US 11,773,058 B2Granted

Sulfonamide carboxamide compounds

AssigneeInflazome Limited

InventorsDavid Miller, Angus MacLeod, Jimmy Van Wiltenburg, Stephen Thom, Stephen St-Gallay, Jonathan Shannon

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Abstract

The present invention relates to compounds of formula (I): Formula (I) wherein Q is selected from O or S; L is a saturated or unsaturated, optionally substituted C1-C12 hydrocarbylene group optionally including one or more heteroatoms N, O or S; R1 is —NR3R4, —OR5, —(C═NR6)R7, —(CO)R8, —CN, —N3, a quaternary ammonium group or an optionally substituted heterocycle; R3, R4, R5, R6, R7 and R8 are each independently hydrogen or a saturated or unsaturated, optionally substituted C1-C10 hydrocarbyl group optionally including one or more heteroatoms N, O or S; wherein optionally L and R3, or L and R4, or R3 and R4, or L and R5, or L and R6, or L and R7, or R6 and R7, or L and R8 together with the atom(s) to which they are attached may form a 3- to 12-membered, saturated or unsaturated, optionally substituted cyclic group; and R2 is a cyclic group substituted at the a-position, wherein R2 may optionally be further substituted; provided that the atom of L which is attached to the sulfur atom of the sulfonylurea group is a carbon atom and is not a ring atom of a heterocyclic or aromatic group. The present invention further relates to salts, solvates and prodrugs of such compounds, to pharmaceutical compositions comprising such compounds, and to the use of such compounds in the treatment and prevention of medical disorders and diseases, most especially by the inhibition of NLRP3.

Claims20

Dependent claims

A compound of formula (I):

or a pharmaceutically acceptable salt or solvate thereof, wherein:
Q is O;
L is a C1-C12 hydrocarbylene group which is saturated or a combination of saturated and aromatic, wherein the hydrocarbylene group may be straight-chained or branched, or include cyclic groups, wherein the hydrocarbylene group may optionally be substituted, and wherein the hydrocarbylene group may optionally include one or more heteroatoms N, O or S in its carbon skeleton;
R1 is —NR3R4, —OR5, —C(═NR6)R7, —(CO)R8, —CN, —N3, a quaternary ammonium group and its counterion, or an optionally substituted heterocycle;
R3, R4, R5, R6, R7 and R8 are each independently hydrogen or a saturated or unsaturated C1-C10 hydrocarbyl group, wherein the hydrocarbyl group may be straight-chained or branched, or be or include cyclic groups, wherein the hydrocarbyl group may optionally be substituted, and wherein the hydrocarbyl group may optionally include one or more heteroatoms N, O or S in its carbon skeleton;
or L and R3, or L and R4, or R3 and R4 together with the nitrogen atom to which they are attached form a 3- to 12-membered saturated or unsaturated cyclic group, wherein the cyclic group may optionally be substituted;
or L and R5 together with the oxygen atom to which they are attached form a 3- to 12-membered saturated or unsaturated cyclic group, wherein the cyclic group may optionally be substituted;
or L and R6, or L and R7, or R6 and R7 together with the —(C═N)— group to which they are attached form a 3- to 12-membered saturated or unsaturated cyclic group, wherein the cyclic group may optionally be substituted;
or L and R8 together with the —(C═O)— group to which they are attached form a 3- to 12-membered saturated or unsaturated cyclic group, wherein the cyclic group may optionally be substituted;
and
R2 is a cyclic group substituted at the α and α′ positions, wherein R2 may optionally be further substituted;
provided that the atom of L which is attached to the sulfur atom of the sulfonylurea group is a carbon atom and is not a ring atom of any cyclic group;
and
provided that the compound of formula (I) is not

11 more elements

A prodrug of a compound of formula (I):

or a pharmaceutically acceptable salt or solvate thereof, wherein:
Q is O;
L is a C1-C12 hydrocarbylene group which is saturated or aromatic or a combination thereof, wherein the hydrocarbylene group may be straight-chained or branched, or include cyclic groups, wherein the hydrocarbylene group may optionally be substituted, and wherein the hydrocarbylene group may optionally include one or more heteroatoms N, O or S in its carbon skeleton;
R1 is —NR3R4, —OR5, —C(═NR6)R7, —(CO)R8, —CN, —N3, a quaternary ammonium group and its counterion, or an optionally substituted heterocycle;
R3, R4, R5, R6, R7 and R8 are each independently hydrogen or a saturated or unsaturated C1-C10 hydrocarbyl group, wherein the hydrocarbyl group may be straight-chained or branched, or be or include cyclic groups, wherein the hydrocarbyl group may optionally be substituted, and wherein the hydrocarbyl group may optionally include one or more heteroatoms N, O or S in its carbon skeleton;
or L and R3, or L and R4, or R3 and R4 together with the nitrogen atom to which they are attached form a 3- to 12-membered saturated or unsaturated cyclic group, wherein the cyclic group may optionally be substituted;
or L and R5 together with the oxygen atom to which they are attached form a 3- to 12-membered saturated or unsaturated cyclic group, wherein the cyclic group may optionally be substituted;
or L and R6, or L and R7, or R6 and R7 together with the —(C═N)— group to which they are attached form a 3- to 12-membered saturated or unsaturated cyclic group, wherein the cyclic group may optionally be substituted;
or L and R8 together with the —(C═O)— group to which they are attached form a 3- to 12-membered saturated or unsaturated cyclic group, wherein the cyclic group may optionally be substituted;
and
R2 is a cyclic group substituted at the α and α′ positions, wherein R2 may optionally be further substituted;
provided that the atom of L which is attached to the sulfur atom of the sulfonylurea group is a carbon atom and is not a ring atom of any cyclic group;
and
provided that the compound of formula (I) is not

11 more elements

Dependencies are inferred from the claim text.

Facts

Application: 16/638,646Filed 15 Aug 2018
Priority: GB 171307915 Aug 2017
Published: US 2020/0331850 A122 Oct 2020
Granted: 3 Oct 2023
Term ends: Not estimatedThe source records don’t support an estimate.

Classification32 codes

C07C 311/55
Either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea: having sulfur atoms of the sulfonylurea groups bound to acyclic carbon atoms
C07D 213/643
Attached in position 2 or 6: 2-Phenoxypyridines; Derivatives thereof
C07C 311/58
Having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings: having nitrogen atoms of the sulfonylurea…
C07D 205/04
Not condensed with other rings: having no double bonds between ring members or between ring members and non-ring members