San Diego, Inc.	Dipeptidyl peptidase inhibitors
US7879866B2 (en)	2004-07-19	2011-02-01	Dorte Xenia Gram	Inhibition of the activity of the capsaicin receptor in the treatment of obesity or obesity-related diseases and disorders
DE102004039373A1 (de) *	2004-08-12	2006-02-23	Grünenthal GmbH	Para-Alkyl-substituierte N-(4-Hydroxy-3-methoxy-benzyl)-zimtsäureamide und deren Verwendung zur Herstellung von Arzneimitteln
KR20060087386A (ko)	2005-01-28	2006-08-02	주식회사 대웅제약	신규 벤조이미다졸 유도체 및 이를 함유하는 약제학적조성물
WO2006098554A1 (en) *	2005-03-16	2006-09-21	Amorepacific Corporation	Novel compounds, isomer thereof or pharmaceutically acceptable salts thereof as vanilloid receptor antagonist; and a pharmaceutical composition containing the same
GB0506147D0 (en) *	2005-03-24	2005-05-04	Merck Sharp & Dohme	Therapeutic agents
US20090298856A1 (en) *	2005-05-11	2009-12-03	Rebecca Elizabeth Brown	2,3 Substituted fused bicyclic pyrimidin-4(3H)-ones modulating the function of the vanilliod-1receptor (VR1)
GB0509573D0 (en) *	2005-05-11	2005-06-15	Merck Sharp & Dohme	Therapeutic compounds
BRPI0618417A2 (pt) *	2005-10-19	2012-07-31	Gruenenthal Chemie	novos ligandos de receptores de vanilàide e seu uso para produzir medicamentos
GB0525068D0 (en)	2005-12-08	2006-01-18	Novartis Ag	Organic compounds
KR100761222B1 (ko) *	2006-03-08	2007-10-04	성균관대학교산학협력단	약물의존중독을 예방 및 치료하기 위한 바닐로이드 수용체길항제
GB0614471D0 (en)	2006-07-20	2006-08-30	Syngenta Ltd	Herbicidal Compounds
CN104292229A (zh)	2006-08-23	2015-01-21	神经能质公司	2-苯氧基嘧啶酮类似物
US20080207659A1 (en)	2007-02-15	2008-08-28	Asit Kumar Chakraborti	Inhibitors of phosphodiesterase type 4
CL2008001112A1 (es) *	2007-04-20	2008-12-19	Novartis Ag	Usos de compuestos derivados de pirido[2,3-d]pirimidin-4-ona para tratar comezon o un trastorno relacionado con comezon; combinacion de los compuestos con otro farmaco; y uso de la combinacion para tratar la comezon o un trastorno relacionado con comezon.
EP2178562B1 (en) *	2007-07-18	2017-08-23	Novartis AG	Synergistic combinations of vr-1 antagonists and cox-2 inhibitors
US8349846B2 (en) *	2008-01-11	2013-01-08	Glenmark Pharmaceuticals, S.A.	Fused pyrimidine derivatives as TRPV3 modulators
WO2009121036A2 (en) *	2008-03-27	2009-10-01	Neurogen Corporation	Substituted aryl pyrimidinone derivatives
CN101983197B (zh)	2008-04-18	2015-04-22	大熊制药株式会社	新型苯并噁嗪苯并咪唑衍生物、含有该衍生物的药物组合物及其用途
US8349852B2 (en)	2009-01-13	2013-01-08	Novartis Ag	Quinazolinone derivatives useful as vanilloid antagonists
WO2011092293A2 (en)	2010-02-01	2011-08-04	Novartis Ag	Cyclohexyl amide derivatives as crf receptor antagonists
AR080055A1 (es)	2010-02-01	2012-03-07	Novartis Ag	Derivados de pirazolo-[5,1-b]-oxazol como antagonistas de los receptores de crf -1
US8835444B2 (en)	2010-02-02	2014-09-16	Novartis Ag	Cyclohexyl amide derivatives as CRF receptor antagonists
KR101293384B1 (ko)	2010-10-13	2013-08-05	주식회사 대웅제약	신규 피리딜 벤조옥사진 유도체, 이를 포함하는 약학 조성물 및 이의 용도
AR086554A1 (es)	2011-05-27	2014-01-08	Novartis Ag	Derivados de la piperidina 3-espirociclica como agonistas de receptores de la ghrelina
EP2852591A1 (en)	2012-05-03	2015-04-01	Novartis AG	L-malate salt of 2, 7 - diaza - spiro [4.5]dec- 7 - yle derivatives and crystalline forms thereof as ghrelin receptor agonists
ES2991706T3 (es)	2015-12-23	2024-12-04	Commw Scient Ind Res Org	Compuestos de enamina para protección contra radiación UV
CN111393380A (zh) *	2018-07-09	2020-07-10	湖南博隽生物医药有限公司	一种用于治疗慢性炎性痛的辣椒素受体拮抗剂
DE102022104759A1 (de)	2022-02-28	2023-08-31	SCi Kontor GmbH	Co-Kristall-Screening Verfahren, insbesondere zur Herstellung von Co-Kristallen
CN114605408B (zh) *	2022-03-30	2023-06-16	沈阳药科大学	5-羟基-1,3-二取代苯基吡啶并[2,3-d]嘧啶类化合物及其制法和应用

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2749344A (en) *	1953-01-02	1956-06-05	Burroughs Wellcome Co	Pyrimidine compounds
US5958930A (en)	1991-04-08	1999-09-28	Duquesne University Of The Holy Ghost	Pyrrolo pyrimidine and furo pyrimidine derivatives
US5620978A (en)	1994-01-03	1997-04-15	State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon, Eugene Oregon	8-aza, 6-aza and 6,8-diaza-1,4-dihydroquinoxaline-2,3-diones and the use thereof as antagonists for the glycine/NMDA receptor
FR2750862B1 (fr)	1996-07-12	1998-10-16	Dupin Jean Pierre	Utilisation d'heterocycles diazotes fusionnes avec un systeme aromatique ou heteroaromatique pour le traitement des maladies thrombo-emboliques

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NO20034122D0 (no)	2003-09-16
EP1377576A2 (en)	2004-01-07
SK11952003A3 (sk)	2004-03-02
KR20030083755A (ko)	2003-10-30
IL157815A0 (en)	2004-03-28
MXPA03008754A (es)	2004-02-18
US20040138454A1 (en)	2004-07-15
JP2004528312A (ja)	2004-09-16
US7915264B2 (en)	2011-03-29
WO2002076946A3 (en)	2002-12-27
CZ20032561A3 (cs)	2003-12-17
CN1500089A (zh)	2004-05-26
PE20021161A1 (es)	2003-02-21
JP4205430B2 (ja)	2009-01-07
PL363907A1 (en)	2004-11-29
NO20034122L (no)	2003-09-16
RU2003130221A (ru)	2005-04-10
HUP0303623A2 (hu)	2004-03-01
WO2002076946A2 (en)	2002-10-03
CA2441599A1 (en)	2002-10-03
BR0208338A (pt)	2004-03-09

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Publication	Publication Date	Title
NO326546B1 (no)	2009-01-05	Pyridinderivater, fremgangsmate for fremstilling derav samt farmasoytisk preparat omfattende en slik forbindelse
AU2017282903B2 (en)	2021-03-25	Crystals of aniline pyrimidine compound serving as EGFR inhibitor
EP3197867B1 (en)	2018-11-14	Novel 4-methoxy pyrrole derivatives or salts thereof and pharmaceutical composition comprising the same
EP1910370B1 (en)	2015-04-22	A pyridin quinolin substituted pyrrolo [1,2-b] pyrazole monohydrate as tgf-beta inhibitor
RU2396261C2 (ru)	2010-08-10	Производные хиназолинона, полезные в качестве ванилоидных антагонистов
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JPH09509188A (ja)	1997-09-16	新規なピリミジン誘導体およびその製造方法
ZA200005881B (en)	2001-08-23	Amide derivatives and nociceptin antagonists.
EP0534706A1 (en)	1993-03-31	Quinazolinones and pyridopyrimidinones useful as angiotensin II antagonists
EP1339706B1 (en)	2006-04-19	N-type calcium channel antagonists for the treatment of pain
CZ20003974A3 (en)	2001-05-16	Anhydrate and monohydrate of N-(3-ethinylphenylamino)-6,7-bis(2-methoxyethoxy)-4-quinazolinamine mesylate
JP2008534597A (ja)	2008-08-28	ＰＫＣ−θのインヒビターとして有用なピリジン誘導体
EP0169537A2 (en)	1986-01-29	2-Phenylalkyl-3-aminoalkyl-4(3H)-quinazolinones, processes for preparing them, pharmaceutical compositions and use
EP1309569B1 (en)	2010-10-06	N-aryl-{4-[7-(alkoxy)quinazolin-4-yl]piperazinyl}carboxamide derivatives as PDGFRs inhibitors
WO2002016360A2 (en)	2002-02-28	Nitrogenous heterocyclic compounds
AU2022395869A1 (en)	2024-06-13	Mono-p-toluenesulfonate of axl kinase inhibitor and crystal form thereof
WO2017071607A1 (zh)	2017-05-04	4H-吡唑并[1,5-α]苯并咪唑类化合物晶型及其制备方法和中间体
JP2003509494A (ja)	2003-03-11	ムスカリン拮抗薬
NO843292L (no)	1985-02-21	Fremgangsmaate for fremstilling av nye kinolon-derivater
US20040053965A1 (en)	2004-03-18	N-type calcium channel antagonists for the treatment of pain
US20040259881A1 (en)	2004-12-23	Nitrogenous heterocyclic compounds
AU2002302469A1 (en)	2002-10-08	Fused pyridine derivatives for use as vanilloid receptor antagonists for treating pain.
ZA200306636B (en)	2004-08-19	Fused pyridine derivatives for use as vanilloid receptor antagonists for treating pain.