SK6012002A3 - Imidazole derivative as phosphodiesterase vii inhibitor, use thereof and pharmaceutical composition containing the same - Google Patents

Imidazole derivative as phosphodiesterase vii inhibitor, use thereof and pharmaceutical composition containing the same Download PDF

Info

Publication number: SK6012002A3
Authority: SK; Slovakia
Prior art keywords: formula; disorders; solvates; compounds; treatment
Prior art date: 1999-11-13

Application number

SK601-2002A

Other languages

English (en)

Slovak (sk)

Inventor

Hans Michael Eggenweiler

Rochus Jonas

Michael Wolf

Michael Gassen

Thomas Welge

Original Assignee

Merck Patent Gmbh

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.)

1999-11-13

Filing date

2000-10-31

Publication date

2002-09-10

2000-10-31 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

2002-09-10 Publication of SK6012002A3 publication Critical patent/SK6012002A3/sk

Links

150000002460 imidazoles Chemical class 0.000 title claims abstract description 8
239000008194 pharmaceutical composition Substances 0.000 title claims description 9
239000002606 phosphodiesterase VII inhibitor Substances 0.000 title abstract description 15
150000003839 salts Chemical class 0.000 claims abstract description 19
239000003814 drug Substances 0.000 claims abstract description 15
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
239000012453 solvate Substances 0.000 claims abstract description 10
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
229910052731 fluorine Inorganic materials 0.000 claims abstract description 6
229910052794 bromium Inorganic materials 0.000 claims abstract description 5
229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 39
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
238000000034 method Methods 0.000 claims description 9
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OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
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239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000002243 precursor Substances 0.000 description 1
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125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
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HSBUTEBBRZNTNG-UHFFFAOYSA-N pyrano[2,3-d]imidazole Chemical class C1=COC2=NC=NC2=C1 HSBUTEBBRZNTNG-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
HJORMJIFDVBMOB-UHFFFAOYSA-N rolipram Chemical compound COC1=CC=C(C2CC(=O)NC2)C=C1OC1CCCC1 HJORMJIFDVBMOB-UHFFFAOYSA-N 0.000 description 1
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Classifications

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- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/06—Peri-condensed systems

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Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pulmonology (AREA)
Diabetes (AREA)
Immunology (AREA)
Rheumatology (AREA)
Physical Education & Sports Medicine (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Hematology (AREA)
Orthopedic Medicine & Surgery (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Dermatology (AREA)
Virology (AREA)
Urology & Nephrology (AREA)
Heart & Thoracic Surgery (AREA)
AIDS & HIV (AREA)
Tropical Medicine & Parasitology (AREA)
Molecular Biology (AREA)
Endocrinology (AREA)
Emergency Medicine (AREA)
Obesity (AREA)
Vascular Medicine (AREA)
Pain & Pain Management (AREA)
Cardiology (AREA)

SK601-2002A 1999-11-13 2000-10-31 Imidazole derivative as phosphodiesterase vii inhibitor, use thereof and pharmaceutical composition containing the same SK6012002A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19954707A DE19954707A1 (de)	1999-11-13	1999-11-13	Imidazolverbindungen als Phosphodiesterase VII-Hemmer
PCT/EP2000/010765 WO2001036425A2 (fr)	1999-11-13	2000-10-31	Composes imidazole utilises comme inhibiteurs de la phosphodiesterase vii

Publications (1)

Publication Number	Publication Date
SK6012002A3 true SK6012002A3 (en)	2002-09-10

Family

ID=7928973

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK601-2002A SK6012002A3 (en)	1999-11-13	2000-10-31	Imidazole derivative as phosphodiesterase vii inhibitor, use thereof and pharmaceutical composition containing the same

Country Status (23)

Country	Link
US (1)	US6884800B1 (fr)
EP (1)	EP1228073B1 (fr)
JP (1)	JP4819272B2 (fr)
KR (1)	KR20020049051A (fr)
CN (1)	CN1390222A (fr)
AR (1)	AR026421A1 (fr)
AT (1)	ATE245653T1 (fr)
AU (1)	AU775886B2 (fr)
BR (1)	BR0015487A (fr)
CA (1)	CA2391087A1 (fr)
CZ (1)	CZ20021474A3 (fr)
DE (2)	DE19954707A1 (fr)
DK (1)	DK1228073T3 (fr)
ES (1)	ES2200968T3 (fr)
HU (1)	HUP0203422A3 (fr)
MX (1)	MXPA02004728A (fr)
NO (1)	NO20022232D0 (fr)
PL (1)	PL355098A1 (fr)
PT (1)	PT1228073E (fr)
RU (1)	RU2002113759A (fr)
SK (1)	SK6012002A3 (fr)
WO (1)	WO2001036425A2 (fr)
ZA (1)	ZA200204729B (fr)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ES2217956B1 (es) *	2003-01-23	2006-04-01	Almirall Prodesfarma, S.A.	Nuevos derivados de 4-aminotieno(2,3-d)pirimidin-6-carbonitrilo.
EP2258359A3 (fr)	2005-08-26	2011-04-06	Braincells, Inc.	Neurogenèse par modulation des récepteurs muscariniques avec sabcomeline
JP2009506069A (ja)	2005-08-26	2009-02-12	ブレインセルス，インコーポレイティド	ムスカリン性受容体調節による神経発生
US7985756B2 (en)	2005-10-21	2011-07-26	Braincells Inc.	Modulation of neurogenesis by PDE inhibition
WO2007053596A1 (fr)	2005-10-31	2007-05-10	Braincells, Inc.	Modulation de la neurogenese dont la mediation est assuree par recepteur gaba
US20100216734A1 (en)	2006-03-08	2010-08-26	Braincells, Inc.	Modulation of neurogenesis by nootropic agents
WO2007134077A2 (fr)	2006-05-09	2007-11-22	Braincells, Inc.	Neurogenèse induite par le récepteur 5ht
WO2007134136A2 (fr)	2006-05-09	2007-11-22	Braincells, Inc.	Neurogenèse par modulation de l'angiotensine
EP2068872A1 (fr)	2006-09-08	2009-06-17	Braincells, Inc.	Combinaisons contenant un dérivé de 4-acylaminopyridine
US20100184806A1 (en)	2006-09-19	2010-07-22	Braincells, Inc.	Modulation of neurogenesis by ppar agents
WO2008119057A2 (fr) *	2007-03-27	2008-10-02	Omeros Corporation	Utilisation d'inhibiteurs pde7 dans le traitement des troubles du
US8637528B2 (en)	2007-03-27	2014-01-28	Omeros Corporation	Use of PDE7 inhibitors for the treatment of movement disorders
DE102007047738A1 (de) *	2007-10-05	2009-04-09	Merck Patent Gmbh	Imidazolderivate
WO2010099217A1 (fr)	2009-02-25	2010-09-02	Braincells, Inc.	Modulation de neurogenèse à l'aide de combinaisons de d-cyclosérine
US9220715B2 (en)	2010-11-08	2015-12-29	Omeros Corporation	Treatment of addiction and impulse-control disorders using PDE7 inhibitors
KR20130124333A (ko)	2010-11-08	2013-11-13	오메로스 코포레이션	Pde7 억제제를 사용한 중독 및 충동-조절 장애의 치료
EP2804603A1 (fr)	2012-01-10	2014-11-26	President and Fellows of Harvard College	Composés promoteurs de réplication des cellules bêta et leurs procédés d'utilisation
US11685745B2 (en)	2017-07-12	2023-06-27	Dart Neuroscience, Llc	Substituted benzoxazole and benzofuran compounds as PDE7 inhibitors
AU2023326563A1 (en)	2022-08-18	2025-02-27	Mitodicure Gmbh	Use of a therapeutic agent with phosphodiesterase-7 inhibitory activity for the treatment and prevention of diseases associated with chronic fatigue, exhaustion and/or exertional intolerance

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2919271A (en) *	1957-12-05	1959-12-29	Smith Kline French Lab	3-amino-1, 2-dihydro-3h-pyrido [3, 2, 1-kl]-phenothiazines
ES2067744T3 (es) *	1989-06-09	1995-04-01	Upjohn Co	Aminas heterociclicas con actividad sobre el sistema nervioso central.
US5318965A (en) *	1990-08-24	1994-06-07	Abbott Laboratories	Quinobenzoxazine, antineoplastic agents
ZA9810766B (en) *	1997-11-28	1999-05-25	Mochida Pharm Co Ltd	Novel compounds having cgmp-pde inhibitory activity

1999
- 1999-11-13 DE DE19954707A patent/DE19954707A1/de not_active Withdrawn
2000
- 2000-10-31 WO PCT/EP2000/010765 patent/WO2001036425A2/fr not_active Ceased
- 2000-10-31 DK DK00975978T patent/DK1228073T3/da active
- 2000-10-31 BR BR0015487-3A patent/BR0015487A/pt not_active Application Discontinuation
- 2000-10-31 AT AT00975978T patent/ATE245653T1/de not_active IP Right Cessation
- 2000-10-31 PL PL00355098A patent/PL355098A1/xx unknown
- 2000-10-31 US US10/129,629 patent/US6884800B1/en not_active Expired - Fee Related
- 2000-10-31 RU RU2002113759/04A patent/RU2002113759A/ru unknown
- 2000-10-31 PT PT00975978T patent/PT1228073E/pt unknown
- 2000-10-31 SK SK601-2002A patent/SK6012002A3/sk unknown
- 2000-10-31 DE DE50003036T patent/DE50003036D1/de not_active Expired - Lifetime
- 2000-10-31 CA CA002391087A patent/CA2391087A1/fr not_active Abandoned
- 2000-10-31 CZ CZ20021474A patent/CZ20021474A3/cs unknown
- 2000-10-31 KR KR1020027006131A patent/KR20020049051A/ko not_active Withdrawn
- 2000-10-31 ES ES00975978T patent/ES2200968T3/es not_active Expired - Lifetime
- 2000-10-31 AU AU13907/01A patent/AU775886B2/en not_active Ceased
- 2000-10-31 MX MXPA02004728A patent/MXPA02004728A/es not_active Application Discontinuation
- 2000-10-31 HU HU0203422A patent/HUP0203422A3/hu unknown
- 2000-10-31 CN CN00815534A patent/CN1390222A/zh active Pending
- 2000-10-31 JP JP2001538914A patent/JP4819272B2/ja not_active Expired - Fee Related
- 2000-10-31 EP EP00975978A patent/EP1228073B1/fr not_active Expired - Lifetime
- 2000-11-10 AR ARP000105929A patent/AR026421A1/es unknown
2002
- 2002-05-10 NO NO20022232A patent/NO20022232D0/no not_active Application Discontinuation
- 2002-06-12 ZA ZA200204729A patent/ZA200204729B/en unknown

Also Published As

Publication number	Publication date
ZA200204729B (en)	2003-11-26
AR026421A1 (es)	2003-02-12
EP1228073B1 (fr)	2003-07-23
MXPA02004728A (es)	2002-08-30
PT1228073E (pt)	2003-12-31
HUP0203422A2 (hu)	2003-02-28
EP1228073A2 (fr)	2002-08-07
PL355098A1 (en)	2004-04-05
KR20020049051A (ko)	2002-06-24
JP4819272B2 (ja)	2011-11-24
NO20022232L (no)	2002-05-10
ES2200968T3 (es)	2004-03-16
WO2001036425A3 (fr)	2002-01-10
AU775886B2 (en)	2004-08-19
US6884800B1 (en)	2005-04-26
JP2003514821A (ja)	2003-04-22
RU2002113759A (ru)	2004-01-10
CA2391087A1 (fr)	2001-05-25
DE19954707A1 (de)	2001-05-17
ATE245653T1 (de)	2003-08-15
DE50003036D1 (de)	2003-08-28
AU1390701A (en)	2001-05-30
NO20022232D0 (no)	2002-05-10
CZ20021474A3 (cs)	2002-07-17
WO2001036425A2 (fr)	2001-05-25
HUP0203422A3 (en)	2004-12-28
BR0015487A (pt)	2002-07-02
DK1228073T3 (da)	2003-11-03
CN1390222A (zh)	2003-01-08

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