US 2024/0199596 A1Published application

Diacylglycerol kinase modulating compounds

AssigneeGilead Sciences, Inc.

InventorsMichael Graupe, Juan A. Guerrero, Stephen D. Holmbo, Jesse M. Jacobsen, Tetsuya Kobayashi, Leena B. Patel, Heath A. Weaver, Jie Xu, Suet C. Yeung

Life of this patent

Estimating the term…

Abstract

The present disclosure provides diacylglycerol kinase modulating compounds, and pharmaceutical compositions thereof, for treating cancer, including solid tumors, and viral infections, such as HIV or hepatitis B virus infection. The compounds can be used alone or in combination with other agents.

Claims126

Dependent claims

A compound of Formula (I):

or a pharmaceutically acceptable salt thereof, wherein
R1 is hydrogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 alkoxy, halogen, C1-6 haloalkyl, C1-6 haloalkoxy, or —CN;
R2 is hydrogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C1-6 alkoxy, C2-6 alkoxyalkyl, halogen, C1-6 haloalkyl, C1-6 haloalkoxy, —CN, —NO, —NO2, —C(O)R2a, —C(O)OR2a, —OC(O)R2a, —C(O)N(R2a)(R2b), —N(R2a)C(O)R2b, —OC(O)N(R2a)(R2b), —N(R2a)C(O)OR2b, —C(—NR2a)N(R2b)(R2c), —N(R2a)(R2b), —N(R2a)N(R2b)(R2c), —N(R2a)N═C(R2b)(OR2c), —OR2a, —SR2a, —S(O)R2a, —S(O)(NR2a)(R2b), —S(NR2a)(NR2b)(R2e), —S(O)2R2a, —S(O)2N(R2a)(R2b), —N(R2a)S(O)2(R2b), —P(R2a)(R2b), —P(O)(R2a)(R2b), —P(O)(OR2a)(R2b), —P(O)(OR2a)(OR2b), C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, C6-12 aryl, C1-6 alkyl-C6-12 aryl, heterocycloalkyl, C1-6 alkyl-(heterocycloalkyl), heteroaryl, or C1-6 alkyl-(heteroaryl), wherein each alkyl, alkenyl or alkynyl is independently optionally substituted with 1 to 3 R2d groups which can be the same or different, each cycloalkyl is optionally substituted with 1 to 3 R2e groups which can be the same or different, each aryl is optionally substituted with 1 to 3 R2f groups which can be the same or different, each heterocycloalkyl is optionally substituted with 1 to 3 R2g groups which can be the same or different, and each heteroaryl is optionally substituted with 1 to 3 R2h groups which can be the same or different;
each R2a, R2b, and R2c is independently hydrogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C2-6 alkoxyalkyl, C1-6 haloalkyl, C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, C6-12 aryl, C1-6 alkyl-C6-12 aryl, heterocycloalkyl, C1-6 alkyl-(heterocycloalkyl), heteroaryl, or C1-6 alkyl-(heteroaryl), wherein the aryl or heteroaryl is optionally substituted with 1 to 3 R2j,
alternatively, R2a, R2b, and R2c when attached to the same atom can be combined with the atom to which they are attached to form a heterocycloalkyl;
each R2d is independently —CN, —C(O)R2d1, —C(O)OR2d1, —OC(O)R2d1, —C(O)N(R2d1)(R2d2), —N(R2d1)C(O)R2d2, —OC(O)N(R2d1)(R2d2), —N(R2d1)C(O)OR2d2, —N(R2d1)(R2d2), ═O, —OR2d1, —SR2d1, —S(O)R2d1, —S(O)(NR2d1)(R2d2), —S(O)2R2d1, —S(O)N(R2d1)(R2d2), —N(R2d1)S(O)2R2d2, C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, C6-12 aryl, C1-6 alkyl-C6-12 aryl, heterocycloalkyl, C1-6 alkyl-(heterocycloalkyl), heteroaryl, or C1-6 alkyl-(heteroaryl);
each R2d1 and R2d2 is independently hydrogen, C1-6 alkyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C2-6 alkoxyalkyl, or C1-6 haloalkyl;
each R2e, R2f, R2g, and R2h is independently hydrogen, C1-6 alkyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C1-6 alkoxy, C2-6 alkoxyalkyl, halogen, C1-6 haloalkyl, C1-6 haloalkoxy, —CN, or —OH;
each R2j is independently C1-6 alkyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C1-6 alkoxy, C2-6 alkoxyalkyl, halogen, C1-6 haloalkyl, or C1-6 haloalkoxy;
R3 is hydrogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C1-6 alkoxy, C2-6 alkoxyalkyl, halogen, C1-6 haloalkyl, C1-6 haloalkoxy, —CN, —NO, —NO2, —C(O)R3a, —C(O)OR3a, —OC(O)R3a, —C(O)N(R3a)(R3b), —N(R3a)C(O)R3b, —OC(O)N(R3a)(R3b), —N(R3a)C(O)OR3b, —C(═NR3a)N(R3b)(R3c), —N(R3a)(R3b), —N(R3a)N(R3b)(R3c), —N(R3a)N═C(R3b)(OR3c), —OR3a, —SR3a, —S(O)R3a, —S(O)(NR3a)(R3b), —S(NR3a)(NR3b)(R3c), —S(O)2R3a, —S(O)2N(R3a)(R3b), —N(R3a)S(O)2(R3b), —P(R3a)(R3b), —P(O)(R3a)(R3b), —P(O)(OR3a)(R3b), —P(O)(OR3a)(OR3b), C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, C6-12 aryl, C1-6 alkyl-C6-12 aryl, heterocycloalkyl, C1-6 alkyl-(heterocycloalkyl), heteroaryl, or C1-6 alkyl-(heteroaryl), wherein each alkenyl or alkynyl is independently optionally substituted with 1 to 3 R3d groups, each cycloalkyl is optionally substituted with 1 to 3 R3e groups, each aryl is optionally substituted with 1 to 3 R3f groups which can be the same or different, each heterocycloalkyl is optionally substituted with 1 to 3 R3g groups which can be the same or different, and each heteroaryl is optionally substituted with 1 to 3 R3h groups which can be the same or different;
each R3a, R3b, and R3c is independently hydrogen, C1-6 alkyl, C1-6 hydroxyalkyl, C2-6 alkoxyalkyl, C1-6 haloalkyl, C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, C6-12 aryl, C1-6 alkyl-C6-12 aryl, heterocycloalkyl, or heteroaryl;
alternatively, R3a, R3b, and R3c when attached to the same atom can be combined with the atom to which they are attached to form a heterocycloalkyl;
each R3d is independently —N(R3d1)(R3d2), —OR3d1, C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, C6-12 aryl, C1-6 alkyl-C6-12 aryl, heterocycloalkyl, or heteroaryl;
each R3d1 and R3d2 is independently hydrogen, C1-6 alkyl, or —C(O)O—(C1-6 alkyl);
each R3e, R3f, R3g, and R3h is independently hydrogen, C1-6 alkyl, C1-6 alkoxy, halogen, C1-6 haloalkyl or C1-6 haloalkoxy;
R4 is hydrogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 alkoxy, halogen, C1-6 haloalkyl, C1-6 haloalkoxy, or —CN;
R5 is C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 hydroxyalkyl, C2-6 alkoxyalkyl, C1-6 haloalkyl, C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, C6-12 aryl, C1-6 alkyl-C6-12 aryl, heterocycloalkyl, C1-6 alkyl-(heterocycloalkyl), heteroaryl, or C1-6 alkyl-(heteroaryl), wherein the alkyl is optionally substituted with R5a,
R5a is —OSi(R5a1)(R5a2)(R5a3);
R5a1, R5a2, and R5a3 are each independently C1-6 alkyl;
and
R6 is C2-6 alkenyl, C2-6 alkynyl, C1-6 haloalkyl, C6-12 aryl substituted with 1 to 3 R6a which can be the same or different, or heteroaryl optionally substituted with 1 to 3 R6a which can be the same or different;
each R6a is independently C1-6 alkyl, C2-6 alkenyl, C2-8 alkynyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C1-6 alkoxy, C2-6 alkoxyalkyl, halogen, C1-6 haloalkyl, C1-6 haloalkoxy, —CN, —NO2, —C(O)R6b, —OC(O)R6b, —C(O)N(R6b)(R6c), —N(R6b)C(O)R6, —C(═NR6b)N(R6c)(R6d), —N(R6b)(R6c), —OR6b, —SR6b, —S(O)R6b, —S(O)2R6b, —S(NR6b)(NR6c)R6d, —S(O)(NR6b)(R6c), —S(O)2N(R6b)(R6c), —N(R6b)S(O)2(R6c), —P(R6b)(R6c), —P(O)(R6b)(R6c), —P(O)(OR6b)(R6c), —P(O)(OR6b)(OR6c), C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, C6-12 aryl, C1-6 alkyl-C6-12 aryl, heterocycloalkyl, C1-6 alkyl-(heterocycloalkyl), heteroaryl, or C1-6 alkyl-(heteroaryl), wherein the cycloalkyl, aryl, heterocycloalkyl, or heteroaryl is each optionally substituted with 1 to 3 R6e which can be the same or different, the alkyl is optionally substituted with R6f, and the alkynyl is optionally substituted with 1 to 4 R6j which can be the same or different;
each R6b, R6c and R6d is independently hydrogen, C1-6 alkyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C2-6 alkoxyalkyl, C1-6 haloalkyl, C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, C6-12 aryl, C1-6 alkyl-C6-12 aryl, heterocycloalkyl, C1-6 alkyl-(heterocycloalkyl), heteroaryl, or C1-6 alkyl-(heteroaryl), wherein the cycloalkyl, aryl, heterocycloalkyl, or heteroaryl is optionally substituted by 1 to 3 R6k which can be the same or different;
each R6k is independently C1-6 alkyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C1-6 alkoxy, C2-6 alkoxyalkyl, C1-6 haloalkyl, C1-6 haloalkoxy, C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, heterocycloalkyl, or C1-6 alkyl-(heterocycloalkyl);
each R6e is independently C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C1-6 alkoxy, C2-6 alkoxyalkyl, halogen, C1-6 haloalkyl, C1-6 haloalkoxy, —CN, —NO2, —C(O)R6e1, —C(O)OR6e1, —OC(O)R6e1, —C(O)N(R6e1)(R6e2), —N(R6e1)C(O)R6e2, —OC(O)N(R6e1)(R6g2), —N(R6e1)C(O)OR6e2, —C(═NR6e1)N(R6e2)(R6e3), —N(R6e1)(R6e2), ═O, —OR6e1, —SR6e1, —S(O)R6e1, —S(NR6e1)(NR6e2), —S(O)(NR6e1)(R6e2), —S(O)2R6e1, —S(O)2N(R6e1)(R6e2), —SF5, —N(R6e1)S(O)2(R6e2), —P(R6e1)(R6e2), —P(O)(R6e1)(R6e2), —P(O)(OR6e1)(R6e2), —P(O)(OR6e1)(OR6e2), —Si(R6e1)(R6e2)(R6e3), C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, C6-12 aryl, C1-6 alkyl-C6-12 aryl, heterocycloalkyl, C1-6 alkyl-heterocycloalkyl, heteroaryl, or C1-6 alkyl-heteroaryl, wherein the cycloalkyl, aryl, heterocycloalkyl, or heteroaryl is each optionally substituted with 1 to 3 R6h which can be the same or different, and the alkyl is optionally substituted with 1 to 3 R6m which can be the same or different;
each R6e1, R6e2, and R6e3 is independently hydrogen, C1-6 alkyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C1-6 alkoxyalkyl, C1-6 haloalkyl, C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, C6-10 aryl, C1-6 alkyl-C6-10 aryl, heterocycloalkyl, C1-6 alkyl-(heterocycloalkyl), heteroaryl, or C1-6 alkyl-(heteroaryl), wherein the cycloalkyl, aryl, heterocycloalkyl, or heteroaryl is optionally substituted with 1 to 3 R6n which can be the same or different;
each R6n is C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C1-6 alkoxy, C2-6 alkoxyalkyl, halogen, C1-6 haloalkyl, C1-6 haloalkoxy, —CN, —C(O)R6n1, —C(O)OR6n1, —OC(O)R6n1, —C(O)N(R6n1)(R6n2), —N(R6n1)C(O)R6n2, —OC(O)N(R6n1)(R6n2), —N(R6n1)C(O)OR6n2, —C(═NR6n1)N(R6n2)(R6n3), —N(R6n1)(R6n2), ═O, —OH, —SR6n1, —S(O)R6n1, —S(NR6n1)(NR6n2) R6n3, —S(O)(NR6n1)(R6n2), —S(O)2R6n1, —S(O)2N(R6n1)(R6n2), or —N(R6n1)S(O)2(R6n2);
each R6n1, R6n2 and R6n3 is independently hydrogen, C1-6 alkyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C2-6 alkoxyalkyl, C1-6 haloalkyl, C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, C6-10 aryl, C1-6 alkyl-C6-10 aryl, heterocycloalkyl, C1-6 alkyl-(heterocycloalkyl), heteroaryl, or C1-6 alkyl-(heteroaryl);
each R6h is independently C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C1-6 alkoxy, C2-6 alkoxyalkyl, halogen, C1-6 haloalkyl, C1-6 haloalkoxy, —CN, —C(O)R6h1, —C(O)OR6h1, —OC(O)R6h1, —C(O)N(R6h1)(R6h2), —N(R6h1)C(O)R6h2, —OC(O)N(R6h1)(R6h2), —N(R6h1)C(O)OR6h2, —C(═NR6h1)N(R6h2)(R6h3), —N(R6h1)(R6h2), ═O, —OH, —SR6h1, —S(O)R6h1, —S(NR6h1)(NR6h2)R6h3, —S(O)(NR6h1)(R6h2), —S(O)2R6h1, —S(O)2N(R6h1)(R6h2), —N(R6h1)S(O)2(R6h2), C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, heterocycloalkyl, or C1-6 alkyl-(heterocycloalkyl);
each R6h1, R6h2, and R6h3 is independently hydrogen, C1-6 alkyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C2-6 alkoxyalkyl, C1-6 haloalkyl, C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, C6-10 aryl, C1-6 alkyl-C6-10 aryl, heterocycloalkyl, C1-6 alkyl-(heterocycloalkyl), heteroaryl, or C1-6 alkyl-(heteroaryl);
each R6m is independently halogen, C1-6 haloalkyl, C1-6 haloalkoxy, —CN, —C(O)R6m1, —C(O)OR6m1, —OC(O)R6m1, —C(O)N(R6m1)(R6m2), —N(R6m3)C(O)R6m2, —OC(O)N(R6m1)(R6m2), —N(R6m1)C(O)OR6m2, —C(═NR6m3)N(R6m1)(R6m2), —N(R6m1)(R6m2), ═O, —OH, —SR6m1, —S(O)R6m1, —S(NR6m1)(NR6m2) R6m3, —S(O)(NR6m1)(R6m2), —S(O)2R6m1, —S(O)2N(R6m1)(R6m2), or —N(R6m3)S(O)2(R6m2);
each R6m1, R6m2, and R6m3 is independently hydrogen, C1-6 alkyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C2-6 alkoxyalkyl, C1-6 haloalkyl, C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, C6-10 aryl, C1-6 alkyl-C6-10 aryl, heterocycloalkyl, C1-6 alkyl-(heterocycloalkyl), heteroaryl, or C1-6 alkyl-(heteroaryl);
R6f is —OSi(R6f1)(R6f2)(R6f3);
R6f1, R6f2, and R6f3 are each independently C1-6 alkyl;
each R6j is independently C2-6 alkoxyalkyl, halogen, C1-6 haloalkyl, C1-6 haloalkoxy, —CN, —C(O)R6j1, —C(O)OR6j1, —OC(O)R6j1, —C(O)N(R6j1)(R6j2), —N(R6j1)C(O)R6j2, —OC(O)N(R6j1)(R6j2), —N(R6j1)C(O)OR6j2, —C(═NR6j3)N(R6j1)(R6j2), —N(R6j1)(R6j2), ═O, —OR6j1, —SR6j1, —S(O)R6j1, —S(NR6j1)(NR6j2), —S(NR6j1)(NR6j2)R6j3, —S(O)(NR6j1)(R6j2), —S(O)2R6j1, —S(O)2N(R6j1)(R6j2), —N(R6j1)S(O)2(R6j2), —Si(R6j1)(R6j2)(R6j3), C3-10 cycloalkyl, C6-12 aryl, heterocycloalkyl, or heteroaryl, wherein the cycloalkyl, aryl, heterocycloalkyl, or heteroaryl is optionally substituted with 1 to 3 R6p which can be the same or different;
each R6j1, R6j2, and R6j3 is independently hydrogen, C1-6 alkyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C2-6 alkoxyalkyl, C1-6 haloalkyl, C3-10 cycloalkyl optionally substituted with C1-6 haloalkyl, C1-6 alkyl-C3-10 cycloalkyl, C6-10 aryl, C1-6 alkyl-C6-10 aryl, heterocycloalkyl, C1-6 alkyl-(heterocycloalkyl), heteroaryl, or C1-6 alkyl-(heteroaryl);
each R6p is independently C1-6 alkyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C1-6 alkoxy, C2-6 alkoxyalkyl, halogen, C1-6 haloalkyl, C1-6 haloalkoxy, —CN, —C(O)R6p1, —C(O)OR6p1, —OC(O)R6p1, —C(O)N(R6p1)(R6p2), —N(R6p1)C(O)R6p2, —OC(O)N(R6p1)(R6p2), —N(R6p1)C(O)OR6p2, —C(═NR6p3)N(R6p1)(R6p2), —N(R6p1)(R6p2), ═O, —OH, —SR6p1, —S(O)R6p1, —S(NR6p1)(NR6p2)R6p3, S(O)(NR6p1)(R6p2), —S(O)2R6p1, —S(O)2N(R6p1)(R6p2), or —N(R6p1)S(O)2(R6p2);
each R6p1, R6p2, and R6p3 is independently hydrogen, C1-6 alkyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C2-6 alkoxyalkyl, C1-6 haloalkyl, C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, C6-10 aryl, C1-6 alkyl-C6-10 aryl, heterocycloalkyl, C1-6 alkyl-(heterocycloalkyl), heteroaryl, or C1-6 alkyl-(heteroaryl);
or R5 and one R6a together with the atoms to which they are attached form a heterocycloalkyl, optionally substituted with 1 to 3 R6g which can be the same or different;
each R6g is independently C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C2-6 alkoxyalkyl, halogen, C1-6 haloalkyl, C1-6 haloalkoxy, or —CN;
R7 is hydrogen, C1-6 alkyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C2-6 alkoxyalkyl, C1-6 haloalkyl, C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, heterocycloalkyl, or C1-6 alkyl-(heterocycloalkyl);
each heterocycloalkyl is a 3 to 20 membered ring having 1 to 4 heteroatoms each independently N, O or S;
and
each heteroaryl is a 5 to 18 membered ring having 1 to 4 heteroatoms each independently N, O or S.

41 more elements

A compound of Formula (I):

or a pharmaceutically acceptable salt thereof, wherein
R1 is hydrogen, C1-6 alkyl, or halogen;
R2 is hydrogen, C1-6 alkyl, or halogen;
R3 is hydrogen, C1-6 alkyl, or halogen;
R4 is hydrogen, C1-6 alkyl, or halogen;
R7 is hydrogen or C1-6 alkyl optionally substituted with —OH;
R5 is C1-6 alkyl or C1-6 haloalkyl;
R6 is phenyl substituted with 1 to 3 R6a which can be the same or different, or heteroaryl optionally substituted with 1 to 3 R6a which can be the same or different, wherein the heteroaryl is a 5 or 6 membered ring having 1 to 3 heteroatoms each independently N, O or S;
or
X3, X4, X3, and X6 are each independently CH, N, or C—R6a, provided that not more than two of X3, X4, X5, and X6 are N, and not more than two of X3, X4, X5, and X6 are C—R6a, and
Ring A is a 5 to 8 membered heterocycloalkyl optionally having 1 to 2 additional heteroatoms each independently N, O, or S, and optionally Ring A is substituted with 1 or 2 R6g which can be the same or different;
each R6a is independently halogen, C2-8 alkynyl, phenyl, heterocycloalkyl, or heteroaryl, wherein the phenyl, heterocycloalkyl, or heteroaryl is each optionally substituted with 1 to 3 R6e, and the alkynyl is optionally substituted with 1 to 4 R6j which can be the same or different, wherein the heterocycloalkyl is a 3 to 10 membered ring having 1 to 3 heteroatoms each independently N, O or S, the heteroaryl is a 5 or 6 membered ring having 1 to 3 heteroatoms each independently N, O or S;
each R6j is independently halogen, C1-6 haloalkyl, —OR6j1, —CN, —N(R6j1)(R6j2), —N(R6j1)C(O)R6j2, C3-10 cycloalkyl, heteroaryl, or heterocycloalkyl, wherein the cycloalkyl, heteroaryl, or heterocycloalkyl is optionally substituted with 1 to 3 R6p which can be the same or different, the heterocycloalkyl is a 3 to 10 membered ring having 1 to 3 heteroatoms each independently N, O or S;
the heteroaryl is a 5 or 6 membered ring having 1 to 3 heteroatoms each independently N, O or S;
each R6j1 and R6j2 is independently hydrogen, C1-6 alkyl, C1-6 haloalkyl, or C3-10 cycloalkyl optionally substituted with C1-6 haloalkyl;
each R6p is independently halogen, C1-6 alkyl, C1-6 haloalkyl, —C(O)R6p1, or heterocycloalkyl, the heterocycloalky is a 3 to 10 membered ring having 1 to 3 heteroatoms each independently N, O or S;
R6p1 is C1-6 alkyl, or C3-10 cycloalkyl;
each R6e is independently C1-6 alkyl, C3-6 cycloalkyl, heterocycloalkyl, halogen, C1-6 haloalkyl, or —CN, wherein the cycloalkyl and heterocycloalkyl are optionally substituted with 1 to 3 R6h which can be the same or different, the heterocycloalkyl is a 3 to 10 membered ring having 1 to 3 heteroatoms each independently N, O or S;
each R6h is independently C1-6 alkyl, C1-6 haloalkyl, ═O, or —OH;
and
each R6g is independently C1-6 alkyl, halogen, or C1-6 haloalkyl.

18 more elements

The compound of any one of the preceding claims, or a pharmaceutically acceptable salt thereof, wherein

R6 is phenyl substituted with C2-8 alkynyl, the alkynyl is substituted with 1 or 2 R6j which can be the same or different;
and
the phenyl is optionally substituted with one additional R6a.

Dependencies are inferred from the claim text.

Facts

Application: 18/413,767Filed 16 Jan 2024
Priority: 23 Jun 2021
Published: 20 Jun 2024
Term ends: Not estimatedThe source records don’t support an estimate.

Classification25 codes

C07D 413/14
Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms:…
A61K 31/517
Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim: ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
A61K 31/55
Having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins: having seven-membered rings, e.g. azelastine, pentylenetetrazole
A61K 31/553
Having seven-membered rings, e.g. azelastine, pentylenetetrazole: having at least one nitrogen and one oxygen as ring hetero atoms, e.g. loxapine,…

Family

Application63/213,893Us provisional application · filed 23 Jun 2021
Application17/845,469Continuation · filed 21 Jun 2022
Application18/413,767Continuation
US 11,932,634 B2Related patent
US 2023/0060004 A1Published application
US 2024/0199596 A1This patent

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

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Abstract

A compound of Formula (I):

or a pharmaceutically acceptable salt thereof, wherein
R1 is hydrogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 alkoxy, halogen, C1-6 haloalkyl, C1-6 haloalkoxy, or —CN;
R2 is hydrogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C1-6 alkoxy, C2-6 alkoxyalkyl, halogen, C1-6 haloalkyl, C1-6 haloalkoxy, —CN, —NO, —NO2, —C(O)R2a, —C(O)OR2a, —OC(O)R2a, —C(O)N(R2a)(R2b), —N(R2a)C(O)R2b, —OC(O)N(R2a)(R2b), —N(R2a)C(O)OR2b, —C(—NR2a)N(R2b)(R2c), —N(R2a)(R2b), —N(R2a)N(R2b)(R2c), —N(R2a)N═C(R2b)(OR2c), —OR2a, —SR2a, —S(O)R2a, —S(O)(NR2a)(R2b), —S(NR2a)(NR2b)(R2e), —S(O)2R2a, —S(O)2N(R2a)(R2b), —N(R2a)S(O)2(R2b), —P(R2a)(R2b), —P(O)(R2a)(R2b), —P(O)(OR2a)(R2b), —P(O)(OR2a)(OR2b), C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, C6-12 aryl, C1-6 alkyl-C6-12 aryl, heterocycloalkyl, C1-6 alkyl-(heterocycloalkyl), heteroaryl, or C1-6 alkyl-(heteroaryl), wherein each alkyl, alkenyl or alkynyl is independently optionally substituted with 1 to 3 R2d groups which can be the same or different, each cycloalkyl is optionally substituted with 1 to 3 R2e groups which can be the same or different, each aryl is optionally substituted with 1 to 3 R2f groups which can be the same or different, each heterocycloalkyl is optionally substituted with 1 to 3 R2g groups which can be the same or different, and each heteroaryl is optionally substituted with 1 to 3 R2h groups which can be the same or different;
each R2a, R2b, and R2c is independently hydrogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C2-6 alkoxyalkyl, C1-6 haloalkyl, C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, C6-12 aryl, C1-6 alkyl-C6-12 aryl, heterocycloalkyl, C1-6 alkyl-(heterocycloalkyl), heteroaryl, or C1-6 alkyl-(heteroaryl), wherein the aryl or heteroaryl is optionally substituted with 1 to 3 R2j,
alternatively, R2a, R2b, and R2c when attached to the same atom can be combined with the atom to which they are attached to form a heterocycloalkyl;
each R2d is independently —CN, —C(O)R2d1, —C(O)OR2d1, —OC(O)R2d1, —C(O)N(R2d1)(R2d2), —N(R2d1)C(O)R2d2, —OC(O)N(R2d1)(R2d2), —N(R2d1)C(O)OR2d2, —N(R2d1)(R2d2), ═O, —OR2d1, —SR2d1, —S(O)R2d1, —S(O)(NR2d1)(R2d2), —S(O)2R2d1, —S(O)N(R2d1)(R2d2), —N(R2d1)S(O)2R2d2, C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, C6-12 aryl, C1-6 alkyl-C6-12 aryl, heterocycloalkyl, C1-6 alkyl-(heterocycloalkyl), heteroaryl, or C1-6 alkyl-(heteroaryl);
each R2d1 and R2d2 is independently hydrogen, C1-6 alkyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C2-6 alkoxyalkyl, or C1-6 haloalkyl;
each R2e, R2f, R2g, and R2h is independently hydrogen, C1-6 alkyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C1-6 alkoxy, C2-6 alkoxyalkyl, halogen, C1-6 haloalkyl, C1-6 haloalkoxy, —CN, or —OH;
each R2j is independently C1-6 alkyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C1-6 alkoxy, C2-6 alkoxyalkyl, halogen, C1-6 haloalkyl, or C1-6 haloalkoxy;
R3 is hydrogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C1-6 alkoxy, C2-6 alkoxyalkyl, halogen, C1-6 haloalkyl, C1-6 haloalkoxy, —CN, —NO, —NO2, —C(O)R3a, —C(O)OR3a, —OC(O)R3a, —C(O)N(R3a)(R3b), —N(R3a)C(O)R3b, —OC(O)N(R3a)(R3b), —N(R3a)C(O)OR3b, —C(═NR3a)N(R3b)(R3c), —N(R3a)(R3b), —N(R3a)N(R3b)(R3c), —N(R3a)N═C(R3b)(OR3c), —OR3a, —SR3a, —S(O)R3a, —S(O)(NR3a)(R3b), —S(NR3a)(NR3b)(R3c), —S(O)2R3a, —S(O)2N(R3a)(R3b), —N(R3a)S(O)2(R3b), —P(R3a)(R3b), —P(O)(R3a)(R3b), —P(O)(OR3a)(R3b), —P(O)(OR3a)(OR3b), C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, C6-12 aryl, C1-6 alkyl-C6-12 aryl, heterocycloalkyl, C1-6 alkyl-(heterocycloalkyl), heteroaryl, or C1-6 alkyl-(heteroaryl), wherein each alkenyl or alkynyl is independently optionally substituted with 1 to 3 R3d groups, each cycloalkyl is optionally substituted with 1 to 3 R3e groups, each aryl is optionally substituted with 1 to 3 R3f groups which can be the same or different, each heterocycloalkyl is optionally substituted with 1 to 3 R3g groups which can be the same or different, and each heteroaryl is optionally substituted with 1 to 3 R3h groups which can be the same or different;
each R3a, R3b, and R3c is independently hydrogen, C1-6 alkyl, C1-6 hydroxyalkyl, C2-6 alkoxyalkyl, C1-6 haloalkyl, C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, C6-12 aryl, C1-6 alkyl-C6-12 aryl, heterocycloalkyl, or heteroaryl;
alternatively, R3a, R3b, and R3c when attached to the same atom can be combined with the atom to which they are attached to form a heterocycloalkyl;
each R3d is independently —N(R3d1)(R3d2), —OR3d1, C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, C6-12 aryl, C1-6 alkyl-C6-12 aryl, heterocycloalkyl, or heteroaryl;
each R3d1 and R3d2 is independently hydrogen, C1-6 alkyl, or —C(O)O—(C1-6 alkyl);
each R3e, R3f, R3g, and R3h is independently hydrogen, C1-6 alkyl, C1-6 alkoxy, halogen, C1-6 haloalkyl or C1-6 haloalkoxy;
R4 is hydrogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 alkoxy, halogen, C1-6 haloalkyl, C1-6 haloalkoxy, or —CN;
R5 is C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 hydroxyalkyl, C2-6 alkoxyalkyl, C1-6 haloalkyl, C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, C6-12 aryl, C1-6 alkyl-C6-12 aryl, heterocycloalkyl, C1-6 alkyl-(heterocycloalkyl), heteroaryl, or C1-6 alkyl-(heteroaryl), wherein the alkyl is optionally substituted with R5a,
R5a is —OSi(R5a1)(R5a2)(R5a3);
R5a1, R5a2, and R5a3 are each independently C1-6 alkyl;
and
R6 is C2-6 alkenyl, C2-6 alkynyl, C1-6 haloalkyl, C6-12 aryl substituted with 1 to 3 R6a which can be the same or different, or heteroaryl optionally substituted with 1 to 3 R6a which can be the same or different;
each R6a is independently C1-6 alkyl, C2-6 alkenyl, C2-8 alkynyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C1-6 alkoxy, C2-6 alkoxyalkyl, halogen, C1-6 haloalkyl, C1-6 haloalkoxy, —CN, —NO2, —C(O)R6b, —OC(O)R6b, —C(O)N(R6b)(R6c), —N(R6b)C(O)R6, —C(═NR6b)N(R6c)(R6d), —N(R6b)(R6c), —OR6b, —SR6b, —S(O)R6b, —S(O)2R6b, —S(NR6b)(NR6c)R6d, —S(O)(NR6b)(R6c), —S(O)2N(R6b)(R6c), —N(R6b)S(O)2(R6c), —P(R6b)(R6c), —P(O)(R6b)(R6c), —P(O)(OR6b)(R6c), —P(O)(OR6b)(OR6c), C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, C6-12 aryl, C1-6 alkyl-C6-12 aryl, heterocycloalkyl, C1-6 alkyl-(heterocycloalkyl), heteroaryl, or C1-6 alkyl-(heteroaryl), wherein the cycloalkyl, aryl, heterocycloalkyl, or heteroaryl is each optionally substituted with 1 to 3 R6e which can be the same or different, the alkyl is optionally substituted with R6f, and the alkynyl is optionally substituted with 1 to 4 R6j which can be the same or different;
each R6b, R6c and R6d is independently hydrogen, C1-6 alkyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C2-6 alkoxyalkyl, C1-6 haloalkyl, C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, C6-12 aryl, C1-6 alkyl-C6-12 aryl, heterocycloalkyl, C1-6 alkyl-(heterocycloalkyl), heteroaryl, or C1-6 alkyl-(heteroaryl), wherein the cycloalkyl, aryl, heterocycloalkyl, or heteroaryl is optionally substituted by 1 to 3 R6k which can be the same or different;
each R6k is independently C1-6 alkyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C1-6 alkoxy, C2-6 alkoxyalkyl, C1-6 haloalkyl, C1-6 haloalkoxy, C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, heterocycloalkyl, or C1-6 alkyl-(heterocycloalkyl);
each R6e is independently C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C1-6 alkoxy, C2-6 alkoxyalkyl, halogen, C1-6 haloalkyl, C1-6 haloalkoxy, —CN, —NO2, —C(O)R6e1, —C(O)OR6e1, —OC(O)R6e1, —C(O)N(R6e1)(R6e2), —N(R6e1)C(O)R6e2, —OC(O)N(R6e1)(R6g2), —N(R6e1)C(O)OR6e2, —C(═NR6e1)N(R6e2)(R6e3), —N(R6e1)(R6e2), ═O, —OR6e1, —SR6e1, —S(O)R6e1, —S(NR6e1)(NR6e2), —S(O)(NR6e1)(R6e2), —S(O)2R6e1, —S(O)2N(R6e1)(R6e2), —SF5, —N(R6e1)S(O)2(R6e2), —P(R6e1)(R6e2), —P(O)(R6e1)(R6e2), —P(O)(OR6e1)(R6e2), —P(O)(OR6e1)(OR6e2), —Si(R6e1)(R6e2)(R6e3), C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, C6-12 aryl, C1-6 alkyl-C6-12 aryl, heterocycloalkyl, C1-6 alkyl-heterocycloalkyl, heteroaryl, or C1-6 alkyl-heteroaryl, wherein the cycloalkyl, aryl, heterocycloalkyl, or heteroaryl is each optionally substituted with 1 to 3 R6h which can be the same or different, and the alkyl is optionally substituted with 1 to 3 R6m which can be the same or different;
each R6e1, R6e2, and R6e3 is independently hydrogen, C1-6 alkyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C1-6 alkoxyalkyl, C1-6 haloalkyl, C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, C6-10 aryl, C1-6 alkyl-C6-10 aryl, heterocycloalkyl, C1-6 alkyl-(heterocycloalkyl), heteroaryl, or C1-6 alkyl-(heteroaryl), wherein the cycloalkyl, aryl, heterocycloalkyl, or heteroaryl is optionally substituted with 1 to 3 R6n which can be the same or different;
each R6n is C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C1-6 alkoxy, C2-6 alkoxyalkyl, halogen, C1-6 haloalkyl, C1-6 haloalkoxy, —CN, —C(O)R6n1, —C(O)OR6n1, —OC(O)R6n1, —C(O)N(R6n1)(R6n2), —N(R6n1)C(O)R6n2, —OC(O)N(R6n1)(R6n2), —N(R6n1)C(O)OR6n2, —C(═NR6n1)N(R6n2)(R6n3), —N(R6n1)(R6n2), ═O, —OH, —SR6n1, —S(O)R6n1, —S(NR6n1)(NR6n2) R6n3, —S(O)(NR6n1)(R6n2), —S(O)2R6n1, —S(O)2N(R6n1)(R6n2), or —N(R6n1)S(O)2(R6n2);
each R6n1, R6n2 and R6n3 is independently hydrogen, C1-6 alkyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C2-6 alkoxyalkyl, C1-6 haloalkyl, C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, C6-10 aryl, C1-6 alkyl-C6-10 aryl, heterocycloalkyl, C1-6 alkyl-(heterocycloalkyl), heteroaryl, or C1-6 alkyl-(heteroaryl);
each R6h is independently C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C1-6 alkoxy, C2-6 alkoxyalkyl, halogen, C1-6 haloalkyl, C1-6 haloalkoxy, —CN, —C(O)R6h1, —C(O)OR6h1, —OC(O)R6h1, —C(O)N(R6h1)(R6h2), —N(R6h1)C(O)R6h2, —OC(O)N(R6h1)(R6h2), —N(R6h1)C(O)OR6h2, —C(═NR6h1)N(R6h2)(R6h3), —N(R6h1)(R6h2), ═O, —OH, —SR6h1, —S(O)R6h1, —S(NR6h1)(NR6h2)R6h3, —S(O)(NR6h1)(R6h2), —S(O)2R6h1, —S(O)2N(R6h1)(R6h2), —N(R6h1)S(O)2(R6h2), C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, heterocycloalkyl, or C1-6 alkyl-(heterocycloalkyl);
each R6h1, R6h2, and R6h3 is independently hydrogen, C1-6 alkyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C2-6 alkoxyalkyl, C1-6 haloalkyl, C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, C6-10 aryl, C1-6 alkyl-C6-10 aryl, heterocycloalkyl, C1-6 alkyl-(heterocycloalkyl), heteroaryl, or C1-6 alkyl-(heteroaryl);
each R6m is independently halogen, C1-6 haloalkyl, C1-6 haloalkoxy, —CN, —C(O)R6m1, —C(O)OR6m1, —OC(O)R6m1, —C(O)N(R6m1)(R6m2), —N(R6m3)C(O)R6m2, —OC(O)N(R6m1)(R6m2), —N(R6m1)C(O)OR6m2, —C(═NR6m3)N(R6m1)(R6m2), —N(R6m1)(R6m2), ═O, —OH, —SR6m1, —S(O)R6m1, —S(NR6m1)(NR6m2) R6m3, —S(O)(NR6m1)(R6m2), —S(O)2R6m1, —S(O)2N(R6m1)(R6m2), or —N(R6m3)S(O)2(R6m2);
each R6m1, R6m2, and R6m3 is independently hydrogen, C1-6 alkyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C2-6 alkoxyalkyl, C1-6 haloalkyl, C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, C6-10 aryl, C1-6 alkyl-C6-10 aryl, heterocycloalkyl, C1-6 alkyl-(heterocycloalkyl), heteroaryl, or C1-6 alkyl-(heteroaryl);
R6f is —OSi(R6f1)(R6f2)(R6f3);
R6f1, R6f2, and R6f3 are each independently C1-6 alkyl;
each R6j is independently C2-6 alkoxyalkyl, halogen, C1-6 haloalkyl, C1-6 haloalkoxy, —CN, —C(O)R6j1, —C(O)OR6j1, —OC(O)R6j1, —C(O)N(R6j1)(R6j2), —N(R6j1)C(O)R6j2, —OC(O)N(R6j1)(R6j2), —N(R6j1)C(O)OR6j2, —C(═NR6j3)N(R6j1)(R6j2), —N(R6j1)(R6j2), ═O, —OR6j1, —SR6j1, —S(O)R6j1, —S(NR6j1)(NR6j2), —S(NR6j1)(NR6j2)R6j3, —S(O)(NR6j1)(R6j2), —S(O)2R6j1, —S(O)2N(R6j1)(R6j2), —N(R6j1)S(O)2(R6j2), —Si(R6j1)(R6j2)(R6j3), C3-10 cycloalkyl, C6-12 aryl, heterocycloalkyl, or heteroaryl, wherein the cycloalkyl, aryl, heterocycloalkyl, or heteroaryl is optionally substituted with 1 to 3 R6p which can be the same or different;
each R6j1, R6j2, and R6j3 is independently hydrogen, C1-6 alkyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C2-6 alkoxyalkyl, C1-6 haloalkyl, C3-10 cycloalkyl optionally substituted with C1-6 haloalkyl, C1-6 alkyl-C3-10 cycloalkyl, C6-10 aryl, C1-6 alkyl-C6-10 aryl, heterocycloalkyl, C1-6 alkyl-(heterocycloalkyl), heteroaryl, or C1-6 alkyl-(heteroaryl);
each R6p is independently C1-6 alkyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C1-6 alkoxy, C2-6 alkoxyalkyl, halogen, C1-6 haloalkyl, C1-6 haloalkoxy, —CN, —C(O)R6p1, —C(O)OR6p1, —OC(O)R6p1, —C(O)N(R6p1)(R6p2), —N(R6p1)C(O)R6p2, —OC(O)N(R6p1)(R6p2), —N(R6p1)C(O)OR6p2, —C(═NR6p3)N(R6p1)(R6p2), —N(R6p1)(R6p2), ═O, —OH, —SR6p1, —S(O)R6p1, —S(NR6p1)(NR6p2)R6p3, S(O)(NR6p1)(R6p2), —S(O)2R6p1, —S(O)2N(R6p1)(R6p2), or —N(R6p1)S(O)2(R6p2);
each R6p1, R6p2, and R6p3 is independently hydrogen, C1-6 alkyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C2-6 alkoxyalkyl, C1-6 haloalkyl, C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, C6-10 aryl, C1-6 alkyl-C6-10 aryl, heterocycloalkyl, C1-6 alkyl-(heterocycloalkyl), heteroaryl, or C1-6 alkyl-(heteroaryl);
or R5 and one R6a together with the atoms to which they are attached form a heterocycloalkyl, optionally substituted with 1 to 3 R6g which can be the same or different;
each R6g is independently C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C2-6 alkoxyalkyl, halogen, C1-6 haloalkyl, C1-6 haloalkoxy, or —CN;
R7 is hydrogen, C1-6 alkyl, C1-6 hydroxyalkyl, C1-6 aminoalkyl, C2-6 alkoxyalkyl, C1-6 haloalkyl, C3-10 cycloalkyl, C1-6 alkyl-C3-10 cycloalkyl, heterocycloalkyl, or C1-6 alkyl-(heterocycloalkyl);
each heterocycloalkyl is a 3 to 20 membered ring having 1 to 4 heteroatoms each independently N, O or S;
and
each heteroaryl is a 5 to 18 membered ring having 1 to 4 heteroatoms each independently N, O or S.

41 more elements

Facts

Application

18/413,767Filed 16 Jan 2024

Priority

23 Jun 2021

Published

20 Jun 2024

Term ends

Not estimatedThe source records don’t support an estimate.

Classification25 codes

C07D 413/14
Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms:…
A61K 31/517
Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim: ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
A61K 31/55
Having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins: having seven-membered rings, e.g. azelastine, pentylenetetrazole
A61K 31/553
Having seven-membered rings, e.g. azelastine, pentylenetetrazole: having at least one nitrogen and one oxygen as ring hetero atoms, e.g. loxapine,…

Family

Application63/213,893Us provisional application · filed 23 Jun 2021

Application17/845,469Continuation · filed 21 Jun 2022

Application18/413,767Continuation

US 11,932,634 B2Related patent

US 2023/0060004 A1Published application

US 2024/0199596 A1This patent

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