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5-hydroxy-7-oxabicyclo[2.2.1]heptane-2-carboxamide derivatives for inducing chondrogenesis for treating joint damage

A haloalkyl, phenyl technology, applied in the direction of heterocyclic compound active ingredients, drug combinations, bone diseases, etc., can solve the problems of limited repair ability and deterioration of articular cartilage

Pending Publication Date: 2021-06-22
NOVARTIS AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the limited ability of articular cartilage to repair, even small undetectable damage often deteriorates over time and leads to OA

Method used

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  • 5-hydroxy-7-oxabicyclo[2.2.1]heptane-2-carboxamide derivatives for inducing chondrogenesis for treating joint damage
  • 5-hydroxy-7-oxabicyclo[2.2.1]heptane-2-carboxamide derivatives for inducing chondrogenesis for treating joint damage
  • 5-hydroxy-7-oxabicyclo[2.2.1]heptane-2-carboxamide derivatives for inducing chondrogenesis for treating joint damage

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Example 1. A compound of formula (1 ) or an enantiomer, mixture of enantiomers, or a pharmaceutically acceptable salt thereof, as described above.

Embodiment 2

[0051] Embodiment 2. The compound having formula (1) or its enantiomer, enantiomer mixture or pharmaceutically acceptable salt thereof according to embodiment 1; wherein R 2 is phenyl, pyrazolyl, pyridyl or pyrimidyl; said phenyl, pyrazolyl, pyridyl or pyrimidyl are each independently selected from halogen, C by 1-2 1-6 Alkyl, C 1-6 Haloalkyl or C 1-6 Alkoxy substituents are substituted.

Embodiment 3

[0052] Embodiment 3. The compound having formula (1) or its enantiomer, enantiomer mixture or pharmaceutically acceptable salt thereof according to embodiment 1; wherein R 2 selected from phenyl, pyrazolyl or pyrimidinyl; each of said phenyl, pyrazolyl or pyrimidinyl is independently selected from halo, C 1-6 Alkyl, C 1-6 Haloalkyl or C 1-6 Alkoxy substituent substitution; or R 2 is halogenated, C 1-6 Haloalkyl or C 1-6 Alkoxy substituted pyridyl.

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PUM

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Abstract

The present invention provides 5-hydroxy-7- oxabicyclo[2.2.1]heptane-2-carboxamide derivatives of Formula (1), wherein the variables are as defined herein. The present invention further provides pharmaceutical compositions comprising such compounds. The compounds are used for inducing chondrogenesis, in methods of treating or preventing joint damage, resulting from joint injury or arthritis, and for inducing hyaline cartilage production. The present description discloses the preparation of exemplary compounds as well as pharmacological data thereof (examples 1 to 89; tables 1 and 2). An exemplary compound is e.g. rac-(1R,2R,3S,4R,5S)-N-(2-fluoro-5- (trifluoromethyl)phenyl)-5-hydroxy-3-(3-(trifluoromethyl)phenyl)-7- oxabicyclo[2.2.1]heptane-2-carboxamid (example 1).

Description

[0001] Cross References to Related Applications [0002] This application claims the benefit of U.S. Provisional Application Serial No. 62 / 776,267, filed December 6, 2018, which is hereby incorporated by reference in its entirety. technical field [0003] The present invention relates to compositions and methods for treating or preventing joint damage resulting from joint damage and arthritis or for cartilage repair. Background technique [0004] Osteoarthritis (OA) represents the most common musculoskeletal disorder. Approximately 40 million Americans are currently affected, and due to an aging population and increasing life expectancy, this number is expected to increase to 60 million within the next two decades, making osteoarthritis the fourth leading cause of disability. OA is characterized by the slow degenerative destruction of the joints, which include the articular cartilage (containing cells and matrix that provide lubrication and cushioning for the joint) and the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/08A61K31/34A61K31/443A61K31/5377A61K31/4155A61K31/506A61P19/02
CPCC07D493/08A61P19/02A61K31/343A61K31/443A61K45/06
Inventor J·P·拉伊内斯A·瓦利尔
Owner NOVARTIS AG