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US RE47,415 E1Granted
Pyrimidinecarboxamides as CXCR2 modulators
AssigneeSyntrix Biosystems, Inc.
InventorsDean Y. Maeda, John A. Zebala
Life of this patent
Estimating the term…
Abstract
There is disclosed pyridine- and pyrimidinecarboxamide compounds useful as pharmaceutical agents, synthesis processes, and pharmaceutical compositions which include pyridine- and pyrimidinecarboxamides compounds. More specifically, there is disclosed a genus of CXCR2 inhibitor compounds that are useful for treating a variety of inflammatory and neoplastic disorders.
Claims62
A compound comprising a compound from of formula (1):
- wherein R1 and R2 are independently is selected from hydrogen, 2- or 3- or 4-halo-phenyl, heteroalkyl, alkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, or and heterocyclylalkyl;
- wherein R2 is selected from 2- or 3- or 4-halo-phenyl, heteroalkyl, alkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, and heterocyclylalkyl;
- wherein R3 is selected from —B(R4R5), —R6—B(R4R5), alkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocyclyl and, heterocyclylalkyl, R6, —O—R6, —S(O)y—R6 (wherein y=0, 1, or 2), wherein y is 0, 1, or 2, —P(O)—(R4R5), —N(R7R8), or C(O)—R9 —C(O)—R9, and alkyl, wherein alkyl is unsubstituted or substituted with one or more substituents selected from hydroxy, amino, alkylamino, boronyl, nitro, and cyano;
- wherein R6 is selected from alkyl, aryl, arylalkyl, cycloalkyl with 5 to 7 ring atoms, heteroaryl, heteroarylalkyl, heterocyclyl or and heterocyclylalkyl;
- wherein R4 and R5 are independently selected from hydrogen, hydroxyl, aryloxy, or alkoxy, or wherein R4 and R5 together form a cyclic ester, or an acid anhydride (either mixed or symmetrical), wherein the acid anyhydride is either mixed or symmetrical;
- wherein R7 and R8 are independently selected from hydrogen, alkyl, haloalkyl, aryl, cycloalkyl, arylalkyl, heteroalkyl, heterocyclyl or, and heterocyclylalkyl;
- R7 and R8 are both oxygen to form a nitro group;
- or R7 and R8 together with the nitrogen to which they are attached, form a heterocyclyl;
- wherein R9 is selected from an alkyl consisting of 1 or 3-18 carbon atoms or carbons, a unsaturated alkyl group consisting of 1-18 carbon atoms carbons, aryl, arylalkyl, cycloalkyl, heteroaryl, heteroarylalkyl, heterocyclyl or, and heterocyclylalkyl;
- and
- wherein X1 is nitrogen;
- X2 is selected from NH or oxygen;
- and n is an integer between 0 and 8;
- or a pharmaceutical compositions composition thereof.
11 more elements
A composition comprising a compound of formula (1):
- wherein R1 and R2 are independently is selected from hydrogen, 2- or or 3- or 4-halo-phenyl, heteroalkyl, alkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, or and heterocyclylkalkyl;
- wherein R2 is selected from 2- or 3- or 4-halo-phenyl, heteroalkyl, alkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, and heterocyclylalkyl;
- wherein R3 is selected from alkyl, aryl, arylalkyl, cycloalkyl, heteroaryl, heteroarylalkyl, heterocyclyl, and heterocyclylalkyl, —B(R4R5), —R6—B(R4R5), R6, or —C(O)—R6, —O—R6—S(O)y—R6 (wherein y=0, 1, or 2), wherein y is 0, 1, or 2, —P(O)—(R4R5) or, and —N(R7R8);
- wherein R6 is selected from alkyl, aryl, arylalkyl, cycloalkyl, heteroaryl, heteroarylalkyl, heterocyclyl or, and heterocyclylalkyl;
- wherein R4 and R5 are independently selected from hydrogen, hydroxyl, aryloxy, or alkoxy or wherein R4 and R5 together form a cyclic ester, or an acid anhydride (either mixed or symmetrical), wherein the acid anyhydride is either mixed or symmetrical;
- wherein R7 and R8 are independently selected from hydrogen, alkyl, haloalkyl, aryl, cycloalkyl, arylalkyl, heteroalkyl, heterocyclyl or, and heterocyclylalkyl;
- R7 and R8 are both oxygen to form a nitro group;
- or R6 and R7 together with the nitrogen to which they are attached, form a heterocyclyl;
- and
- wherein X1 is nitrogen;
- X2 is —S(O)y—, wherein y= is 0, 1, or 2;
- and n is an integer between 1 and 8;
- or a pharmaceutical compositions composition thereof.
10 more elements
A composition comprising a compound of formula (1):
- wherein R1 and R2 are independently is selected from hydrogen, 2- or 3- or 4-halo-phenyl, heteroalkyl, alkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, or and heterocyclylkalkyl;
- wherein R2 is selected from 2- or 3- or 4-halo-phenyl, heteroalkyl, alkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, and heterocyclylalkyl;
- wherein R3 is selected from —B(R4R5), —R6—B(R4R5), alkyl with 2-18 carbon atoms carbons, aryl, arylalkyl, cycloalkyl, heteroaryl, heteroarylalkyl, heterocyclyl or, heterocyclylalkyl, or —C(O)—R6, —O—R6, —S(O)y—R6 (wherein y=0, 1, or 2), wherein y is 0, 1, or 2, —P(O)—(R4R5), and —N(R7R8);
- wherein R6 is selected from alkyl, aryl, arylalkyl, cycloalkyl, heteroaryl, heteroarylalkyl, heterocyclyl, and heterocyclylalkyl;
- wherein R4 and R5 are independently selected from hydrogen, hydroxyl, aryloxy, or and alkoxy, or wherein R4 and R5 together form a cyclic ester, or an acid anhydride (either mixed or symmetrical), wherein the acid anyhydride is either mixed or symmetrical;
- wherein R7 and R8 are independently selected from hydrogen, alkyl, haloalkyl, aryl, cycloalkyl, arylalkyl, heteroalkyl, heterocyclyl or heterocyclylalkyl;
- R7 and R8 are both oxygen to form a nitro group;
- or R6 and R7 and R8, together with the nitrogen to which they are attached, form a heterocyclyl;
- and
- wherein X1 is nitrogen;
- X2 is —S(O)y—, wherein y= is 0, 1, or 2;
- and n is an integer between 0 and 8;
- or a pharmaceutical compositions composition thereof.
10 more elements
A compound of formula (1):
- wherein R1 is selected from hydrogen, 2- or 3- or 4-halo-phenyl, heteroalkyl, alkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, and heterocyclylalkyl;
- wherein R2 is selected from 2- or 3- or 4-halo-phenyl, heteroalkyl, alkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, and heterocyclylalkyl;
- wherein R3 is selected from —B(R4R5), —R6—B(R4R5), alkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, R6, —O—R6, —S(O)y—R6, wherein y is 0, 1, or 2, —P(O)—(R4R5), —N(R7R8), and —C(O)—R9;
- wherein R6 is selected from alkyl, aryl, arylalkyl, cycloalkyl with 5 to 7 ring atoms, heteroaryl, heteroarylalkyl, heterocyclyl, and heterocyclylalkyl;
- wherein R4 and R5 are independently selected from hydrogen, hydroxyl, aryloxy, and alkoxy, or wherein R4 and R5 together form a cyclic ester or an acid anhydride, wherein the acid anhydride is either mixed or symmetrical;
- wherein R7 and R8 are independently selected from hydrogen, alkyl, haloalkyl, aryl, cycloalkyl, arylalkyl, heteroalkyl, heterocyclyl, and heterocyclylalkyl;
- R7 and R8 are both oxygen to form a nitro group;
- or R7 and R8 together with the nitrogen to which they are attached, form a heterocyclyl;
- wherein R9 is selected from an alkyl consisting of 1 or 3-18 carbons, a unsaturated alkyl group consisting of 1-18 carbons, aryl, arylalkyl, cycloalkyl, heteroaryl, heteroarylalkyl, heterocyclyl and heterocyclylalkyl;
- and
- wherein X1 is nitrogen;
- X2 is oxygen;
- and n is an integer between 0 and 8;
- or a pharmaceutical composition thereof.
11 more elements
A composition comprising a compound of formula (1):
- wherein R1 is selected from hydrogen, 2- or 3- or 4-halo-phenyl, heteroalkyl, alkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, and heterocyclylalkyl;
- wherein R2 is selected from 2- or 3- or 4-halo-phenyl, heteroalkyl, alkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, and heterocyclylalkyl;
- wherein R3 is selected from —B(R4R5), —R6—B(R4R5), aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, —O—R6, —S(O)y—R6, wherein y is 0, 1, or 2, —P(O)—(R4R5), —N(R7R8), and —C(O)—R9, and alkyl, wherein alkyl is unsubstituted or substituted with one or more substituents selected from hydroxy, amino, alkylamino, boronyl, nitro, and cyano;
- wherein R6 is selected from alkyl, aryl, arylalkyl, cycloalkyl with 5 to 7 ring atoms, heteroaryl, heteroarylalkyl, heterocyclyl, and heterocyclylalkyl;
- wherein R4 and R5 are independently hydrogen, hydroxyl, aryloxy, or alkoxy, or wherein R4 and R5 together form a cyclic ester, or an acid anhydride, wherein the acid anhydride is either mixed or symmetrical;
- wherein R7 and R8 are independently selected from hydrogen, alkyl, haloalkyl, aryl, cycloalkyl, arylalkyl, heteroalkyl, heterocyclyl, and heterocyclylalkyl;
- R7 and R8 are both oxygen to form a nitro group;
- or R7 and R8 together with the nitrogen to which they are attached, form a heterocyclyl;
- wherein R9 is selected from an alkyl consisting of 1 or 3-18 carbons, an unsaturated alkyl group consisting of 1-18 carbons, aryl, arylalkyl, cycloalkyl, heteroaryl, heteroarylalkyl, heterocyclyl, and heterocyclylalkyl;
- and
- wherein X1 is nitrogen;
- X2 is NH;
- and n is an integer between 0 and 8;
- or a pharmaceutical composition thereof.
11 more elements
Dependencies are inferred from the claim text.