IP Library › Granted Patent US 11,117,903
Granted Patent B2
US 11,117,903 · App. 16/722,592 · Granted Sep 14, 2021

Pyridine derivatives

Inventors: Beat Frei (Basel, CH); Luca Gobbi (Basel, CH); Uwe Grether (Basel, CH); Fabienne Ricklin (Basel, CH); Stephan Roever (Basel, CH); Mark Rogers-Evans (Basel, CH); Didier Rombach (Basel, CH)
Assignee: Hoffmann-La Roche Inc.
C07D491/107A61K9/2013A61K9/2027A61K9/2054A61K9/2059A61K9/2813A61K9/2866A61K9/485A61K9/4858A61K9/4866A61K47/12A61K47/34C07D213/81C07D401/12C07D405/12C07D413/04C07D413/14
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Quick Facts
Patent No.
US 11,117,903
App. No.
16/722,592
Granted
Sep 14, 2021
Kind
B2
Abstract

The invention relates to compound of formula (I) wherein R 1 to R 3 are as defined in the description and in the claims. The compound of formula (I) can be used as a medicament.

Claims (34)

1. A compound selected from the group consisting of:

5-(cyclopropylmethoxy)-4-(2,4-dichlorophenyl)-N-[(2S)-1-hydroxy-4-methylpentan-2-yl]pyridine-2-carboxamide;

4-(4-chlorophenyl)-5-(cyclopropylmethoxy)-N-[(1R,2S)-2-hydroxycyclohexyl]pyridine-2-carboxamide;

4-(4-chlorophenyl)-5-(cyclopropylmethoxy)-N-[(1S,2R)-2-hydroxycyclohexyl]pyridine-2-carboxamide;

methyl 2-[[4-(4-chlorophenyl)-5-(cyclopropylmethoxy)pyridine-2-carbonyl]amino]-2-ethylbutanoate;

methyl 2-[[5-(cyclopropylmethoxy)-4-(3,4-dichlorophenyl)pyridine-2-carbonyl]amino]-2-ethylbutanoate;

4-(4-chlorophenyl)-5-(cyclopropylmethoxy)-N-[(1R,2S)-2-methoxycyclohexyl]pyridine-2-carboxamide;

5-chloro-4-(cyclopropylmethoxy)-N-[(1R)-2-hydroxy-1-phenylethyl]pyridine-2-carboxamide;

5-chloro-4-(cyclopropylmethoxy)-N-[(2S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]pyridine-2-carboxamide;

5-chloro-4-(cyclopropylmethoxy)-N-[(2S)-4-methyl-1-(methylamino)-1-oxopentan-2-yl]pyridine-2-carboxamide;

5-chloro-4-(cyclopropylmethoxy)-N-[(2R)-4-methyl-1-(methylamino)-1-oxopentan-2-yl]pyridine-2-carboxamide;

5-cyclopropyl-N-[(2S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]-4-[(3-methyloxetan-3-yl)methoxy]pyridine-2-carboxamide;

6-[6-(5-tert-butyl-1,2,4-oxadiazol-3-yl)-4-(cyclopropylmethoxy)pyri din-3-yl]-2-oxa-6-azaspiro [3 0.3]heptane;

tert-butyl (2S)-24[2-(5-tert-butyl-1,2,4-oxadiazol-3-yl)-5-cyclopropylpyridin-4-yl]oxymethyl]pyrrolidine-1-carboxylate;

tert-butyl (3R)-3-[2-(5-tert-butyl-1,2,4-oxadiazol-3-yl)-5-cyclopropylpyridin-4-yl]oxypyrrolidine-1-carboxylate;

5-tert-butyl-3-[5-cyclopropyl-4-[(3-methylsulfonylphenyl)methoxy]pyridin-2-yl]-1,2,4-oxadiazole;

N-[1-(azetidin-3-yl)-1-(5-methyl-1,3,4-oxadiazol-2-yl)ethyl]-5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridine-2-carboxamide;

ethyl 2-[[5-cyclopropyl-4-[(3-methyloxetan-3-yl)methoxy]pyridine-2-carbonyl]amino]-2-ethylbutanoate;

5-chloro-N-[1-cyclopropyl-2-(5-methyl-1,2,4-oxadiazol-3-yl)propan-2-yl]-4-[(2,2-difluoro-1-methylcyclopropyl)methoxy]pyridine-2-carboxamide;

4-(benzotriazol-1-yloxy)-N-[1-cyclopropyl-2-(5-methyl-1,2,4-oxadiazol-3-yl)propan-2-yl]-5-(trifluoromethyl)pyridine-2-carboxamide;

N-(4-amino-2-cyclopropyl-4-oxobutan-2-yl)-5-cyclopropyl-4-[(5-fluoropyridin-2-yl)methoxy]pyridine-2-carboxamide; and

N-[(2S)-1-cyclopropyl-2-(5-methyl-1,2,4-oxadiazol 01-3-yl)propan-2-yl]-4-(6-fluoropyridin-3-yl)-5-phenylmethoxypyridine-2-carboxamide;

or a pharmaceutically acceptable salt thereof.

2. A compound selected from the group consisting of:

5-(cyclopropylmethoxy)-4-(2,4-dichlorophenyl)-N-[(2S)-1-hydroxy-4-methylpentan-2-yl]pyridine-2-carboxamide;

methyl 2-[[5-(cyclopropylmethoxy)-4-(3,4-dichlorophenyl)pyridine-2-carbonyl]amino]-2-ethylbutanoate;

5-chloro-4-(cyclopropylmethoxy)-N-[(2S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]pyridine-2-carboxamide;

5-cyclopropyl-N-[(2S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]-4-[(3-methyloxetan-3-yl)methoxy]pyridine-2-carboxamide; and

N-(4-amino-2-cyclopropyl-4-oxobutan-2-yl)-5-cyclopropyl-4-[(5-fluoropyridin-2-yl)methoxy]pyridine-2-carboxamide;

or a pharmaceutically acceptable salt thereof.

3. A pharmaceutical composition comprising a compound in accordance with claim 1 , or a pharmaceutically acceptable salt thereof, and a therapeutically inert carrier.

4. A method for the treatment of pain, neuropathic pain, asthma, osteoporosis, inflammation, psychiatric diseases, psychosis, oncology, encephalitis, malaria, allergy, immunological disorders, arthritis, gastrointestinal disorders, psychiatric disorders rheumatoid arthritis, psychosis or allergy, which method comprises administering an effective amount of a compound of claim 1 , or a pharmaceutically acceptable salt thereof, to a patient in need thereof.

5. A pharmaceutical composition comprising a compound in accordance with claim 2 , or a pharmaceutically acceptable salt thereof, and a therapeutically inert carrier.

6. A method for the treatment of pain, neuropathic pain, asthma, osteoporosis, inflammation, psychiatric diseases, psychosis, oncology, encephalitis, malaria, allergy, immunological disorders, arthritis, gastrointestinal disorders, psychiatric disorders rheumatoid arthritis, psychosis or allergy, which method comprises administering an effective amount of a compound of claim 2 , or a pharmaceutically acceptable salt thereof, to a patient in need thereof.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 5, 2020
From: GOBBI, LUCA; ROMBACH, DIDIER; RICKLIN, FABIENNE; FREI, BEAT; GRETHER, UWE; ROEVER, STEPHAN; ROGERS-EVANS, MARK
To: F. HOFFMANN-LA ROCHE AG
Reel/Frame 051730/0359 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 5, 2020
From: F. HOFFMANN-LA ROCHE AG
To: HOFFMANN-LA ROCHE INC.
Reel/Frame 051730/0374 →
Priority Claims (1)
EP 17176884 · Jun 20, 2017 · regional
Continuity (2)
Continuation PCTEP2018066207 · Jun 19, 2018
Related Publication 20200239490A1 · Jul 30, 2020