US 2025/0073233 A1Published application

MODULATORS OF RAR-RELATED ORPHAN RECEPTORS (RORs)

Assignee11949098 Canada Inc. (Nuredco)

InventorsAhmed Fouda, Jean I Tchervenkov, Steven Paraskevas, Sarita Negi

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Abstract

The invention encompasses the novel class of compounds represented by the Formula (I), (II), (III) and (IV) below, which are modulators of RORγt The invention also encompasses pharmaceutical compositions which include the compounds shown above and methods of treating or preventing autoimmune diseases and antibody mediated rejection.

Claims14

Dependent claims

A pharmaceutical compound selected from the group consisting of:

N-(3-(4-benzylpiperazine-1-carbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl)-2-fluorobenzamide;
N-(3-(benzylcarbamoyl)-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-5-chloro-2-(methylthio)pyrimidine-4-carboxamide;
N-(6-ethyl-3-{[(2-methylphenyl)amino]carbonyl}-4,5,6,7-tetrahydro-1-benzothien-2-yl)-1-methyl-1H-pyrazole-5-carboxamide;
N-{6-tert-butyl-3- [(4-methyl-1-piperazinyl)carbonyl]-4,5,6,7-tetrahydro-1-benzothien-2-yl}-2-fluorobenzamide;
2-fluoro-N-{6-methyl-3-[(4-methyl-1-piperazinyl)carbonyl]-4,5,6,7-tetrahydro-1-benzothien-2-yl}benzamide;
N-benzyl-2-[(trifluoroacetyl)amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide;
N-benzyl-2-({[(4-methyl-2-pyrimidinyl)thio]acetyl}amino)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide;
N-benzyl-2-[(1-piperidinylacetyl)amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide;
N-benzyl-2-{[(4-methyl-1-piperazinyl)acetyl]amino}-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide;
N-benzyl-2-{[(4-methyl-1-piperidinyl)acetyl]amino}-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide;
N-(3-(2-methylpyrrolidine-1-carbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl)nicotinamide;
N-(3-((2R,4R)-2,4-dimethylpiperidine-1-carbonyl)-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)nicotinamide;
N-(3-(((1r,4r)-4-hydroxycyclohexyl)carbamoyl)-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)nicotinamide;
N-(3-(3-ethylpyrrolidine-1-carbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl)nicotinamide;
N-benzyl-2-(2-((1-methyl-1H-imidazol-2-yl)thio)acetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide;
N-(3-(3-(hydroxymethyl) pyrrolidine-1-carbonyl)-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)nicotinamide;
N-(6,6-dimethyl-3-(morpholine-4-carbonyl)-4,5,6,7-tetrahydrobenzo[b] thiophen-2-yl)pyrazine-2-carboxamide;
N-(3-(((1-methyl-1H-1,2,4-triazol-3-yl)methyl)carbamoyl)-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)nicotinamide;
(S)-N-(3-((1-cyanoethyl)carbamoyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl)nicotinamide;
N-(3-((piperidin-4-ylmethyl)carbamoyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl)nicotinamide;
N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)pyrazine-2-carboxamide;
and
N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-5-methyl-2-(methylsulfonyl)pyrimidine-4-carboxamide;
and
a combination thereof.

22 more elements

Dependencies are inferred from the claim text.

Facts

Application: 18/953,335Filed 20 Nov 2024
Priority: 19 Nov 2018
Published: 6 Mar 2025
Term ends: Not estimatedThe source records don’t support an estimate.

Classification47 codes

A61K 31/498
Having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines: pyrazines or piperazines…
A61K 31/047
Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates: having two or more hydroxy groups, e.g. sorbitol
A61K 31/131
Amines: acyclic
A61K 31/17
Amides, e.g. hydroxamic acids: having the group >N—C—N< or >N—C—N<, e.g. urea, thiourea, carmustine

Family

Application62/769,167Us provisional application · filed 19 Nov 2018
Application62/769,849Us provisional application · filed 20 Nov 2018
Application17/294,915Continuation · filed 18 May 2021
Application18/953,335Continuation
US 12,390,461 B2Related patent
US 2022/0000864 A1Published application
US 2025/0073233 A1This patent

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

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Abstract

A pharmaceutical compound selected from the group consisting of:

N-(3-(4-benzylpiperazine-1-carbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl)-2-fluorobenzamide;
N-(3-(benzylcarbamoyl)-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-5-chloro-2-(methylthio)pyrimidine-4-carboxamide;
N-(6-ethyl-3-{[(2-methylphenyl)amino]carbonyl}-4,5,6,7-tetrahydro-1-benzothien-2-yl)-1-methyl-1H-pyrazole-5-carboxamide;
N-{6-tert-butyl-3- [(4-methyl-1-piperazinyl)carbonyl]-4,5,6,7-tetrahydro-1-benzothien-2-yl}-2-fluorobenzamide;
2-fluoro-N-{6-methyl-3-[(4-methyl-1-piperazinyl)carbonyl]-4,5,6,7-tetrahydro-1-benzothien-2-yl}benzamide;
N-benzyl-2-[(trifluoroacetyl)amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide;
N-benzyl-2-({[(4-methyl-2-pyrimidinyl)thio]acetyl}amino)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide;
N-benzyl-2-[(1-piperidinylacetyl)amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide;
N-benzyl-2-{[(4-methyl-1-piperazinyl)acetyl]amino}-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide;
N-benzyl-2-{[(4-methyl-1-piperidinyl)acetyl]amino}-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide;
N-(3-(2-methylpyrrolidine-1-carbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl)nicotinamide;
N-(3-((2R,4R)-2,4-dimethylpiperidine-1-carbonyl)-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)nicotinamide;
N-(3-(((1r,4r)-4-hydroxycyclohexyl)carbamoyl)-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)nicotinamide;
N-(3-(3-ethylpyrrolidine-1-carbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl)nicotinamide;
N-benzyl-2-(2-((1-methyl-1H-imidazol-2-yl)thio)acetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide;
N-(3-(3-(hydroxymethyl) pyrrolidine-1-carbonyl)-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)nicotinamide;
N-(6,6-dimethyl-3-(morpholine-4-carbonyl)-4,5,6,7-tetrahydrobenzo[b] thiophen-2-yl)pyrazine-2-carboxamide;
N-(3-(((1-methyl-1H-1,2,4-triazol-3-yl)methyl)carbamoyl)-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)nicotinamide;
(S)-N-(3-((1-cyanoethyl)carbamoyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl)nicotinamide;
N-(3-((piperidin-4-ylmethyl)carbamoyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl)nicotinamide;
N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)pyrazine-2-carboxamide;
and
N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-5-methyl-2-(methylsulfonyl)pyrimidine-4-carboxamide;
and
a combination thereof.

22 more elements

Facts

Application

18/953,335Filed 20 Nov 2024

Priority

19 Nov 2018

Published

6 Mar 2025

Term ends

Not estimatedThe source records don’t support an estimate.

Classification47 codes

A61K 31/498
Having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines: pyrazines or piperazines…
A61K 31/047
Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates: having two or more hydroxy groups, e.g. sorbitol
A61K 31/131
Amines: acyclic
A61K 31/17
Amides, e.g. hydroxamic acids: having the group >N—C—N< or >N—C—N<, e.g. urea, thiourea, carmustine

Family

Application62/769,167Us provisional application · filed 19 Nov 2018

Application62/769,849Us provisional application · filed 20 Nov 2018

Application17/294,915Continuation · filed 18 May 2021

Application18/953,335Continuation

US 12,390,461 B2Related patent

US 2022/0000864 A1Published application

US 2025/0073233 A1This patent

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