US 6,294,531 B1Granted

Calcilytic compounds

AssigneeSmithKline Beecham Corporation

InventorsRobert M. Barmore, Pradip Kumar Bhatnagar, William M. Bryan, Joelle Lorraine Burgess, James Francis Callahan, Raul Rolando Calvo, Eric G. Del Mar, Maria Amparo Lago, Thomas The Nguyen, Derek Sheehan, Robert Lawrence Smith, Linda Sue Southall, Bradford C. Van Wagenen

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Abstract

Novel arylalkylamino compounds exhibiting calcilytic properties are provided.

Claims8

Dependent claims

A compound selected from the group consisting of:

(R)-3-[2-cyano-4-[N-benzyl-N-[4-methylphenylsulfonyl]amino]phenoxy]-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-propan-2-ol;
(R)-3-[2-cyano-4-[N-[4-methylphenylsulfonyl]amino]phenoxy]-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-propan-2-ol;
(R)-3-[2-cyano-4-[N-methyl-N-[4-methylphenylsulfonyl]amino]phenoxy]-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-propan-2-ol;
(R)-3-[2-cyano-4-[N-methyl-N-[methylsulfonyl]amino]phenoxy]-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-propan-2-ol;
(R)-3-[2-cyano-4-[N-benzyl-N-[methylsulfonyl]amino]phenoxy]-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-propan-2-ol;
(R)-3-[2-cyano-4-[N-methylsulfonylamino]phenoxy]-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-propan-2-ol;
(R)-3-[2-cyano-4-[N-benzyl-N-[methylsulfonyl]amino]phenoxy]-1-[1,1-dimethyl-2-(2-naphthyl)ethylamino]-propan-2-ol;
(R)-3-[2-cyano-4-[N-[methylsulfonyl]amino]phenoxy]-1-[1,1-dimethyl-2-(2-naphthyl)ethylamino]-propan-2-ol;
(R)-3-[2-cyano-4-[N-benzyl-N-[4-methylphenylsulfonyl]amino]phenoxy]-1-[1,1-dimethyl-2-(2-naphthyl)ethylamino]-propan-2-ol;
(R)-3-[2-cyano-4-[N-benzyl-N-[4-methylphenylsulfonyl]amino]phenoxy]-1-[1,1-dimethyl-2-(benzyloxy)ethylamino]-propan-2-ol;
(R)-3-[2-cyano-4-[N-benzyl-N-[4-methylphenylsulfonyl]amino]phenoxy]-1-[1,1-dimethyl-3-phenylpropylamino]-propan-2-ol;
(R)-3-[2-cyano-4-[N-benzyl-N-[4-methylphenylsulfonyl]amino]phenoxy]-1-[1,1-dimethyl-4-phenylbutylamino]-propan-2-ol;
(R)-3-[2-cyano-4-[N-benzyl-N-ethylcarbonyl]phenoxy]-1-[1,1-dimethyl-2-(2-naphthyl)ethylamino]-propan-2-ol;
(R)-3-[2-cyano-4-[N-benzyl-N′-morpholino]ureido]phenoxy]-1-[1,1-dimethyl-2-(2-naphthyl)ethylamino]-propan-2-ol;
(R)-3-[2-cyano-4-[N-benzyl-N′-morpholino]ureido]phenoxy]-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-propan-2-ol;
(R)-3-[2-cyano-4-[N-methyl-N′-morpholino]ureido]phenoxy]-1-[1,1-dimethyl-2-(2-naphthyl)ethylamino]-propan-2-ol;
(R)-3-[2-cyano-4-[N-methyl-N′-morpholino]ureido]phenoxy]-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-3-[2-cyano-4-(N,N-dipropylaminocarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-3-[2-cyano-4-(N-propylaminocarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-3-[2-cyano-4-(N-piperidinylcarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-3-[2-cyano-4-(N-morpholinylcarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-3-[2,3-dichloro-4-(N-morpholinylcarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(2-naphthyl)ethylamino]-3-[2,3-dichloro-4-(N-morpholinylcarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-3-[2,3-dichloro-4-(N,N-dipropylaminocarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(2-naphthyl)ethylamino]-3-[2,3-dichloro-4-(N,N-dipropylaminocarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-3-[2-cyano, 3-chloro-4-(N-morpholinylcarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(2-naphthyl)ethylamino]-3-[2-cyano, 3-chloro-4-(N-morpholinylcarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-3-[2-cyano, 3-chloro-4-(N,N-dipropylaminocarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(2-naphthyl)ethylamino]-3-[2-cyano, 3-chloro-4-(N,N-dipropylaminocarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-3-[2-cyano-4-(N-pyrrolidinylcarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-3-[2-cyano-4-(N-piperazinylcarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(2-naphthyl)ethylamino]-3-[2-cyano-4-(N,N-dipropylaminocarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(2-naphthyl)ethylamino]-3-[2-cyano-4-(N-piperidinylcarbonyl)phenoxy3-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(2-naphthyl)ethylamino]-3-[2-cyano-4-(N-morpholinylcarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(2-naphthyl)ethylamino]-3-[2-cyano-4-(N-piperazinylcarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(2-naphthyl)ethylamino]-3-[2-cyano-4-(N-pyrrolidinylcarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-3-(phenyl)propylamino]-3-[2-cyano-4-(N,N-dipropylaminocarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-4-(phenyl)butylamino]-3-[2-cyano-4-(N,N-dipropylaminocarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-3-(phenoxy)propylamino]-3-[2-cyano-4-(N,N-dipropylaminocarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(oxybenzyl)ethylamino]-3-[2-cyano-4-(N,N-dipropylaminocarbonyl)phenoxy]-propan-2-ol;
N-[3-(3-chloro-2-cyano-4-dipropylsulfamoyl)phenoxy-2(R)-hydroxypropyl]-2-(4-methoxyphenyl)-1,1-dimethylethylamine;
N-[3-(2,3-dichloro-4-dipropylsulfamoyl)phenoxy-2(R)-hydroxypropyl]-2-(2,3-dichlorophenyl)-1,1-dimethylethylamine;
N-[3-(3-chloro-2-cyano-4-dimethylsulfamoyl)phenoxy-2(R)-hydroxypropyl]-2-(4-methoxyphenyl)-1,1-dimethylethylamine;
N-[3-(2,3-dichloro-4-morpholinosulfamyl)phenoxy-2(R)-hydroxypropyl]-2-(4-methoxyphenyl)-1,1-dimethylethylamine;
N-[3-(3-chloro-2-cyano-4-morpholinosulfamyl)phenoxy-2(R)-hydroxypropyl]-2-(4-methoxyphenyl)-1,1-dimethylethylamine;
N-[3-(3-chloro-2-cyano-4-pyrrolidinosulfamyl)phenoxy-2(R)-hydroxypropyl]-2-(4-methoxyphenyl)-1,1-dimethylethylamine;
N-[3-(3-chloro-2-cyano-4-pyrrolidinosulfamyl)phenoxy-2(R)-hydroxypropyl]-2-(2-naphthyl)-1,1-dimethylethylamine;
N-[3-(3-chloro-2-cyano-4-morpholinosulfamyl)phenoxy-2(R)-hydroxypropyl]-2-(2-naphthyl)-1,1-dimethylethylamine;
N-[3-(3-chloro-2-cyano-4-thiomorpholinosulfamyl)phenoxy-2(R)-hydroxypropyl]-2-(2-naphthyl)-1,1-dimethylethylamine;
N-[3-(3-chloro-2-cyano-4-thiomorpholinosulfamyl)phenoxy-2(R)-hydroxypropyl]-2-(4-methoxyphenyl)-1,1-dimethylethylamine;
N-[3-[3-chloro-2-cyano-4-(2′-cyanoeth-1-yl)-cyclopropylsulfamoyl]phenoxy-2(R)-hydroxypropyl]-2-(4-methoxyphenyl)-1,1-dimethylethylamine;
N-[3-[3-chloro-2-cyano-4-(2′-cyanoeth-1-yl)-cyclopropylsulfamoyl]phenoxy-2(R)-hydroxypropyl]-2-(2-napthyl)-1,1-dimethylethylamine;
N-[3-[3-chloro-2-cyano-4-(benzyl-cyclopropyl)sulfamoyl]phenoxy-2(R)-hydroxypropyl]-2-(2-napthyl)-1,1-dimethylethylamine;
N-[3-[3-chloro-2-cyano-4-(benzyl-cyclopropyl)sulfamoyl]phenoxy-2(R)-hydroxypropyl]-2-(4-methoxyphenyl)-1,1-dimethylethylamine;
N-[3-[3-chloro-2-cyano-4-(4′-N-t-butoxycarbonylpiperazino)sulfamyl]phenoxy-2(R)-hydroxypropyl]-2-(4-methoxyphenyl)-1,1-dimethylethylamine;
N-[3-[3-chloro-2-cyano-4-(4′-N-t-butoxycarbonylpiperazino)sulfamyl]phenoxy)-2(R)-hydroxypropyl]-2-(2-naphthyl)-1,1-dimethylethylamine;
N-[3-(2,3-dichloro-4-dipropysulfamoyl)phenoxy-2(R)-hydroxypropyl]-2-(2-naphthyl)-1,1-dimethylethylamine;
N-[3-(2,3-dichloro-4-pyrrolidinolsulfamoyl)phenoxy-2(R)-hydroxypropyl]-2-(4-methoxyphenyl)-1,1-dimethylethylamine;
N-[3-(2,3-dichloro-4-pyperidinolsulfamoyl)phenoxy-2(R)-hydroxypropyl]-2-(4-methoxyphenyl)-1,1-dimethylethylamine;
N-[3-(2,3-dichloro-4-cyclopropylsulfamoyl)phenoxy-2(R)-hydroxypropyl]-2-(4-methoxyphenyl)-1,1-dimethylethylamine;
N-[3-(2,3-dichloro-4-dipropylsulfamoyl)phenoxy-2(R)-hydroxypropyl]-2-(4-methoxyphenyl)-1,1-dimethylethylamine;
N-[3-(2,3-dichloro-4-propylsulfamoyl)phenoxy-2(R)-hydroxypropyl]-2-(4-methoxyphenyl)-1,1-dimethylethylamine;
N-[3-(2,3-dichloro-4-sulfamoyl)phenoxy-2(R)-hydroxypropyl]-2-(4-methoxyphenyl)-1,1-dimethylethylamine;
N-[3-(2,3-dichloro-4-methylsulfamoyl)phenoxy-2(R)-hydroxypropyl]-2-(4-methoxyphenyl)-1,1-dimethylethylamine;
N-[3-(3-chloro-2-cyano-4-pyrrolidinosulfamyl)phenoxy-2(R)-hydroxypropyl]-2-(4-fluorophenyl)-1,1-dimethylethylamine;
N-[3-(3-chloro-2-cyano-4-morphoinosulfamyl)phenoxy-2(R)-hydroxypropyl]-2-(benzyloxy)-1,1-dimethylethylamine;
N-[3-(2,3-dichloro-4-morpholinosulfamyl)phenoxy-2(R)-hydroxypropyl]-3-phenyl-1,1-dimethylpropylamine;
N-[3-(2,3-dichloro-4-morpholinosulfamyl)phenoxy-2(R)-hydroxypropyl]-4-phenyl-1,1-dimethylbutylamine;
or a pharmaceutically acceptable salt thereof.

66 more elements

Dependencies are inferred from the claim text.

Facts

Application: 09/402,310Filed 1 Oct 1999 · us provisional application
Priority: 8 Apr 1997
Granted: 25 Sep 2001
Term ends: Not estimatedThe source records don’t support an estimate.

Classification21 codes

C07D 295/192
Radicals derived from carboxylic acids: from aromatic carboxylic acids
A61P 1/02
Drugs for disorders of the alimentary tract or the digestive system: stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
A61P 3/14
For electrolyte homeostasis: for calcium homeostasis
A61P 5/18
Drugs for disorders of the endocrine system: of the parathyroid hormones

Family

Application60/042,724Us provisional application · filed 8 Apr 1997
Application60/061,327Us provisional application · filed 8 Oct 1997
Application60/061,329Us provisional application · filed 8 Oct 1997
Application60/061,330Us provisional application · filed 8 Oct 1997
Application60/061,333Us provisional application · filed 8 Oct 1997
Application60/061,331Us provisional application · filed 8 Oct 1997
US 6,294,531 B1This patent

From the US filing history. Foreign family members aren’t listed.

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Calcilytic compounds

AssigneeSmithKline Beecham Corporation

Life of this patent

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A compound selected from the group consisting of:

(R)-3-[2-cyano-4-[N-benzyl-N-[4-methylphenylsulfonyl]amino]phenoxy]-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-propan-2-ol;
(R)-3-[2-cyano-4-[N-[4-methylphenylsulfonyl]amino]phenoxy]-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-propan-2-ol;
(R)-3-[2-cyano-4-[N-methyl-N-[4-methylphenylsulfonyl]amino]phenoxy]-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-propan-2-ol;
(R)-3-[2-cyano-4-[N-methyl-N-[methylsulfonyl]amino]phenoxy]-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-propan-2-ol;
(R)-3-[2-cyano-4-[N-benzyl-N-[methylsulfonyl]amino]phenoxy]-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-propan-2-ol;
(R)-3-[2-cyano-4-[N-methylsulfonylamino]phenoxy]-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-propan-2-ol;
(R)-3-[2-cyano-4-[N-benzyl-N-[methylsulfonyl]amino]phenoxy]-1-[1,1-dimethyl-2-(2-naphthyl)ethylamino]-propan-2-ol;
(R)-3-[2-cyano-4-[N-[methylsulfonyl]amino]phenoxy]-1-[1,1-dimethyl-2-(2-naphthyl)ethylamino]-propan-2-ol;
(R)-3-[2-cyano-4-[N-benzyl-N-[4-methylphenylsulfonyl]amino]phenoxy]-1-[1,1-dimethyl-2-(2-naphthyl)ethylamino]-propan-2-ol;
(R)-3-[2-cyano-4-[N-benzyl-N-[4-methylphenylsulfonyl]amino]phenoxy]-1-[1,1-dimethyl-2-(benzyloxy)ethylamino]-propan-2-ol;
(R)-3-[2-cyano-4-[N-benzyl-N-[4-methylphenylsulfonyl]amino]phenoxy]-1-[1,1-dimethyl-3-phenylpropylamino]-propan-2-ol;
(R)-3-[2-cyano-4-[N-benzyl-N-[4-methylphenylsulfonyl]amino]phenoxy]-1-[1,1-dimethyl-4-phenylbutylamino]-propan-2-ol;
(R)-3-[2-cyano-4-[N-benzyl-N-ethylcarbonyl]phenoxy]-1-[1,1-dimethyl-2-(2-naphthyl)ethylamino]-propan-2-ol;
(R)-3-[2-cyano-4-[N-benzyl-N′-morpholino]ureido]phenoxy]-1-[1,1-dimethyl-2-(2-naphthyl)ethylamino]-propan-2-ol;
(R)-3-[2-cyano-4-[N-benzyl-N′-morpholino]ureido]phenoxy]-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-propan-2-ol;
(R)-3-[2-cyano-4-[N-methyl-N′-morpholino]ureido]phenoxy]-1-[1,1-dimethyl-2-(2-naphthyl)ethylamino]-propan-2-ol;
(R)-3-[2-cyano-4-[N-methyl-N′-morpholino]ureido]phenoxy]-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-3-[2-cyano-4-(N,N-dipropylaminocarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-3-[2-cyano-4-(N-propylaminocarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-3-[2-cyano-4-(N-piperidinylcarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-3-[2-cyano-4-(N-morpholinylcarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-3-[2,3-dichloro-4-(N-morpholinylcarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(2-naphthyl)ethylamino]-3-[2,3-dichloro-4-(N-morpholinylcarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-3-[2,3-dichloro-4-(N,N-dipropylaminocarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(2-naphthyl)ethylamino]-3-[2,3-dichloro-4-(N,N-dipropylaminocarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-3-[2-cyano, 3-chloro-4-(N-morpholinylcarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(2-naphthyl)ethylamino]-3-[2-cyano, 3-chloro-4-(N-morpholinylcarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-3-[2-cyano, 3-chloro-4-(N,N-dipropylaminocarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(2-naphthyl)ethylamino]-3-[2-cyano, 3-chloro-4-(N,N-dipropylaminocarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-3-[2-cyano-4-(N-pyrrolidinylcarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(4-methoxyphenyl)ethylamino]-3-[2-cyano-4-(N-piperazinylcarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(2-naphthyl)ethylamino]-3-[2-cyano-4-(N,N-dipropylaminocarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(2-naphthyl)ethylamino]-3-[2-cyano-4-(N-piperidinylcarbonyl)phenoxy3-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(2-naphthyl)ethylamino]-3-[2-cyano-4-(N-morpholinylcarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(2-naphthyl)ethylamino]-3-[2-cyano-4-(N-piperazinylcarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(2-naphthyl)ethylamino]-3-[2-cyano-4-(N-pyrrolidinylcarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-3-(phenyl)propylamino]-3-[2-cyano-4-(N,N-dipropylaminocarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-4-(phenyl)butylamino]-3-[2-cyano-4-(N,N-dipropylaminocarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-3-(phenoxy)propylamino]-3-[2-cyano-4-(N,N-dipropylaminocarbonyl)phenoxy]-propan-2-ol;
(R)-1-[1,1-dimethyl-2-(oxybenzyl)ethylamino]-3-[2-cyano-4-(N,N-dipropylaminocarbonyl)phenoxy]-propan-2-ol;
N-[3-(3-chloro-2-cyano-4-dipropylsulfamoyl)phenoxy-2(R)-hydroxypropyl]-2-(4-methoxyphenyl)-1,1-dimethylethylamine;
N-[3-(2,3-dichloro-4-dipropylsulfamoyl)phenoxy-2(R)-hydroxypropyl]-2-(2,3-dichlorophenyl)-1,1-dimethylethylamine;
N-[3-(3-chloro-2-cyano-4-dimethylsulfamoyl)phenoxy-2(R)-hydroxypropyl]-2-(4-methoxyphenyl)-1,1-dimethylethylamine;
N-[3-(2,3-dichloro-4-morpholinosulfamyl)phenoxy-2(R)-hydroxypropyl]-2-(4-methoxyphenyl)-1,1-dimethylethylamine;
N-[3-(3-chloro-2-cyano-4-morpholinosulfamyl)phenoxy-2(R)-hydroxypropyl]-2-(4-methoxyphenyl)-1,1-dimethylethylamine;
N-[3-(3-chloro-2-cyano-4-pyrrolidinosulfamyl)phenoxy-2(R)-hydroxypropyl]-2-(4-methoxyphenyl)-1,1-dimethylethylamine;
N-[3-(3-chloro-2-cyano-4-pyrrolidinosulfamyl)phenoxy-2(R)-hydroxypropyl]-2-(2-naphthyl)-1,1-dimethylethylamine;
N-[3-(3-chloro-2-cyano-4-morpholinosulfamyl)phenoxy-2(R)-hydroxypropyl]-2-(2-naphthyl)-1,1-dimethylethylamine;
N-[3-(3-chloro-2-cyano-4-thiomorpholinosulfamyl)phenoxy-2(R)-hydroxypropyl]-2-(2-naphthyl)-1,1-dimethylethylamine;
N-[3-(3-chloro-2-cyano-4-thiomorpholinosulfamyl)phenoxy-2(R)-hydroxypropyl]-2-(4-methoxyphenyl)-1,1-dimethylethylamine;
N-[3-[3-chloro-2-cyano-4-(2′-cyanoeth-1-yl)-cyclopropylsulfamoyl]phenoxy-2(R)-hydroxypropyl]-2-(4-methoxyphenyl)-1,1-dimethylethylamine;
N-[3-[3-chloro-2-cyano-4-(2′-cyanoeth-1-yl)-cyclopropylsulfamoyl]phenoxy-2(R)-hydroxypropyl]-2-(2-napthyl)-1,1-dimethylethylamine;
N-[3-[3-chloro-2-cyano-4-(benzyl-cyclopropyl)sulfamoyl]phenoxy-2(R)-hydroxypropyl]-2-(2-napthyl)-1,1-dimethylethylamine;
N-[3-[3-chloro-2-cyano-4-(benzyl-cyclopropyl)sulfamoyl]phenoxy-2(R)-hydroxypropyl]-2-(4-methoxyphenyl)-1,1-dimethylethylamine;
N-[3-[3-chloro-2-cyano-4-(4′-N-t-butoxycarbonylpiperazino)sulfamyl]phenoxy-2(R)-hydroxypropyl]-2-(4-methoxyphenyl)-1,1-dimethylethylamine;
N-[3-[3-chloro-2-cyano-4-(4′-N-t-butoxycarbonylpiperazino)sulfamyl]phenoxy)-2(R)-hydroxypropyl]-2-(2-naphthyl)-1,1-dimethylethylamine;
N-[3-(2,3-dichloro-4-dipropysulfamoyl)phenoxy-2(R)-hydroxypropyl]-2-(2-naphthyl)-1,1-dimethylethylamine;
N-[3-(2,3-dichloro-4-pyrrolidinolsulfamoyl)phenoxy-2(R)-hydroxypropyl]-2-(4-methoxyphenyl)-1,1-dimethylethylamine;
N-[3-(2,3-dichloro-4-pyperidinolsulfamoyl)phenoxy-2(R)-hydroxypropyl]-2-(4-methoxyphenyl)-1,1-dimethylethylamine;
N-[3-(2,3-dichloro-4-cyclopropylsulfamoyl)phenoxy-2(R)-hydroxypropyl]-2-(4-methoxyphenyl)-1,1-dimethylethylamine;
N-[3-(2,3-dichloro-4-dipropylsulfamoyl)phenoxy-2(R)-hydroxypropyl]-2-(4-methoxyphenyl)-1,1-dimethylethylamine;
N-[3-(2,3-dichloro-4-propylsulfamoyl)phenoxy-2(R)-hydroxypropyl]-2-(4-methoxyphenyl)-1,1-dimethylethylamine;
N-[3-(2,3-dichloro-4-sulfamoyl)phenoxy-2(R)-hydroxypropyl]-2-(4-methoxyphenyl)-1,1-dimethylethylamine;
N-[3-(2,3-dichloro-4-methylsulfamoyl)phenoxy-2(R)-hydroxypropyl]-2-(4-methoxyphenyl)-1,1-dimethylethylamine;
N-[3-(3-chloro-2-cyano-4-pyrrolidinosulfamyl)phenoxy-2(R)-hydroxypropyl]-2-(4-fluorophenyl)-1,1-dimethylethylamine;
N-[3-(3-chloro-2-cyano-4-morphoinosulfamyl)phenoxy-2(R)-hydroxypropyl]-2-(benzyloxy)-1,1-dimethylethylamine;
N-[3-(2,3-dichloro-4-morpholinosulfamyl)phenoxy-2(R)-hydroxypropyl]-3-phenyl-1,1-dimethylpropylamine;
N-[3-(2,3-dichloro-4-morpholinosulfamyl)phenoxy-2(R)-hydroxypropyl]-4-phenyl-1,1-dimethylbutylamine;
or a pharmaceutically acceptable salt thereof.

66 more elements

Facts

Application

09/402,310Filed 1 Oct 1999 · us provisional application

Priority

8 Apr 1997

Granted

25 Sep 2001

Term ends

Not estimatedThe source records don’t support an estimate.

Classification21 codes

C07D 295/192
Radicals derived from carboxylic acids: from aromatic carboxylic acids
A61P 1/02
Drugs for disorders of the alimentary tract or the digestive system: stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
A61P 3/14
For electrolyte homeostasis: for calcium homeostasis
A61P 5/18
Drugs for disorders of the endocrine system: of the parathyroid hormones

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Application60/042,724Us provisional application · filed 8 Apr 1997

Application60/061,327Us provisional application · filed 8 Oct 1997

Application60/061,329Us provisional application · filed 8 Oct 1997

Application60/061,330Us provisional application · filed 8 Oct 1997

Application60/061,333Us provisional application · filed 8 Oct 1997

Application60/061,331Us provisional application · filed 8 Oct 1997

US 6,294,531 B1This patent

From the US filing history. Foreign family members aren’t listed.