BG104107A - 4-АМИНОПИРОЛ/3,2-d/ ПИРИМИДИНИ КАТО РЕЦЕПТОРНИ АНТАГОНИСТИ НА НЕВРОПЕПТИД Y - Google Patents

4-АМИНОПИРОЛ/3,2-d/ ПИРИМИДИНИ КАТО РЕЦЕПТОРНИ АНТАГОНИСТИ НА НЕВРОПЕПТИД Y Download PDF

Info

Publication number: BG104107A
Authority: BG; Bulgaria
Prior art keywords: hydrogen; methyl; mean; alkyl; phenyl
Prior art date: 1997-08-05

Application number

BG104107A

Other languages

Bulgarian (bg)

English (en)

Inventor

Robert DOW

Marlys Hammond

Original Assignee

Pfizer Products 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.)

1997-08-05

Filing date

2000-01-26

Publication date

2000-08-31

2000-01-26 Application filed by Pfizer Products Inc. filed Critical Pfizer Products Inc.

2000-08-31 Publication of BG104107A publication Critical patent/BG104107A/bg

Links

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102400000064 Neuropeptide Y Human genes 0.000 claims abstract description 12
URPYMXQQVHTUDU-OFGSCBOVSA-N nucleopeptide y Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 URPYMXQQVHTUDU-OFGSCBOVSA-N 0.000 claims abstract description 9
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UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Pulmonology (AREA)
Diabetes (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Endocrinology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Biomedical Technology (AREA)
Child & Adolescent Psychology (AREA)
Hematology (AREA)
Obesity (AREA)
Urology & Nephrology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

BG104107A 1997-08-05 2000-01-26 4-АМИНОПИРОЛ/3,2-d/ ПИРИМИДИНИ КАТО РЕЦЕПТОРНИ АНТАГОНИСТИ НА НЕВРОПЕПТИД Y BG104107A (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US5473497P	1997-08-05	1997-08-05
PCT/IB1998/001053 WO1999007703A1 (fr)	1997-08-05	1998-07-10	4-AMINOPYRROLE(3,2-d)PYRIMIDINES EN TANT QU'ANTAGONISTES DU RECEPTEUR DU NEUROPEPTIDE Y

Publications (1)

Publication Number	Publication Date
BG104107A true BG104107A (bg)	2000-08-31

Family

ID=21993163

Family Applications (1)

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BG104107A BG104107A (bg)	1997-08-05	2000-01-26	4-АМИНОПИРОЛ/3,2-d/ ПИРИМИДИНИ КАТО РЕЦЕПТОРНИ АНТАГОНИСТИ НА НЕВРОПЕПТИД Y

Country Status (32)

Country	Link
US (1)	US6187778B1 (fr)
EP (1)	EP1003744B1 (fr)
JP (1)	JP3711238B2 (fr)
KR (1)	KR20010022583A (fr)
CN (1)	CN1264381A (fr)
AP (1)	AP9801312A0 (fr)
AT (1)	ATE296825T1 (fr)
AU (1)	AU7927498A (fr)
BG (1)	BG104107A (fr)
BR (1)	BR9811844A (fr)
CA (1)	CA2293621C (fr)
CO (1)	CO4960634A1 (fr)
DE (1)	DE69830409T2 (fr)
EA (1)	EA200000098A1 (fr)
ES (1)	ES2241146T3 (fr)
GT (1)	GT199800114A (fr)
HR (1)	HRP980434A2 (fr)
HU (1)	HUP0002956A3 (fr)
ID (1)	ID24300A (fr)
IL (1)	IL133430A0 (fr)
IS (1)	IS5294A (fr)
MA (1)	MA24629A1 (fr)
NO (1)	NO996178L (fr)
OA (1)	OA11277A (fr)
PA (1)	PA8456601A1 (fr)
PE (1)	PE106199A1 (fr)
PL (1)	PL338575A1 (fr)
SA (1)	SA98190435A (fr)
TN (1)	TNSN98148A1 (fr)
TR (1)	TR200000333T2 (fr)
WO (1)	WO1999007703A1 (fr)
ZA (1)	ZA986968B (fr)

Families Citing this family (36)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6187777B1 (en)	1998-02-06	2001-02-13	Amgen Inc.	Compounds and methods which modulate feeding behavior and related diseases
EP1218381B1 (fr) *	1999-09-30	2006-12-06	Neurogen Corporation	PYRAZOLO¬1,5-a\|-1,5-PYRIMIDINES ET PYRAZOLO¬1,5-a\|-1,3,5-TRIAZINES AMINO SUBSTITUEES
OA12514A (en) *	1999-12-24	2006-05-29	Aventis Pharma Ltd	Azaindoles.
GB0117396D0 (en)	2001-07-17	2001-09-05	Glaxo Group Ltd	Chemical compounds
GB0308208D0 (en)	2003-04-09	2003-05-14	Glaxo Group Ltd	Chemical compounds
WO2005118588A1 (fr)	2004-06-02	2005-12-15	Takeda Pharmaceutical Company Limited	Composé heterocyclique fusionné
RU2007101544A (ru)	2004-06-17	2008-08-10	Уайт (Us)	Антагонисты рецепторов высвобождающего гонадотропин гормона
RU2007101509A (ru)	2004-06-17	2008-07-27	Уайт (Us)	Способ получения антагонистов рецепторов гормона, высвобождающего гонадотропин
BRPI0514094A (pt) *	2004-08-02	2008-05-27	Osi Pharm Inc	composto, composição, e, método de tratamento de distúrbio hiperproliferativo
MY179032A (en)	2004-10-25	2020-10-26	Cancer Research Tech Ltd	Ortho-condensed pyridine and pyrimidine derivatives (e.g.purines) as protein kinase inhibitors
KR20060087386A (ko)	2005-01-28	2006-08-02	주식회사 대웅제약	신규 벤조이미다졸 유도체 및 이를 함유하는 약제학적조성물
PL1861387T3 (pl) *	2005-01-28	2014-08-29	Dae Woong Pharma	Pochodne benzoimidazolu i ich kompozycje farmaceutyczne
US7582634B2 (en)	2005-02-18	2009-09-01	Wyeth	7-substituted imidazo[4,5-c]pyridine antagonists of gonadotropin releasing hormone receptor
US7534796B2 (en)	2005-02-18	2009-05-19	Wyeth	Imidazo[4,5-b]pyridine antagonists of gonadotropin releasing hormone receptor
US7538113B2 (en)	2005-02-18	2009-05-26	Wyeth	4-substituted imidazo[4,5-c]pyridine antagonists of gonadotropin releasing hormone receptor
WO2006108218A1 (fr) *	2005-04-15	2006-10-19	Regenertech Pty Limited	Utilisation de neuropeptides y (npy) et d'agoniste d'antagonistes de ceux-ci pour regenerer des tissus
US7531542B2 (en)	2005-05-18	2009-05-12	Wyeth	Benzooxazole and benzothiazole antagonists of gonadotropin releasing hormone receptor
US7582636B2 (en)	2005-05-26	2009-09-01	Wyeth	Piperazinylimidazopyridine and piperazinyltriazolopyridine antagonists of Gonadotropin Releasing Hormone receptor
EP1905769B1 (fr) *	2005-07-13	2017-03-29	Msd K.K.	Dérivé du benzimidazole à substitution par un hétérocycle
UY29823A1 (es) *	2005-10-03	2007-05-31	Astrazeneca Ab	Derivados sustituidos de 7-cloro-3h-imidazol-(4,5-b) piridina, composiciones farmacéuticas que los contienen, procesos para la preparación de los mismos y aplicaciones
AR055669A1 (es) *	2005-10-03	2007-08-29	Astrazeneca Ab	Derivados de 3h - imidazo[4, 5 -b]piridina como inhibidores selectivos de gsk3, metodos e internediarios para su preparacion, composiciones farmaceuticas que los contienen y su uso para la elaboracion de un medicamento para el tratamiento de enfermedades neurodegenerativas y mentales.
WO2007067537A1 (fr) *	2005-12-07	2007-06-14	Osi Pharmaceuticals, Inc.	Composés inhibant les pyrrolopyridine kinases
EP1963315B1 (fr) *	2005-12-22	2014-10-08	Cancer Research Technology Limited	Inhibiteurs d'enzymes
WO2007093901A1 (fr)	2006-02-17	2007-08-23	Pfizer Limited	Dérivés de 3-déazapurine en tant que modulateurs de tlr7
WO2007125321A2 (fr)	2006-04-25	2007-11-08	Astex Therapeutics Limited	Composés pharmaceutiques
PT2054405E (pt) *	2006-07-11	2013-12-24	Dae Woong Pharma	Novos derivados de biaril benzoimidazol e composição farmacêutica que compreende os mesmos
KR101134239B1 (ko)	2006-07-11	2012-04-10	주식회사 대웅제약	신규한 바이아릴 벤조이미다졸 유도체 및 이를 함유하는 약학 조성물
CL2007002617A1 (es)	2006-09-11	2008-05-16	Sanofi Aventis	Compuestos derivados de pirrolo[2,3-b]pirazin-6-ilo; composicion farmaceutica que comprende a dichos compuestos; y su uso para tratar inflamacion de las articulaciones, artritis reumatoide, tumores, linfoma de las celulas del manto.
WO2008121064A1 (fr) *	2007-03-30	2008-10-09	Astrazeneca Ab	Nouveaux composés d'imidazo[4,5-b]pyridine-6-halo-7-aryl/heteroaryle 705
DE102007027800A1 (de)	2007-06-16	2008-12-18	Bayer Healthcare Ag	Substituierte bicyclische Heteroaryl-Verbindungen und ihre Verwendung
PL2201012T3 (pl)	2007-10-11	2014-11-28	Astrazeneca Ab	Pochodne pirolo[2,3-d]pirymidyny jako inhibitory kinazy białkowej b
EP2247596A2 (fr)	2008-01-11	2010-11-10	Natco Pharma Limited	Nouveaux derives de pyrazolo [3,4 -d] pyrimidine en tant qu'agents anticancereux
EP2694056B1 (fr)	2011-04-01	2019-10-16	AstraZeneca AB	Traitement thérapeutique
PH12014500943A1 (en)	2011-11-30	2014-06-30	Astrazeneca Ab	Combination treatment of cancer
AU2013204533B2 (en)	2012-04-17	2017-02-02	Astrazeneca Ab	Crystalline forms
JP7530360B2 (ja) *	2018-11-30	2024-08-07	武田薬品工業株式会社	Ｔｙｋ２阻害剤およびその使用

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3274213A (en)	1961-09-05	1966-09-20	Upjohn Co	Alkoxy-substituted 2-phenyl-1-(tertiary-aminoalkoxy)phenyl-3, 4-dihydronaphthalenes
DE2818676A1 (de) *	1978-04-27	1979-11-08	Troponwerke Gmbh & Co Kg	Substituierte 5,6-dimethylpyrrolo 2,3-d pyrimidine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
GB9022644D0 (en) *	1990-10-18	1990-11-28	Ici Plc	Heterocyclic compounds
US5877178A (en) *	1991-04-08	1999-03-02	Duquesne University Of The Holy Ghost	Pyrimidine derivatives and methods of making and using these derivatives
US5235053A (en) *	1992-06-22	1993-08-10	Eli Lilly And Company	Process for the synthesis of 4-hydroxy-5-halopyrrold[2,3-d]pyrimidine intermediates
US5284971A (en)	1992-07-16	1994-02-08	Syntex (U.S.A.) Inc.	4-(3-cyclohexyl-4-hydroxy or-methoxy phenylsulfonyl) 3,5 dibromo phenyl acetic thyromimetic cholesterol-lowering agents
EP0580550B1 (fr)	1992-07-21	1997-10-22	Novartis AG	Dérivés de l'acide oxamique utilisés comme agents hypocholestérémiques
EP0682027B1 (fr) *	1994-05-03	1997-10-15	Novartis AG	Dérivés de la pyrrolopyrimidine avec une activité anti-proliférative
JP4145955B2 (ja) *	1994-09-29	2008-09-03	ノバルティスアクチェンゲゼルシャフト	ピロロ〔２，３−ｄ〕ピリミジン及びその使用
US6562862B1 (en)	1994-10-20	2003-05-13	Eli Lilly And Company	Methods of inhibiting physiological conditions associated with an excess of neuropeptide Y
WO1996014307A1 (fr)	1994-11-07	1996-05-17	Pfizer Inc.	Certains derives de benzylamine a substitutions; une nouvelle classe de ligands specifiques du neuropeptide y1
US5644057A (en) *	1995-05-12	1997-07-01	Neurogen Corporation	Deazapurine derivatives; a new class of CRF1 specific ligands
EP0759441A3 (fr)	1995-06-30	1999-06-30	Eli Lilly And Company	Procédés de traitement des pathologies associées aux peptides neuropeptide Y
EP0871442A1 (fr)	1996-01-09	1998-10-21	Eli Lilly And Company	Antagonistes benzimidazolyles du recepteur du neuropeptide y

1998
- 1998-07-10 ID IDW20000021A patent/ID24300A/id unknown
- 1998-07-10 JP JP2000506207A patent/JP3711238B2/ja not_active Expired - Fee Related
- 1998-07-10 EP EP98929573A patent/EP1003744B1/fr not_active Expired - Lifetime
- 1998-07-10 CA CA002293621A patent/CA2293621C/fr not_active Expired - Fee Related
- 1998-07-10 US US09/380,901 patent/US6187778B1/en not_active Expired - Fee Related
- 1998-07-10 PL PL98338575A patent/PL338575A1/xx unknown
- 1998-07-10 IL IL13343098A patent/IL133430A0/xx unknown
- 1998-07-10 BR BR9811844-7A patent/BR9811844A/pt not_active Application Discontinuation
- 1998-07-10 EA EA200000098A patent/EA200000098A1/ru unknown
- 1998-07-10 HU HU0002956A patent/HUP0002956A3/hu unknown
- 1998-07-10 TR TR2000/00333T patent/TR200000333T2/xx unknown
- 1998-07-10 KR KR1020007001174A patent/KR20010022583A/ko not_active Ceased
- 1998-07-10 CN CN98807398A patent/CN1264381A/zh active Pending
- 1998-07-10 WO PCT/IB1998/001053 patent/WO1999007703A1/fr not_active Ceased
- 1998-07-10 AU AU79274/98A patent/AU7927498A/en not_active Abandoned
- 1998-07-10 ES ES98929573T patent/ES2241146T3/es not_active Expired - Lifetime
- 1998-07-10 AT AT98929573T patent/ATE296825T1/de not_active IP Right Cessation
- 1998-07-10 DE DE69830409T patent/DE69830409T2/de not_active Expired - Fee Related
- 1998-07-27 GT GT199800114A patent/GT199800114A/es unknown
- 1998-07-30 PE PE1998000678A patent/PE106199A1/es not_active Application Discontinuation
- 1998-07-30 AP APAP/P/1998/001312A patent/AP9801312A0/en unknown
- 1998-08-03 PA PA19988456601A patent/PA8456601A1/es unknown
- 1998-08-04 TN TNTNSN98148A patent/TNSN98148A1/fr unknown
- 1998-08-04 MA MA25203A patent/MA24629A1/fr unknown
- 1998-08-04 ZA ZA9806968A patent/ZA986968B/xx unknown
- 1998-08-04 HR HR60/054,734A patent/HRP980434A2/hr not_active Application Discontinuation
- 1998-08-05 CO CO98044925A patent/CO4960634A1/es unknown
- 1998-08-19 SA SA98190435A patent/SA98190435A/ar unknown
1999
- 1999-12-10 IS IS5294A patent/IS5294A/is unknown
- 1999-12-14 NO NO996178A patent/NO996178L/no not_active Application Discontinuation
2000
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Also Published As

Publication number	Publication date
PL338575A1 (en)	2000-11-06
GT199800114A (es)	2000-01-18
KR20010022583A (ko)	2001-03-26
EA200000098A1 (ru)	2000-08-28
DE69830409T2 (de)	2006-01-26
AU7927498A (en)	1999-03-01
ZA986968B (en)	2000-02-04
CN1264381A (zh)	2000-08-23
OA11277A (en)	2003-07-29
BR9811844A (pt)	2000-08-08
PA8456601A1 (es)	2000-05-24
IL133430A0 (en)	2001-04-30
HUP0002956A2 (hu)	2001-08-28
JP3711238B2 (ja)	2005-11-02
MA24629A1 (fr)	1999-04-01
NO996178L (no)	2000-02-14
NO996178D0 (no)	1999-12-14
IS5294A (is)	1999-12-10
EP1003744A1 (fr)	2000-05-31
SA98190435A (ar)	2005-12-03
WO1999007703A1 (fr)	1999-02-18
JP2001512729A (ja)	2001-08-28
AP9801312A0 (en)	2000-01-30
ID24300A (id)	2000-07-13
CO4960634A1 (es)	2000-09-25
ATE296825T1 (de)	2005-06-15
PE106199A1 (es)	1999-11-02
TNSN98148A1 (fr)	2005-03-15
ES2241146T3 (es)	2005-10-16
US6187778B1 (en)	2001-02-13
DE69830409D1 (de)	2005-07-07
CA2293621C (fr)	2003-12-30
EP1003744B1 (fr)	2005-06-01
HRP980434A2 (en)	1999-04-30
TR200000333T2 (tr)	2000-05-22
CA2293621A1 (fr)	1999-02-18
HUP0002956A3 (en)	2002-01-28

Publication	Publication Date	Title
BG104107A (bg)	2000-08-31	4-АМИНОПИРОЛ/3,2-d/ ПИРИМИДИНИ КАТО РЕЦЕПТОРНИ АНТАГОНИСТИ НА НЕВРОПЕПТИД Y
US6337332B1 (en)	2002-01-08	Neuropeptide Y receptor antagonists
EP3503884B1 (fr)	2021-07-21	Composition pharmaceutique utilisée pour le traitement du prurit et/ou des démangeaisons
US6040310A (en)	2000-03-21	4-aminopyrrole (3,2-d) pyrimidines as neuropeptide Y receptor antagonists
US6511984B2 (en)	2003-01-28	Neuropeptide Y antagonists
US6197822B1 (en)	2001-03-06	Neuropeptide antagonists
US6147085A (en)	2000-11-14	Aminoalkyl substituted 9H-pyridino[2,3-b] indole and 9H-pyrimidino[4,5-b] indole derivatives
EP1033366A2 (fr)	2000-09-06	Dérivés d'amide comme antagonistes de récepteur de Neuropeptide Y (NPY)
US6221875B1 (en)	2001-04-24	Substituted 9H-pyridino [2,3-B]indole and 9H-pyrimidino [4,5-B]indole derivatives: selective neuropeptide Y receptor ligands
US6649759B2 (en)	2003-11-18	Neuropeptide Y antagonists
MXPA99012095A (es)	2000-09-04	4-aminopirrol (3,2-d) pirimidinas como antagonistas del receptor del neuropeptido y
CZ439199A3 (cs)	2000-07-12	4-Aminopyrrol(3^-d)pyrimidiny jako antagonisty receptoru neuropeptidu Y
CN121818599A (zh)	2026-04-10	烷胺化合物的用途
JP2006501244A5 (fr)	2006-08-31