US 10,308,659 B2Granted

Pyridine derivatives

AssigneeHoffmann-La Roche Inc.

InventorsOlivier Gavelle, Uwe Grether, Atsushi Kimbara, Matthias Nettekoven, Roever Stephan, Mark Rogers-Evans, Didier Rombach, Tanja Schulz-Gasch

Life of this patent

Estimating the term…

Abstract

The invention relates to a compound of formula (I) wherein A and R1 to R4 are defined as in the description and in the claims. The compound of formula (I) can be used as a medicament.

Claims10

Dependent claims

A compound selected from the group consisting of:

5-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-3-methyl-1,2,4-oxadiazole;
5[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-3-phenyl-1,2,4-oxadiazole;
3-cyclopropyl-5-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
3-cyclopentyl-5-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
3-benzyl-5-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]1,2,4-oxadiazole;
3-tert-butyl-5-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
3-cyclopropyl-5-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-3-(trifluoromethyl)-1,2,4-oxadiazole;
5-cyclopropyl-3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-5-(methoxymethyl)-1,2,4-oxadiazole;
3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-5-ethyl-1,2,4-oxadiazole;
3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-5-propan-2-yl-1,2,4-oxadiazole;
[3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-1,2,4-oxadiazol-5-yl]methanol;
3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-5-(trifluoromethyl)-1,2,4-oxadiazole;
1-[3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-1,2,4-oxadiazol-5-yl]cyclopropan-1-ol;
3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-5-(1-methylcyclopropyl)-1,2,4-oxadiazole;
1-[3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-1,2,4-oxadiazol-5-yl]cyclopropane-1-carboxamide;
2-[3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-1,2,4-oxadiazol-5-yl]propan-2-ol;
5-tert-butyl-3-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
3-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-5-(1-methylcyclopropyl)-1,2,4-oxadiazole;
3-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-5-propan-2-yl-1,2,4-oxadiazole;
1-[3-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazol-5-yl]cyclopropan-1-ol;
3-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
3-tert-butyl-5-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-3 -propan-2-yl-1,2,4-oxadiazole;
5-tert-butyl-3-[4-(cyclopropylmethoxy)-5-methylsulfonylpyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxypyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-[(2R)-1,1,1-trifluoropropan-2-yl]oxypyridin-2-yl]-1,2,4-oxadiazole;
3-tert-butyl-5-[5-cyclopropyl-4-[(2R)-1,1,1-trifluoropropan-2-yl]oxypyridin-2-yl]-1,2,4-oxadiazole;
3-tert-butyl-5-[5-cyclopropyl-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxypyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3[5-cyclopropyl-4-[(4-fluorophenyl)methoxy]pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-[(3-methyloxetan-3-yl)methoxy]pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(oxolan-2-ylmethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-[[(2S)-1-methylpyrrolidin-2-yl]methoxy]pyridin -2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(oxetan-2-ylmethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(4-fluorophenoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-methylsulfonyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-chloro-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
3-[5-chloro-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-5-cyclopropyl-1,2,4-oxadiazole;
5-cyclopropyl-3-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(4-methylsulfonylphenoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-(5-cyclopropyl-4-cyclopropylsulfonylpyridin-2-yl)-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(2-ethoxyethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(1-methoxybutan-2-yloxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3[5-cyclopropyl-4-[2-[(2-methylpropan-2-yl)oxy]ethoxy]pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-[1-[(2-methylpropan-2-yl)oxy]propan-2-yloxy]pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5cyclopropyl-4-(1-methoxypropan-2-yloxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(3-methoxybutoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(oxetan-3-ylmethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-cyclopropyl-3-[5-cyclopropyl-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxypyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(2-pyrrolidin-l-ylethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(2-piperidin-l-ylethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(1-piperidin-1-ylpropan-2-yloxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-[(1-methylpiperidin-2-yl)methoxy]pyridin-2-yl]-1,2,4-oxadiazole;
2-[2-(5-tert-butyl-1,2,4-oxadiazol-3-yl)-5-cyclopropylpyridin-4-yl]oxy-N,N-diethylpropan-1-amine;
3-[[2-(5-tert-butyl-1,2,4-oxadiazol-3-yl)-5-cyclopropylpyridin-4-yl]oxyethyl]morpholine;
4-[2-[2-(5-tert-butyl-1,2,4-oxadiazol-3-yl)-5-cyclopropylpyridin-4-yl]oxyethyl]morpholine;
5-tert-butyl-3-[5-cyclopropyl-4-[(3-fluorooxetan-3-yl)methoxy]pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-[(2,5-dimethyl-1,3-oxazol-4-yl)methoxy]pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-[(5-methyl-1,2-oxazol-3-yl)methoxy]pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(3-methylsulfonylphenoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-(6-chloro-5-cyclopropyl-4-(4-fluorobenzyloxy)pyridin-2-yl)-1,2,4-oxadiazole;
2-tert-butyl-5-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,3,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(2,2-difluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(2-fluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(pyridin-2-ylmethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-[(5-fluoropyridin-2-yl)methoxy]pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(pyridin-3-ylmethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
2-tert-butyl-5-[5-cyclopropyl-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxypyridin-2-yl]-1,3,4-oxadiazole;
3-tert-butyl-5-[5-cyclopropyl-4-[[(2S)-1-methylpyrrolidin-2-yl]methoxy]pyridin-2-yl]-1,2,4-oxadiazole;
and
3-tert-butyl-5-(5-cyclopropyl-4-(2,2-difluoroethoxy)pyridin-2-yl)-1,2,4-oxadiazole;
or a pharmaceutically acceptable salt thereof.

71 more elements

A compound selected from the group consisting of:

5-tert-butyl-3-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
3 -tert-butyl-5-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-[(3-methyloxetan-3-yl)methoxy]pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(oxolan-2-ylmethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(4-fluorophenoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(2-ethoxyethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(3-methoxybutoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(oxetan-3-ylmethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-[(5-fluoropyridin-2-yl)methoxy]pyridin-2-yl]-1,2,4-oxadiazole;
3-tert-butyl-5-(5-cyclopropyl-4-(2,2-difluoroethoxy)pyridin-2-yl)-1,2,4-oxadiazole;
or a pharmaceutically acceptable salt thereof.

8 more elements

Dependencies are inferred from the claim text.

Facts

Application: 14/868,305Filed 28 Sep 2015 · continuation
Priority: EP 1316117626 Mar 2013
Published: US 2016/0016968 A121 Jan 2016
Granted: 4 Jun 2019
Term ends: Not estimatedThe source records don’t support an estimate.

Classification31 codes

C07D 491/107
Spiro-condensed systems: with only one oxygen atom as ring hetero atom in the oxygen-containing ring
A61P 1/02
Drugs for disorders of the alimentary tract or the digestive system: stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
A61P 1/04
Drugs for disorders of the alimentary tract or the digestive system: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of…
A61P 1/16
Drugs for disorders of the alimentary tract or the digestive system: for liver or gallbladder disorders, e.g. hepatoprotective agents,…

Family

PCT/EP2014/055797Parent of this continuation · filed 24 Mar 2014
US 2016/0016968 A1Pre-grant publication · published 21 Jan 2016
US 10,308,659 B2This patent

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

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Abstract

The invention relates to a compound of formula (I) wherein A and R1 to R4 are defined as in the description and in the claims. The compound of formula (I) can be used as a medicament.

A compound selected from the group consisting of:

5-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-3-methyl-1,2,4-oxadiazole;
5[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-3-phenyl-1,2,4-oxadiazole;
3-cyclopropyl-5-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
3-cyclopentyl-5-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
3-benzyl-5-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]1,2,4-oxadiazole;
3-tert-butyl-5-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
3-cyclopropyl-5-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-3-(trifluoromethyl)-1,2,4-oxadiazole;
5-cyclopropyl-3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-5-(methoxymethyl)-1,2,4-oxadiazole;
3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-5-ethyl-1,2,4-oxadiazole;
3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-5-propan-2-yl-1,2,4-oxadiazole;
[3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-1,2,4-oxadiazol-5-yl]methanol;
3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-5-(trifluoromethyl)-1,2,4-oxadiazole;
1-[3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-1,2,4-oxadiazol-5-yl]cyclopropan-1-ol;
3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-5-(1-methylcyclopropyl)-1,2,4-oxadiazole;
1-[3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-1,2,4-oxadiazol-5-yl]cyclopropane-1-carboxamide;
2-[3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-1,2,4-oxadiazol-5-yl]propan-2-ol;
5-tert-butyl-3-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
3-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-5-(1-methylcyclopropyl)-1,2,4-oxadiazole;
3-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-5-propan-2-yl-1,2,4-oxadiazole;
1-[3-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazol-5-yl]cyclopropan-1-ol;
3-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
3-tert-butyl-5-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-3 -propan-2-yl-1,2,4-oxadiazole;
5-tert-butyl-3-[4-(cyclopropylmethoxy)-5-methylsulfonylpyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxypyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-[(2R)-1,1,1-trifluoropropan-2-yl]oxypyridin-2-yl]-1,2,4-oxadiazole;
3-tert-butyl-5-[5-cyclopropyl-4-[(2R)-1,1,1-trifluoropropan-2-yl]oxypyridin-2-yl]-1,2,4-oxadiazole;
3-tert-butyl-5-[5-cyclopropyl-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxypyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3[5-cyclopropyl-4-[(4-fluorophenyl)methoxy]pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-[(3-methyloxetan-3-yl)methoxy]pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(oxolan-2-ylmethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-[[(2S)-1-methylpyrrolidin-2-yl]methoxy]pyridin -2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(oxetan-2-ylmethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(4-fluorophenoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-methylsulfonyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-chloro-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
3-[5-chloro-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-5-cyclopropyl-1,2,4-oxadiazole;
5-cyclopropyl-3-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(4-methylsulfonylphenoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-(5-cyclopropyl-4-cyclopropylsulfonylpyridin-2-yl)-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(2-ethoxyethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(1-methoxybutan-2-yloxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3[5-cyclopropyl-4-[2-[(2-methylpropan-2-yl)oxy]ethoxy]pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-[1-[(2-methylpropan-2-yl)oxy]propan-2-yloxy]pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5cyclopropyl-4-(1-methoxypropan-2-yloxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(3-methoxybutoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(oxetan-3-ylmethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-cyclopropyl-3-[5-cyclopropyl-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxypyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(2-pyrrolidin-l-ylethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(2-piperidin-l-ylethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(1-piperidin-1-ylpropan-2-yloxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-[(1-methylpiperidin-2-yl)methoxy]pyridin-2-yl]-1,2,4-oxadiazole;
2-[2-(5-tert-butyl-1,2,4-oxadiazol-3-yl)-5-cyclopropylpyridin-4-yl]oxy-N,N-diethylpropan-1-amine;
3-[[2-(5-tert-butyl-1,2,4-oxadiazol-3-yl)-5-cyclopropylpyridin-4-yl]oxyethyl]morpholine;
4-[2-[2-(5-tert-butyl-1,2,4-oxadiazol-3-yl)-5-cyclopropylpyridin-4-yl]oxyethyl]morpholine;
5-tert-butyl-3-[5-cyclopropyl-4-[(3-fluorooxetan-3-yl)methoxy]pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-[(2,5-dimethyl-1,3-oxazol-4-yl)methoxy]pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-[(5-methyl-1,2-oxazol-3-yl)methoxy]pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(3-methylsulfonylphenoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-(6-chloro-5-cyclopropyl-4-(4-fluorobenzyloxy)pyridin-2-yl)-1,2,4-oxadiazole;
2-tert-butyl-5-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,3,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(2,2-difluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(2-fluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(pyridin-2-ylmethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-[(5-fluoropyridin-2-yl)methoxy]pyridin-2-yl]-1,2,4-oxadiazole;
5-tert-butyl-3-[5-cyclopropyl-4-(pyridin-3-ylmethoxy)pyridin-2-yl]-1,2,4-oxadiazole;
2-tert-butyl-5-[5-cyclopropyl-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxypyridin-2-yl]-1,3,4-oxadiazole;
3-tert-butyl-5-[5-cyclopropyl-4-[[(2S)-1-methylpyrrolidin-2-yl]methoxy]pyridin-2-yl]-1,2,4-oxadiazole;
and
3-tert-butyl-5-(5-cyclopropyl-4-(2,2-difluoroethoxy)pyridin-2-yl)-1,2,4-oxadiazole;
or a pharmaceutically acceptable salt thereof.

71 more elements

Facts

Application

14/868,305Filed 28 Sep 2015 · continuation

Priority

EP 1316117626 Mar 2013

Published

US 2016/0016968 A121 Jan 2016

Granted

4 Jun 2019

Term ends

Not estimatedThe source records don’t support an estimate.

Classification31 codes

C07D 491/107
Spiro-condensed systems: with only one oxygen atom as ring hetero atom in the oxygen-containing ring
A61P 1/02
Drugs for disorders of the alimentary tract or the digestive system: stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
A61P 1/04
Drugs for disorders of the alimentary tract or the digestive system: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of…
A61P 1/16
Drugs for disorders of the alimentary tract or the digestive system: for liver or gallbladder disorders, e.g. hepatoprotective agents,…