WO1999007695A3 - ALPHA 1a ADRENERGIC RECEPTOR ANTAGONIST - Google Patents

ALPHA 1a ADRENERGIC RECEPTOR ANTAGONIST Download PDF

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Publication number
WO1999007695A3
WO1999007695A3 PCT/US1998/016011 US9816011W WO9907695A3 WO 1999007695 A3 WO1999007695 A3 WO 1999007695A3 US 9816011 W US9816011 W US 9816011W WO 9907695 A3 WO9907695 A3 WO 9907695A3
Authority
WO
WIPO (PCT)
Prior art keywords
compound
alpha
adrenergic receptor
useful
receptor antagonist
Prior art date
Application number
PCT/US1998/016011
Other languages
French (fr)
Other versions
WO1999007695A2 (en
Inventor
Daniel R Sidler
Robert D Larsen
Michel Chartrain
Norihiro Ikemoto
Christopher M Roberge
Colleen S Taylor
Wenjie Li
Gerald F Bills
Original Assignee
Merck & Co Inc
Daniel R Sidler
Robert D Larsen
Michel Chartrain
Norihiro Ikemoto
Christopher M Roberge
Colleen S Taylor
Wenjie Li
Gerald F Bills
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.)
Filing date
Publication date
Priority claimed from GBGB9719706.5A external-priority patent/GB9719706D0/en
Priority claimed from GBGB9719708.1A external-priority patent/GB9719708D0/en
Priority claimed from US09/122,301 external-priority patent/US6207444B1/en
Application filed by Merck & Co Inc, Daniel R Sidler, Robert D Larsen, Michel Chartrain, Norihiro Ikemoto, Christopher M Roberge, Colleen S Taylor, Wenjie Li, Gerald F Bills filed Critical Merck & Co Inc
Priority to EP98938234A priority Critical patent/EP1003734A2/en
Priority to JP2000506199A priority patent/JP2001512724A/en
Priority to AU86805/98A priority patent/AU8680598A/en
Priority to CA002297889A priority patent/CA2297889A1/en
Publication of WO1999007695A2 publication Critical patent/WO1999007695A2/en
Publication of WO1999007695A3 publication Critical patent/WO1999007695A3/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
    • 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
    • A61P13/08—Drugs for disorders of the urinary system of the prostate
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings

Abstract

This invention relates to crystalline pharmaceutically acceptable salts of an alpha 1a adrenergic receptor antagonist, Compound A, which are useful in the treatment of benign prostatic hyperplasia. Pharmaceutical compositions employing the crystalline salts, and processes for making and using the crystalline salts and pharmaceutical compositions of Compound A are also disclosed. This invention further relates to a process for obtaining enantiomerically pure intermediate useful for the synthesis of end product alpha 1a adrenergic receptor antagonists. The end product compounds are useful for the treatment of benign prostatic hyperplasia and for relaxing lower urinary tract tissue. The invention also relates to a process for preparing a class of dihydropyrimidinone compounds of which Compound A is a member, wherein the process involves deprotonating a dihydropyrimidinone compound and then coupling the deprotonated derivative with a primary amine.
PCT/US1998/016011 1997-08-05 1998-07-31 ALPHA 1a ADRENERGIC RECEPTOR ANTAGONIST WO1999007695A2 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP98938234A EP1003734A2 (en) 1997-08-05 1998-07-31 ALPHA 1a ADRENERGIC RECEPTOR ANTAGONIST
JP2000506199A JP2001512724A (en) 1997-08-05 1998-07-31 α1a adrenergic receptor antagonist
AU86805/98A AU8680598A (en) 1997-08-05 1998-07-31 Alpha 1a adrenergic receptor antagonist
CA002297889A CA2297889A1 (en) 1997-08-05 1998-07-31 Alpha 1a adrenergic receptor antagonist

Applications Claiming Priority (10)

Application Number Priority Date Filing Date Title
US5490297P 1997-08-05 1997-08-05
US5481597P 1997-08-05 1997-08-05
GBGB9719706.5A GB9719706D0 (en) 1997-09-16 1997-09-16 Alpha 1a adrenergic receptor antagonist
GB9719706.5 1997-09-16
GBGB9719708.1A GB9719708D0 (en) 1997-09-16 1997-09-16 Enzymatic resolution of a dihydropyrimidinone
GB9719708.1 1997-09-16
US60/054,902 1998-07-24
US09/122,301 1998-07-24
US60/054,815 1998-07-24
US09/122,301 US6207444B1 (en) 1997-08-05 1998-07-24 Enzymatic process of making alpha 1a adrenergic receptor antagonists using protease

Publications (2)

Publication Number Publication Date
WO1999007695A2 WO1999007695A2 (en) 1999-02-18
WO1999007695A3 true WO1999007695A3 (en) 1999-06-17

Family

ID=27517427

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1998/016011 WO1999007695A2 (en) 1997-08-05 1998-07-31 ALPHA 1a ADRENERGIC RECEPTOR ANTAGONIST

Country Status (5)

Country Link
EP (1) EP1003734A2 (en)
JP (1) JP2001512724A (en)
AU (1) AU8680598A (en)
CA (1) CA2297889A1 (en)
WO (1) WO1999007695A2 (en)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU714640B2 (en) 1994-11-16 2000-01-06 H. Lundbeck A/S Dihydropyrimidines and uses thereof
US6268369B1 (en) 1994-11-16 2001-07-31 Synaptic Pharmaceutical Corporation 5-(heterocyclic alkyl)-6-aryl-dihydropyrimidines
US6228861B1 (en) 1995-11-16 2001-05-08 Synaptic Pharmaceutical Corporation Dihydropyrimidines and uses thereof
US6469065B1 (en) 1996-02-02 2002-10-22 Nitromed, Inc. Nitrosated and nitrosylated α-adrenergic receptor antagonist, compositions and methods of use
US6245773B1 (en) 1996-05-16 2001-06-12 Synaptic Pharmaceutical Corporation 5-(heterocyclic alkyl)-6-aryl-dihydropyrimidines
US6172066B1 (en) 1996-05-16 2001-01-09 Synaptic Pharmaceutical Corporation Dihydropyrimidines and uses thereof
US6680323B2 (en) 1998-12-23 2004-01-20 Synaptic Pharmaceutical Corporation Dihydropyrimidines and uses thereof
WO2000037026A1 (en) * 1998-12-23 2000-06-29 Synaptic Pharmaceutical Corporation Dihydropyrimidines and uses thereof
US6274585B1 (en) * 1998-12-23 2001-08-14 Synaptic Pharmaceutical Corporation Dihydropyrimidines and uses thereof
US6720324B2 (en) 2000-07-05 2004-04-13 Synaptic Pharmaceutical Corporation Selective melanin concentrating hormone-1 (MCH1) receptor antagonists and uses thereof
ES2278032T3 (en) 2001-07-13 2007-08-01 Astrazeneca Uk Limited PREPARATION OF AMINOPIRIMIDINE COMPOUNDS.
DE60330050D1 (en) 2002-12-16 2009-12-24 Astrazeneca Uk Ltd METHOD FOR PRODUCING PYRIMIDINE COMPOUNDS
EP2426120A1 (en) 2003-08-18 2012-03-07 Fujifilm Finechemicals Co., Ltd. Pyridyltetrahydropyridines and pyridylpiperidines, and method of manufacturing them
GB0428328D0 (en) 2004-12-24 2005-02-02 Astrazeneca Uk Ltd Chemical process

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996014846A1 (en) * 1994-11-16 1996-05-23 Synaptic Pharmaceutical Corporation Dihydropyrimidines and uses thereof
WO1997021687A1 (en) * 1995-12-14 1997-06-19 Merck & Co., Inc. Process for making dihydropyrimidinones

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996014846A1 (en) * 1994-11-16 1996-05-23 Synaptic Pharmaceutical Corporation Dihydropyrimidines and uses thereof
WO1997021687A1 (en) * 1995-12-14 1997-06-19 Merck & Co., Inc. Process for making dihydropyrimidinones

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
K.S. ATWAL ET AL.: "DIHYDROPYRIMIDINE CALCIUM CHANNEL BLOCKERS.3.", JOURNAL OF MEDICINAL CHEMISTRY., vol. 34, 1991, WASHINGTON US, pages 806 - 811, XP002099938 *
VERSHA VINAY KUMAR ET AL.: "DESIGN,SYNTHESIS AND BIOLOGICAL EVALUATION OF 1,3-DIAMINOPROPANES", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 7, no. 6, 1997, GB, pages 675 - 680, XP004136107 *

Also Published As

Publication number Publication date
AU8680598A (en) 1999-03-01
CA2297889A1 (en) 1999-02-18
EP1003734A2 (en) 2000-05-31
WO1999007695A2 (en) 1999-02-18
JP2001512724A (en) 2001-08-28

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