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US 2008/0076800 A1Published application
Benzene, Pyridine, and Pyridazine Derivatives
OwnerKenneth Huang, Thomas Barta +3inventors
InventorsKenneth Huang, Thomas Barta, Emilie Smith, Steven Hall, James Veal
Life of this patent
Estimating the term…
Abstract
Disclosed are compounds and pharmaceutically acceptable salts of Formula I wherein A, Q1, Q2, Q3, R3, R4, R5, RO, m, and p are as defined herein. Compounds of Formula I are useful in the treatment of diseases and/or conditions related to cell proliferation, such as cancer, inflammation, arthritis, angiogenesis, or the like. Also disclosed are pharmaceutical compositions comprising compounds of the invention and methods of treating the aforementioned conditions using such compounds.
Claims55
A compound of the formula
- or a pharmaceutically acceptable salt thereof, wherein
- p is 0, 1, 2, 3, 4, or 5;
- m is 0, 1, 2, 3, 4, or 5, provided that the sum of m and p is less than or equal to 5;
- each q is independently 0, 1, or 2;
- each R is independently halogen, cyano, nitro, C1-C6 alkyl, halo(C1-C6)alkyl, hydroxy, C1-C6 alkoxy, halo(C1-C6)alkoxy, amino, mono- or di-(C1-C6) alkylamino, carboxy, carboxamide, C3-C7 cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;
- each RC is independently halogen, cyano, nitro, —ORO, —N(RN)2, SRO, or —RN;
- each RN is independently —RN′, —C(O)RN′, —C(O)ORN′, —C(O)N(RN′)2, —S(O)RN′, or —S(O)2RN′ wherein
- each RN′ is independently hydrogen, C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C1-C10 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl (C1-C10)alkyl, heterocycloalkyl, heterocycloalkyl (C1-C10)alkyl, aryl, aryl (C1-C10)alkyl, heteroaryl, or heteroaryl(C1-C10)alkyl, wherein
- each RN′ is optionally substituted with from 1 to 4 R groups;
- each RO is independently —RN′, —C(O)RN′, —C(O)ORN′, or —C(O)N(RN′)2;
- R3 and R4 are independently (a) hydrogen, (b) halo, or (c) a C1-C15 alkyl group where up to six of the carbon atoms in said alkyl group are optionally replaced independently by R22, carbonyl, ethenyl, ethynyl or a moiety selected from N, O, or S(O)q, with the proviso that two O atoms, two S atoms, or an O and S atom are not immediately adjacent each other, wherein
- each R22 is independently (i) heteroaryl, (ii) aryl, (iii) saturated or unsaturated C3-C10 cycloalkyl, or (iv) saturated or unsaturated C2-C10 heterocycloalkyl, wherein
- each R22 is optionally substituted with 1 to 4 groups which are independently —R, oxo, —SH, —S(O)q—(C1-C6)alkyl, —S(O)q-aryl, —SO2NH2, —SO2NH—(C1-C6)alkyl, or —SO2NH-aryl;
- and
- each R22 is optionally fused to a C6-C10 aryl group, C5-C8 saturated cyclic group, or a C5-C10 heterocycloalkyl group;
- and
- each (c) is optionally substituted with —RC, —OR15, —SR15, or —N(R15)2, or —R22, wherein
- each R15 is independently —H, (C1-C10)alkyl, (C1-C10) haloalkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, or (C1-C10)alkyl-Z, wherein
- Z is —OR0 or —N(R30)2, wherein
- each R30 is independently —H or C1-C6 alkyl;
- or N(R30)2 represents pyrrolidinyl, piperidinyl, piperazinyl, azepanyl, 1,3- or 1,4-diazepanyl, or morpholinyl, each of which is optionally substituted with R;
- and
- or R3 and R4 together with the atoms to which they are attached form a 5-12 membered mono-, bi-, or tricyclic ring system fused to the ring containing Q1 and Q2, where the 5-12 membered ring is partially unsaturated or aromatic and optionally contains one or two of oxygen, S(O)q, nitrogen, or NR33 where R33 is hydrogen or C1-C6 alkyl;
- Q1, Q2, and Q3 are independently N or CRQ, with the proviso that at least one Q1, Q2, or Q3 is CRQ, wherein
- each RQ is independently hydrogen, halogen, —N(RN)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, aryl, or heteroaryl, or —R21, wherein each RQ is optionally substituted with from 1-4 R groups, wherein
- R21 is cyano, —C(O)OH, —C(O)—O(C1-C6alkyl), —C(X)N(R1)2, wherein
- each R1 is independently hydrogen, hydroxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, heteroaryl, aryl, C3-C8 cycloalkyl, heterocycloalkyl,
- wherein each R1 is optionally substituted with from 1-4 R groups;
- or both R1 together with the nitrogen to which they are attached, form a heterocycloalkyl;
- and
- X is ═O, ═S, ═NH, ═NOH, ═N—NH2, ═N—NH-aryl, ═N-=NH— (C1-C6 alkyl), or ═N—(C1-C6 alkoxy);
- A is a bond, O, S(O)q, N(RN), C(O), or CH(RC);
- and each R5 is independently RC.
30 more elements
Dependencies are inferred from the claim text.