63659-17-6Relevant articles and documents
PROCESS FOR PREPARATION OF PHENOXYPROPANOL AMINES
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Page/Page column 8-9, (2010/04/06)
The present invention describes an improved method for the preparation of l-[4-{2- (cyclopropylmethoxy)ethyl}phenoxy]-3-[(1-methylethyl)amino]-2-propanol of Formula-(I) and its pharmaceutically acceptable salt, which comprises reacting 4 - [ 2 — (Cyclopropylmethoxy) ethyl] phenol with epichlorohydrin in presence of mild base and polar protic solvent to isolate 1 - {4 - [2 - (cyclopropylmethoxy)ethyl] - phenoxy} - 2, 3 - epoxy propane, which is further reacted with isopropyl amine to get betaxolol formula (I).
A convenient synthesis of the enantiomerically pure β-blocker (S)-betaxolol using hydrolytic kinetic resolution
Joshi, Ramesh A.,Garud, Dinesh R.,Muthukrishnan,Joshi, Rohini R.,Gurjar
, p. 3802 - 3806 (2007/10/03)
Enantiopure (S)-betaxolol was prepared in an extremely simple and practical way using hydrolytic kinetic resolution of a terminal epoxide by Jacobsen's catalyst. High enantiomeric purity (99% ee) has been achieved and the method is amenable to industrial scale-up.
Process for the selective alkylation of betaxolol intermediates
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, (2008/06/13)
The present invention relates to a process for the selective alkylation of intermediates of betaxolol.
A chemoenzymatic route to both enantiomers of betaxolol
Di Bono,Scilimati
, p. 699 - 702 (2007/10/02)
Evaluation of some of the possible lipase-catalyzed transformations has been done in order to prepare both enantiomers of betaxolol. Resolution of betaxolol by lipase-catalyzed hydrolysis of its bisacetylated derivatives 4 led to (-)- and (+)-enantiomers with an ee of 20 and 60%, respectively. When the resolution was performed on the chlorohydrin precursor 6 of betaxolol, (-)- and (+)-enantiomers were obtained with an ee of 91 and 75%, respectively.
Design and synthesis of a series of combined vasodilator/β-adrenoceptor antagonists based on 6-arylpyridazinones
Slater,Howson,Swayne,Taylor,Reavill
, p. 345 - 351 (2007/10/02)
A series of new 6-[4-[[(aryloxy)acyl]amino]phenyl]-4,5-dihydropyridazinones have been synthesized and evaluated as combined vasodilator/β-adrenoceptor antagonists and potential antihypertensive agents. Many of the early compounds displayed an unacceptably high level of intrinsic sympathomimetic activity (ISA) and a relatively short duration of action. Disubstitution in the 2,3-positions or in the 4-position of the aryloxy ring gave compounds with low ISA levels and, in some instances, improved duration of action. All of the compounds were vasodilators, but the 5-methylpyridazinone derivatives showed consistently greater antihypertensive activity than their 5-H lower homologues. Further detailed pharmacological investigations led to the selection of 6-[4-[3-[[2-hydroxy-3-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]propyl]amino ]propionamido]phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone (4t) (SK&F 95018) as a development candidate.
Derivatives related to betaxolol with α- and β-adrenergic activities
Leclerc,Decker,Schwartz
, p. 1357 - 1367 (2007/10/02)
The paper describes the synthesis and the pharmacological evaluation of some derivatives of betaxolol, all with an N-aralkylamine instead of the tertiobutylamine. These compounds have been tested for β1-adrenergic receptor antagonism on guinea pig atria, β2-adrenergic receptor antagonism on guinea pig trachea and α-adrenergic blocking activity on rat aorta. Compound U12 with a marked α-blocking activity and compound R8 with a β1/α ratio = 1 were selected for a haemodynamic study in the dog. The decrease in cardiac work and the diminution of total peripheral resistance exhibited by U12 are consistent with a dual α/β-blocking agent. Finally, structure-activity relationships are discussed.
Anti-glaucoma agent
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, (2008/06/13)
1-{4-[2-(Cyclopropylmethoxy)-ethyl]-phenoxy}-3-isopropylamino-propan-2-ol and its pharmaceutically acceptable salts, in the form of a racemate or optical isomer, are useful as topical anti-glaucoma agents.
PHENOL ETHERS
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, (2008/06/13)
The invention provides phenol ethers of the formula: STR1 wherein R is branched C 3-4 alkyl, C 3-4 cycloalkyl, branched cyano(C 3-4 alkyl), phenyl(C 2-3 alkyl), halophenyl(C 2-3 alkyl), (C 1-4 alkoxy)phenyl(C 2-4 alkyl), or (C 1-4 acyl) amino(C 1-4 alkyl),alk is C 1-4 alkyl substituted by a 3 to 6 membered cycloalkyl group,X is--O--,--S--or--SO 2--; andR 1 is--C 1-4 alkyl-or--C 1-4 alkoxy-, in their racemic and optically active forms, and their addition salts with pharmaceutically acceptable acids. These compounds are useful in therapy as β-adrenergic blocking agents. Intermediates are also provided.
