US2007203161A1PendingUtilityA1
Compositions and methods for inhibition of the jak pathway
Est. expiryFeb 24, 2026(expired)· nominal 20-yr term from priority
Inventors:Ankush ArgadeArvinder SranDavid CarrollJeffrey CloughKin TsoSomasekhar BhamidipatiSambaiah ThotaRajinder SinghVanessa TaylorHui LiEsteban Masuda
A61P 35/00A61P 37/06A61P 43/00A61P 35/02C07D 405/12C07D 401/14C07D 403/12C07D 401/12C07D 417/12C07D 407/12C07D 239/48C07D 413/12C07D 413/14C07D 498/04A61K 31/505
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Claims
Abstract
The invention encompasses compounds having formula I and the compositions and methods using these compounds in the treatment of conditions in which modulation of the JAK pathway or inhibition of JAK kinases, particularly JAK3, are therapeutically useful.
Claims
exact text as granted — not AI-modified1 . A compound of the formula I:
a solvate, prodrug or pharmaceutically acceptable salt thereof; wherein:
X is selected from the group consisting of alkyl, substituted alkyl, alkoxy, substituted alkoxy, amino, substituted amino, carboxyl, carboxyl ester, cyano, halo, nitro, alkenyl, substituted alkenyl, alkynyl and substituted alkynyl;
Y is selected from the group consisting of hydrogen, alkyl substituted alkyl, amino, substituted amino, and halo;
R is selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl and substituted cycloalkyl;
ring A is selected from the group consisting of aryl, heteroaryl, cycloalkyl, cycloalkenyl and heterocyclic, wherein ring A is not indolyl or benzimidazolyl;
p is 0, 1, 2 or 3;
q is 1, 2 or 3 when ring A is a single ring, or q is 0, 1, 2, 3, 4, or 5 when ring A comprises multiple rings;
each R 2 independently is selected from the group consisting of alkyl, substituted alkyl, alkoxy, substituted alkoxy, amino, substituted amino, aryl, substituted aryl, aryloxy, substituted aryloxy, cycloalkyl, substituted cycloalkyl heteroaryl, substituted heteroaryl, heterocyclic, substituted heterocyclic, heterocyclyloxy, substituted carboxyl, carboxyl ester, hydroxyl, acylamino, aminosufonyl, alkynyl, substituted alkynyl, alkylthio, substituted alkylthio, aminocarbonyl, acyl, oxo, and halo;
each R 3 independently is selected from the group consisting of alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heterocyclic, substituted heterocyclic, halo, and aminosulfonyl; and
R 4 and R 5 independently are selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, alkoxy, cycloalkyl, substituted cycloalkyl, and acyl; or
R 4 and R 5 together with the nitrogen atom bound thereto, form a heterocyclic or substituted heterocyclic group;
provided that:
if q=0, then X is not bromo;
if ring A is cycloalkyl, then X is not bromo;
if q=2 and each of R 2 is methoxy, halo, trihalomethyl or trihalomethoxy, then R 4 and R 5 are not one hydrogen and one methyl;
if q=2 and R 2 is fluoro and methyl, then R is not substituted alkenyl; and
if ring A is phenyl, q=1 and R 2 is chloro, then R 4 and R 5 are not one hydrogen and one methyl.
2 . The compound of claim 1 , wherein Y is hydrogen.
3 . The compound of claim 1 , wherein X is hydrogen.
4 . The compound of claim 1 , wherein ring A is selected from the group consisting of:
wherein Q is sulfur, oxygen or carbon, and R 1 is hydrogen, alkyl, substituted alkyl, alkynyl, or acyl,
wherein Q is oxygen or nitrogen,
wherein Q is nitrogen or carbon,
wherein Q is oxygen or nitrogen, and
5 . The compound of claim 1 , wherein
ring A is phenyl; R is hydrogen; X is halo, cyano or alkyl; and q is 1 or 2.
6 . A compound selected from the group consisting of:
I-1: N4-(3-Acetylamino-4-hydroxyphenyl)-N2-(3-aminosulfonylphenyl)-5-fluoro-2,4-pyrimidinediamine;
I-2: N4-(3-Acetylamino-4-hydroxyphenyl)-N2-(3-aminosulfonyl-4-methylphenyl)-5-fluoro-2,4-pyrimidinediamine;
I-3: N4-(3-Acetylamino-4-hydroxyphenyl)-N2-(4-aminosulfonylphenyl)-5-fluoro-2,4-pyrimidinediamine;
I-4: N4-(3-Chloro-4-methoxyphenyl)-N2-(3-N,N-dimethylaminosulfonylphenyl)-5-fluoro-2,4-pyrimidinediamine;
I-5: N4-(3-Chloro-4-methoxyphenyl)-N2-(4-N,N-dimethylaminosulfonylphenyl)-5-fluoro-2,4-pyrimidinediamine;
I-6: N2-(3-Aminosulfonyl-4-methylphenyl)-5-fluoro-N4-[4-(prop-2-ynyloxy)phenyl]-2,4-pyrimidinediamine;
I-7: N2-(3-Aminosulfonyl-4-chlorophenyl)-5-fluoro-N4-[4-(prop-2-ynyloxy)phenyl]-2,4-pyrimidinediamine;
I-8: 5-Fluoro-N2-(4-methyl-3-propionylaminosulfonylphenyl)-N4-[4-(prop-2-ynyloxy)phenyl]-2,4-pyrimidinediamine;
I-9: N2-(3-Aminosulfonyl-4-methylphenyl)-5-fluoro-N4-[3-(prop-2-ynyloxy)phenyl]-2,4-pyrimidinediamine;
I-10: N2-(3-Aminosulfonyl-4-methylphenyl)-5-fluoro-N4-[3-methyl-4-(prop-2-ynyloxy)phenyl]-2,4-pyrimidinediamine;
I-11: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-[3-chloro-4-(prop-2-ynyloxy)phenyl]-5-fluoro-2,4-pyrimidinediamine;
I-12: N2-(3-Aminosulfonyl-4-methylphenyl)-5-fluoro-N4-[3-fluoro-4-(prop-2-ynyloxy)phenyl]-2,4-pyrimidinediamine;
I-13: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-[4-(but-2-ynyloxy)phenyl]-5-fluoro-2,4-pyrimidinediamine;
I-14 N2-(4-methyl-3-propionylaminosulfonylphenyl)-5-fluoro-N4-[4-(prop-2-ynyloxy)phenyl]-2,4-pyrimidinediamine;
I-15: N2-[3-Aminosulfonyl-4-(2-propyl)phenyl]-5-fluoro-N4-[4-(prop-2-ynyloxy)phenyl]-2,4-pyrimidinediamine;
I-16: N2-(3-Aminosulfonyl-4-methylphenyl)-5-fluoro-N4-[4-(prop-2-ynylamino)phenyl]-2,4-pyrimidinediamine;
I-17: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-{4-[bis(prop-2-ynyl)amino]phenyl}-5-fluoro-2,4-pyrimidinediamine;
I-18: 5-Fluoro-N2-(4-methyl-3-methylaminosulfonylphenyl)-N4-[4-(prop-2-ynyloxy)phenyl]-2,4-pyrimidinediamine;
I-19: 5-Fluoro-N2-{[4-methyl-3-((1-methylpiperidin-4-yl)aminosulfonyl)]phenyl}-N4-[4-(prop-2-ynyloxy)phenyl]-2,4-pyrimidinediamine;
I-20: N2-[3-Aminosulfonyl-4-(1-methylpiperazin-4-yl)phenyl]-5-fluoro-N4-[4-(prop-2-ynyloxy)phenyl]-2,4-pyrimidinediamine;
I-21: N2-(3-Aminosulfonyl-4-methylphenyl)-5-fluoro-N4-{4-[(prop-2-ynyloxy)carbonylaminomethyl]phenyl}-2,4-pyrimidinediamine;
I-22: N2-(3-Aminosulfonylphenyl)-5-fluoro-N4-{4-[(prop-2-ynyloxy)carbonylaminomethyl]phenyl}-2,4-pyrimidinediamine;
I-23: N2-(3-Aminosulfonylphenyl)-5-fluoro-N4-[4-(prop-2-ynylaminosulfonyl)phenyl]-2,4-pyrimidinediamine;
I-24: N2-(3-Aminosulfonyl-4-methylphenyl)-5-fluoro-N4-[4-(prop-2-ynylaminosulfonyl)phenyl]-2,4-pyrimidinediamine;
I-25: N2-(4-Aminosulfonylphenyl)-5-fluoro-N4-[4-(prop-2-ynylaminosulfonyl)phenyl]-2,4-pyrimidinediamine;
I-26 5-Fluoro-N2-[3-(prop-2-ynylaminosulfonyl)phenyl]-N4-[4-(prop-2-ynyloxy)phenyl]-2,4-pyrimidinediamine;
I-27: N2-(3-Aminosulfonyl-4-methylphenyl)-5-fluoro-N4-[3-(prop-2-ynylaminosulfonyl)phenyl]-2,4-pyrimidinediamine;
I-28: N2-(4-Aminosulfonylphenyl)-5-fluoro-N4-[3-(prop-2-ynylaminosulfonyl)phenyl]-2,4-pyrimidinediamine;
I-29: N2-(3-Aminosulfonylphenyl)-5-fluoro-N4-[3-(prop-2-ynylaminosulfonyl)phenyl]-2,4-pyrimidinediamine;
I-30: N2-(3-Aminosulfonyl-4-methylphenyl)-5-methyl-N4-[4-(2-propynyloxy)phenyl]-2,4-pyrimidinediamine;
I-31: N2-(3-Aminosulfonylphenyl)-5-methyl-N4-[4-(2-propynyloxy)phenyl]-2,4-pyrimidinediamine;
I-32: N2-(4-Aminosulfonylphenyl)-5-methyl-N4-[4-(2-propynyloxy)phenyl]-2,4-pyrimidinediamine;
I-33: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-[4-(2-propynyloxy)phenyl]-5-trifluoromethyl-2,4-pyrimidinediamine;
I-34: N2-(3-Aminosulfonyl-4-methylphenyl)-5-chloro-N4-[4-(2-propynyloxy)phenyl]-2,4-pyrimidinediamine;
I-35: N2-(4-Aminosulfonylphenyl)-5-chloro-N4-[4-(2-propynyloxy)phenyl]-2,4-pyrimidinediamine;
I-36: N2-(3-Aminosulfonylphenyl)-5-chloro-N4-[4-(2-propynyloxy)phenyl]-2,4-pyrimidinediamine;
I-37: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-[4-(3-butynyloxy)phenyl]-5-fluoro-2,4-pyrimidinediamine;
I-38: N2-(4-Aminosulfonylphenyl)-N4-[4-(3-butynyloxy)phenyl]-5-fluoro-2,4-pyrimidinediamine;
I-39: N2-(3-Aminosulfonylphenyl)-N4-[4-(3-butynyloxy)phenyl]-5-fluoro-2,4-pyrimidinediamine;
I-40: N2-(3-Aminosulfonyl-4-methylphenyl)-5-cyano-N4-[4-(2-propynyloxy)phenyl]-2,4-pyrimidinediamine;
I-41: N2-(3-Aminosulfonylphenyl)-5-cyano-N4-[4-(2-propynyloxy)phenyl]-2,4-pyrimidinediamine;
I-42: N2-(4-Aminosulfonylphenyl)-5-cyano-N4-[4-(2-propynyloxy)phenyl]-2,4-pyrimidinediamine;
I-43: N2-(3-Aminosulfonylphenyl)-5-fluoro-N4-[4-(2-propynyloxy)phenyl]-2,4-pyrimidinediamine;
I-44: N2-(4-Aminosulfonylphenyl)-5-fluoro-N4-[4-(2-propynyloxy)phenyl]-2,4-pyrimidinediamine;
I-45: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-[4-(3-butynyl)phenyl]-5-fluoro-2,4-pyrimidinediamine;
I-46: N2-(3-Aminosulfonylphenyl)-N4-[4-(2-propynyloxy)phenyl]-5-trifluoromethyl-2,4-pyrimidinediamine;
I-47: N2-(4-Aminosulfonylphenyl)-N4-[4-(2-propynyloxy)phenyl]-5-trifluoromethyl-2,4-pyrimidinediamine;
I-48: N2-(3-Aminosulfonyl-4-methylphenyl)-5-cyclopropyl-N4-[4-(2-propynyloxy)phenyl]-2,4-pyrimidinediamine;
I-49: 5-Fluoro-N2-[4-methyl-3-(N-propionylaminosulfonyl)phenyl]-N4-[4-(2-propynyloxy)phenyl]-2,4-pyrimidinediamine Potassium Salt;
I-50: 5-Fluoro-N2-[4-methyl-3-(N-propionylaminosulfonyl)phenyl]-N4-[4-(2-propynyloxy)phenyl]-2,4-pyrimidinediamine Calcium Salt;
I-51: N2-(4-Aminosulfonylphenyl)-N4-[4-(3-butynyl)phenyl]-5-fluoro-2,4-pyrimidinediamine;
I-52: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-[4-((1-benzyl-1H-1,2,3-triazol-4-yl)methoxy)phenyl]-5-fluoro-2,4-pyrimidinediamine;
I-53: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-[4-((1-cyclohexyl-1H-1,2,3-triazol-4-yl)methoxy)phenyl]-5-fluoro-2,4-pyrimidinediamine;
I-54: 5-Fluoro-N2-[3-(N-methoxyaminosulfonyl)phenyl]-N4-[4-(2-propynyloxy)phenyl]-2,4-pyrimidinediamine;
I-55: 5-Fluoro-N2-[3-((2-methyl-2-propoxy)aminosulfonyl)phenyl]-N4-[4-(2-propynyloxy)phenyl]-2,4-pyrimidinediamine;
I-56: 5-Fluoro-N2-[4-methyl-3-(N-propionylaminosulfonyl)phenyl]-N4-[4-(2-propynyloxy)phenyl]-2,4-pyrimidinediamine Arginine Salt;
I-57: 5-Fluoro-N2-[4-methyl-3-(N-propionylaminosulfonyl)phenyl]-N4-[4-(2-propynyloxy)phenyl]-2,4-pyrimidinediamine Choline Salt;
I-58: N2-(3-Aminosulfonylphenyl)-N4-(ethoxycarbonylmethyl)-N4-(3-chloro-4-methoxyphenyl)-5-nitro-2,4-pyrimidinediamine;
I-59: N2-(3-Aminosulfonylphenyl)-N4-[4-(1H-benzimidazol-2-yl)phenyl]-5-fluoro-2,4-pyrimidinediamine;
I-60: N2-(4-Aminosulfonylphenyl)-N4-[4-(1H-benzimidazol-2-yl)phenyl]-5-fluoro-2,4-pyrimidinediamine;
I-61: N2-(3-Aminosulfonylphenyl)-N4-[4-(1H-benzimidazol-2-yl)phenyl]-5-methyl-2,4-pyrimidinediamine;
I-62: N2-(4-Aminosulfonylphenyl)-N4-[4-(1H-benzimidazol-2-yl)phenyl]-5-methyl-2,4-pyrimidinediamine;
I-63: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-[4-(1H-benzimidazol-2-yl)phenyl]-5-methyl-2,4-pyrimidinediamine;
I-64: N2-(3-Aminosulfonylphenyl)-N4-[4-(1H-benzimidazol-2-ylmethyl)phenyl]-5-fluoro-2,4-pyrimidinediamine;
I-65: N2-(4-Aminosulfonylphenyl)-N4-[4-(1H-benzimidazol-2-ylmethyl)phenyl]-5-fluoro-2,4-pyrimidinediamine;
I-66: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-[4-(1H-benzimidazol-2-ylmethyl)phenyl]-5-fluoro-2,4-pyrimidinediamine;
I-67: N2-(3-Aminosulfonylphenyl)-N4-[4-(1H-benzimidazol-2-ylmethyl)phenyl]-5-methyl-2,4-pyrimidinediamine;
I-68: N2-(4-Aminosulfonylphenyl)-N4-[4-(1H-benzimidazol-2-ylmethyl)phenyl]-5-methyl-2,4-pyrimidinediamine;
I-69: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-[4-(1H-benzimidazol-2-ylmethyl)phenyl]-5-methyl-2,4-pyrimidinediamine;
I-70: N2-(3-Aminosulfonylphenyl)-N4-[3-(1H-benzimidazol-2-ylmethyl)phenyl]-5-fluoro-2,4-pyrimidinediamine;
I-71: N2-(4-Aminosulfonylphenyl)-N4-[3-(1H-benzimidazol-2-ylmethyl)phenyl]-5-fluoro-2,4-pyrimidinediamine;
I-72: N2-(3-Aminosulfonylphenyl)-N4-[3-(1H-benzimidazol-2-ylmethyl)phenyl]-5-methyl-2,4-pyrimidinediamine;
I-73: N2-(4-Aminosulfonylphenyl)-N4-[3-(1H-benzimidazol-2-ylmethyl)phenyl]-5-methyl-2,4-pyrimidinediamine;
I-74: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-[3-(4-cyanophenyl)phenyl]-5-fluoro-2,4-pyrimidinediamine;
I-75: N2-(3-Aminosulfonylphenyl)-N4-[4-(3-cyanophenyl)phenyl]-5-fluoro-2,4-pyrimidinediamine;
I-76: N2-(4-Aminosulfonylphenyl)-N4-[3-(4-cyanophenyl)phenyl]-5-fluoro-2,4-pyrimidinediamine;
I-77: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-[4-(3-cyanophenyl)phenyl]-5-fluoro-2,4-pyrimidinediamine;
I-78: N4-[4-(3-Cyanophenyl)phenyl]-5-fluoro-N2-[4-methyl-3-(N-methylaminosulfonyl)phenyl]-2,4-pyrimidinediamine;
I-79: N2-(3-Aminosulfonylphenyl)-N4-[3-(4-cyanophenyl)phenyl]-5-fluoro-2,4-pyrimidinediamine;
I-80: N4-[3-(4-Cyanophenyl)phenyl]-5-fluoro-N2-[4-methyl-3-(N-methylaminosulfonyl)phenyl]-2,4-pyrimidinediamine;
I-81: N2-(4-Aminosulfonylphenyl)-N4-[4-(3-cyanophenyl)phenyl]-5-fluoro-2,4-pyrimidinediamine;
I-82: N2-(3-Aminosulfonylphenyl)-5-methyl-N4-[4-(4-pyridinylmethyl)phenyl]-2,4-pyrimidinediamine;
I-83: N2-(3-Aminosulfonyl-4-methylphenyl)-5-methyl-N4-[4-(4-pyridinylmethyl)phenyl]-2,4-pyrimidinediamine;
I-84: 5-Methyl-N2-[4-methyl-3-(N-methylaminosulfonyl)phenyl]-N4-[4-(4-pyridinylmethyl)phenyl]-2,4-pyrimidinediamine;
I-85: N2-(4-Aminosulfonylphenyl)-5-methyl-N4-[4-(4-pyridinylmethyl)phenyl]-2,4-pyrimidinediamine;
I-86: N2-(4-Aminosulfonylphenyl)-5-methyl-N4-[4-(2-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine Hydrogen Chloride Salt;
I-87: 5-Fluoro-N2-[4-methyl-3-(N-methylaminosulfonyl)phenyl]-N4-[4-(3-pyridinylmethylenethio)phenyl]-2,4-pyrimidinediamine;
I-88: N2-(3-Aminosulfonyl-4-methylphenyl)-5-fluoro-N4-[4-(3-pyridinylmethyl)phenyl]-2,4-pyrimidinediamine;
I-89: N2-(4-Aminosulfonylphenyl)-5-methyl-N4-[4-(3-pyridinylmethyl)phenyl]-2,4-pyrimidinediamine;
I-90: 5-Methyl-N2-[4-(N-propionylaminosulfonyl)phenyl]-N4-[4-(2-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
I-91: 5-Methyl-N2-[4-(N-propionylaminosulfonyl)phenyl]-N4-[4-(2-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine Sodium Salt;
I-92: N2-(3-Aminosulfonylphenyl)-5-fluoro-N4-[4-(3-pyridinylmethyl)phenyl]-2,4-pyrimidinediamine;
I-93: N2-(3-Aminosulfonylphenyl)-5-methyl-N4-[4-(3-pyridinylmethyl)phenyl]-2,4-pyrimidinediamine;
I-94: N2-(3-Aminosulfonyl-4-methylphenyl)-5-fluoro-N4-[4-(3-pyridinylmethylenethio)phenyl]-2,4-pyrimidinediamine;
I-95: N2-(4-Aminosulfonylphenyl)-5-fluoro-N4-[4-(3-pyridinylmethylenethio)phenyl]-2,4-pyrimidinediamine;
I-96: N2-(3-Aminosulfonylphenyl)-5-methyl-N4-[4-(3-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
I-97: N2-(3-Aminosulfonyl-4-methylphenyl)-5-methyl-N4-[4-(3-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
I-98: 5-Methyl-N2-[4-methyl-3-(N-methylaminosulfonyl)phenyl]-N4-[4-(3-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
I-99: N2-(4-Aminosulfonylphenyl)-5-methyl-N4-[4-(3-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
I-100: N2-(3-Aminosulfonylphenyl)-5-methyl-N4-[4-(4-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
I-101: 5-Methyl-N2-[4-(N-propionylaminosulfonyl)phenyl]-N4-[4-(2-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine Hydrogen Chloride Salt;
I-102: N2-(3-Aminosulfonyl-4-methylphenyl)-5-methyl-N4-[4-(4-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
I-103: 5-Methyl-N2-[4-methyl-3-(N-methylaminosulfonyl)phenyl]-N4-[4-(5-pyrimidinyloxy)phenyl]-2,4-pyrimidinediamine;
I-104: N2-(3-Aminosulfonylphenyl)-N4-(4-ethynylphenyl)-5-methyl-2,4-pyrimidinediamine;
I-105: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-(4-ethynylphenyl)-5-methyl-2,4-pyrimidinediamine;
I-106: N2-(4-Aminosulfonylphenyl)-N4-(4-ethynylphenyl)-5-methyl-2,4-pyrimidinediamine;
I-107: N2-(3-Aminosulfonylphenyl)-5-methyl-N4-[4-(5-pyrimidinyloxy)phenyl]-2,4-pyrimidinediamine;
I-108: N4-(4-Ethynylphenyl)-5-methyl-N2-[4-methyl-3-(N-methylaminosulfonyl)phenyl]-2,4-pyrimidinediamine;
I-109: N2-(3-Aminosulfonylphenyl)-N4-[4-(2-pyridinylmethyleneoxy)phenyl]-5-trifluoromethyl-2,4-pyrimidinediamine;
I-110: N2-(4-Aminosulfonylphenyl)-5-methyl-N4-[4-(5-pyrimidinyloxy)phenyl]-2,4-pyrimidinediamine;
I-111: N2-(4-Aminosulfonylphenyl)-5-methyl-N4-[4-(4-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
I-112: N2-(4-Aminosulfonylphenyl)-N4-[4-(2-pyridinylmethyleneoxy)phenyl]-5-trifluoromethyl-2,4-pyrimidinediamine;
I-113: N2-[3-(N,N-Dimethylaminosulfonyl)phenyl]-5-methyl-N4-[4-(3-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
I-114: N2-[4-(N,N-Dimethylaminosulfonyl)phenyl]-5-methyl-N4-[4-(3-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
I-115: N2-[4-(N,N-Dimethylaminosulfonyl)phenyl]-5-fluoro-N4-[4-(2-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
I-116: N2-(3-Aminosulfonyl-4-methylphenyl)-5-methyl-N4-[4-(5-pyrimidinyloxy)phenyl]-2,4-pyrimidinediamine;
I-117: N2-[3-(N-Cyclopropylaminosulfonyl)phenyl]-5-methyl-N4-[4-(2-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
I-118: N2-(4-Aminosulfonylphenyl)-N4-(3-ethynylphenyl)-5-methyl-2,4-pyrimidinediamine;
I-119: N2-[4-(N-Cyclopropylaminosulfonyl)phenyl]-5-methyl-N4-[4-(2-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
I-120: N2-[3-(N-Cyclopropylaminosulfonyl)phenyl]-5-methyl-N4-[4-(3-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
I-121: N2-[3-(N-Cyclopropylaminosulfonyl)phenyl]-5-methyl-N4-[4-(5-pyrimidinyloxy)phenyl]-2,4-pyrimidinediamine;
I-122: N2-[4-(N-Cyclopropylaminosulfonyl)phenyl]-5-methyl-N4-[4-(5-pyrimidinyloxy)phenyl]-2,4-pyrimidinediamine;
I-123: N2-[4-(N-Cyclopropylaminosulfonyl)phenyl]-5-methyl-N4-[4-(3-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
I-124: N2-(3-Aminosulfonylphenyl)-N4-(3-ethynylphenyl)-5-methyl-2,4-pyrimidinediamine;
I-125: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-(3-ethynylphenyl)-5-methyl-2,4-pyrimidinediamine;
I-126: N4-(3-Ethynylphenyl)-5-methyl-N2-[4-methyl-3-(N-methylaminosulfonyl)phenyl]-2,4-pyrimidinediamine;
I-127: N2-[3-(N,N-Dimethylaminosulfonyl)phenyl]-5-fluoro-N4-[4-(2-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
I-128: N2-(4-Aminosulfonylphenyl)-5-cyclopropyl-N4-[4-(2-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
I-129: N2-(3-Aminosulfonylphenyl)-5-cyclopropyl-N4-[4-(2-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
I-130: N2-[3-(N-Cyclopropylaminosulfonyl)phenyl]-5-methyl-N4-[4-(3-pyridinylmethyl)phenyl]-2,4-pyrimidinediamine;
I-131: N2-[3-N-(Cyclopropylaminosulfonyl)phenyl]-5-fluoro-N4-[4-(2-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
I-132: N2-[4-(N-Cyclopropylaminosulfonyl)phenyl]-5-fluoro-N4-[4-(2-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
I-133: N2-[3-(N-Cyclopropylaminosulfonyl)phenyl]-5-methyl-N4-[4-(4-pyridinylmethyl)phenyl]-2,4-pyrimidinediamine;
I-134: N2-[4-(N-Cyclopropylaminosulfonyl)phenyl]-5-methyl-N4-[4-(4-pyridinylmethyl)phenyl]-2,4-pyrimidinediamine;
I-135: N2-[4-(N-Cyclopropylmethylaminosulfonyl)phenyl]-5-methyl-N4-[4-(2-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
I-136: N2-[4-(N-Cyclopropylmethylaminosulfonyl)phenyl]-5-methyl-N4-[4-(3-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
I-137: N2-[3-(N-Cyclopropylmethylaminosulfonyl)phenyl]-5-methyl-N4-[4-(2-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
I-138: N2-[3-(N-Cyclopropylmethylaminosulfonyl)phenyl]-5-methyl-N4-[4-(3-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
I-139: N2-[4-(N-Cyclopropylmethylaminosulfonyl)phenyl]-5-methyl-N4-[4-(5-pyrimidinyloxy)phenyl]-2,4-pyrimidinediamine;
I-140: N2-[3-(N-Cyclopropyl-N-propionylaminosulfonyl)phenyl]-5-methyl-N4-[4-(2-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
I-141: N2-[3-(N-Cyclopropyl-N-propionylaminosulfonyl)phenyl]-5-methyl-N4-[4-(2-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine Hydrogen Chloride Salt;
I-142: 5-Chloro-N2-[3-(N-cyclopropylaminosulfonyl)phenyl]-N4-[4-(2-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
I-143: 5-Chloro-N2-[4-(N-cyclopropylmethylaminosulfonyl)phenyl]-N4-[4-(2-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
I-144: 5-Chloro-N2-[4-(N-cyclopropylaminosulfonyl)phenyl]-N4-[4-(2-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
I-145: 5-Chloro-N2-[3-(N-cyclopropylmethylaminosulfonyl)phenyl]-N4-[4-(2-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
I-146: N2-(4-Aminosulfonylphenyl)-5-methyl-N4-[4-(2-pyridinylmethylenethio)phenyl]-2,4-pyrimidinediamine;
I-147: N2-(3-Aminosulfonylphenyl)-5-methyl-N4-[4-(2-pyridinylmethylenethio)phenyl]-2,4-pyrimidinediamine;
I-148: N2-(3-Aminosulfonyl-4-methylphenyl)-5-methyl-N4-[4-(2-pyridinylmethylenethio)phenyl]-2,4-pyrimidinediamine;
I-149: N2-[3-(N-Cyclopropylaminosulfonyl)phenyl]-5-methyl-N4-[4-(2-pyridinylmethylenethio)phenyl]-2,4-pyrimidinediamine;
I-150: N2-[4-(N-Cyclopropylaminosulfonyl)phenyl]-5-methyl-N4-[4-(2-pyridinylmethylenethio)phenyl]-2,4-pyrimidinediamine;
I-151: N2-[3,5-Bis(aminosulfonyl)phenyl]-N4-[4-(2-cyanoethyl)phenyl]-5-fluoro-2,4-pyrimidinediamine;
I-152: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-[3-(2-cyanoethyl)-5-trifluoromethylphenyl]-5-fluoro-2,4-pyrimidinediamine;
I-153: N2-(3-Aminosulfonylphenyl)-N4-[3-(2-cyanoethyl)-5-trifluoromethylphenyl]-5-fluoro-2,4-pyrimidinediamine;
I-154: N2-(4-Aminosulfonylphenyl)-N4-[3-(2-cyanoethyl)-5-trifluoromethylphenyl]-5-fluoro-2,4-pyrimidinediamine;
I-155: N4-[4-(2-Cyanoethyl)phenyl]-5-methyl-N2-[4(N-propionylaminosulfonyl)phenyl]-2,4-pyrimidinediamine;
I-156: N4-[4-(2-Cyanoethyl)phenyl]-5-methyl-N2-[4-(N-propionylaminosulfonyl)phenyl]-2,4-pyrimidinediamine Sodium Salt;
I-157: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-[4-(2-cyanoethyl)-3-methylphenyl]-5-methyl-2,4-pyrimidinediamine;
I-158: N2-(3-Aminosulfonylphenyl)-N4-[4-(2-cyanoethyl)-3-methylphenyl]-5-methyl-2,4-pyrimidinediamine;
I-159: N2-(4-Aminosulfonylphenyl)-N4-[4-(2-cyanoethyl)-3-methylphenyl]-5-methyl-2,4-pyrimidinediamine;
I-160: N2-(3-Aminosulfonyl-4-methylphenyl)-5-fluoro-N4-[4-((1-methyl-1H-pyrazol-3-yl)aminocarbonylmethylene)phenyl]-2,4-pyrimidinediamine;
I-161: N2-(3-Aminosulfonylphenyl)-N4-(4-N,N-dimethylaminosulfonylphenyl)-5-fluoro-2,4-pyrimidinediamine;
I-162: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-(4-N,N-dimethylaminosulfonylphenyl)-5-fluoro-2,4-pyrimidinediamine;
I-163: N2-(4-Aminosulfonylphenyl)-5-chloro-N4-[4-(2-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
I-164: N2-(3-Aminosulfonylphenyl)-5-chloro-N4-[4-(2-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
I-165: N2-(3-Aminosulfonyl-4-methylphenyl)-5-chloro-N4-[4-(2-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
I-166: N2-(3-(N-butyrylsulfamoyl)-4-methylphenyl)-5-fluoro-N4-[4-(2-propynyloxy)phenyl]-2,4-pyrimidinediamine;
I-167: N2-(3-(N-isobutyrylsulfamoyl)-4-methylphenyl)-5-fluoro-N4-[4-(2-propynyloxy)phenyl]-2,4-pyrimidinediamine;
I-168: N2-(3-(N-butyrylsulfamoyl)-4-methylphenyl)-5-fluoro-N4-[4-(2-propynyloxy)phenyl]-2,4-pyrimidinediamine sodium salt;
I-169: N2-(3-(N-isobutyrylsulfamoyl)-4-methylphenyl)-5-fluoro-N4-[4-(2-propynyloxy)phenyl]-2,4-pyrimidinediamine sodium salt;
I-170: N2-(3-(N-hexanoylsulfamoyl)-4-methylphenyl)-5-fluoro-N4-[4-(2-propynyloxy)phenyl]-2,4-pyrimidinediamine;
I-171: N2-(3-(N-pentanoylsulfamoyl)-4-methylphenyl)-5-fluoro-N4-[4-(2-propynyloxy)phenyl]-2,4-pyrimidinediamine;
I-172: N2-(3-(N-hexanoylsulfamoyl)-4-methylphenyl)-5-fluoro-N4-[4-(2-propynyloxy)phenyl]-2,4-pyrimidinediamine sodium salt;
I-173: N2-(3-(N-pentanoylsulfamoyl)-4-methylphenyl)-5-fluoro-N4-[4-(2-propynyloxy)phenyl]-2,4-pyrimidinediamine sodium salt;
II-1: N2-(3-Aminosulfonyl-4-methylphenyl)-5-methyl-N4-(3-oxo-2H,4H-benzo[1,4]thiazin-6-yl)-2,4-pyrimidinediamine;
II-2: N2-(3-Aminosulfonylphenyl)-5-methyl-N4-(3-oxo-2H,4H-benzo[1,4]thiazin-6-yl)-2,4-pyrimidinediamine;
II-3: N2-(4-Aminosulfonylphenyl)-5-methyl-N4-(3-oxo-2H,4H-benzo[1,4]thiazin-6-yl)-2,4-pyrimidinediamine;
II-4: N2-(3-Aminosulfonyl-4-methylphenyl)-5-methyl-N4-(4-methyl-3-oxo-2H-benzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-5: N2-(3-Aminosulfonylphenyl)-5-methyl-N4-(4-methyl-3-oxo-2H-benzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-6: N2-(4-Aminosulfonylphenyl)-5-methyl-N4-(4-methyl-3-oxo-2H-benzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-7: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-(4-ethyl-3-oxo-2H-benzo[1,4]oxazin-6-yl)-5-fluoro-2,4-pyrimidinediamine;
II-8: N2-(3-Aminosulfonylphenyl)-N4-(4-ethyl-3-oxo-2H-benzo[1,4]oxazin-6-yl)-5-fluoro-pyrimidinediamine;
II-9: N2-(4-Aminosulfonylphenyl)-N4-(4-ethyl-3-oxo-2H-benzo[1,4]oxazin-6-yl)-5-fluoro-2,4-pyrimidinediamine;
II-10: N2-(3-Aminosulfonylphenyl)-N4-(4-ethyl-3-oxo-2H-benzo[1,4]thiazin-6-yl)-5-fluoro-2,4-pyrimidinediamine;
II-11: Racemic-N4-(2-aminocarbonyl-2-methyl-3-oxo-4H-benzo[1,4]oxazin-6-yl)-N2-(3-Aminosulfonyl-4-methylphenyl)-5-fluoro-2,4-pyrimidinediamine;
II-12: N2-(4-Aminosulfonylphenyl)-N4-(4-ethyl-3-oxo-2H-benzo[1,4]thiazin-6-yl)-5-fluoro-2,4-pyrimidinediamine;
II-13: 5-Methyl-N4-(4-methyl-3-oxo-2H-benzo[1,4]thiazin-6-yl)-N2-[4-(N-propionylaminosulfonyl)phenyl]-2,4-pyrimidinediamine;
II-14: N2-(3-Aminosulfonyl-4-methylphenyl)-5-methyl-N4-[3-oxo-4-(2-propynyl)-2H-benzo[1,4]thiazin-6-yl]-2,4-pyrimidinediamine;
II-15: N2-(3-Aminosulfonylphenyl)-5-methyl-N4-[3-oxo-4-(2-propynyl)-2H-benzo[1,4]thiazin-6-yl]-2,4-pyrimidinediamine;
II-16: N2-(4-Aminosulfonylphenyl)-5-methyl-N4-[3-oxo-4-(2-propynyl)-2H-benzo[1,4]thiazin-6-yl]-2,4-pyrimidinediamine;
II-17: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-(4-ethyl-3-oxo-2H-benzo[1,4]thiazin-6-yl)-5-methyl-2,4-pyrimidinediamine;
II-18: N2-(3-Aminosulfonylphenyl)-N4-(4-ethyl-3-oxo-2H-benzo[1,4]thiazin-6-yl)-5-methyl-2,4-pyrimidinediamine;
II-19: N2-(4-Aminosulfonylphenyl)-5-methyl-N4-(4-ethyl-3-oxo-2H-benzo[1,4]thiazin-6-yl)-5-methyl-2,4-pyrimidinediamine;
II-20: N2-(4-Aminosulfonylphenyl)-5-methyl-N4-(3-oxo-4-propyl-2H-benzo[1,4]thiazin-6-yl)-2,4-pyrimidinediamine;
II-21: N2-(3-Aminosulfonylphenyl)-5-methyl-N4-(3-oxo-4-propyl-2H-benzo[1,4]thiazin-6-yl)-2,4-pyrimidinediamine;
II-22: N2-(3-Aminosulfonyl-4-methylphenyl)-5-methyl-N4-(3-oxo-4-propyl-2H-benzo[1,4]thiazin-6-yl)-2,4-pyrimidinediamine;
II-23: N2-(4-Aminosulfonylphenyl)-5-bromo-N4-(4-methyl-3-oxo-2H-benzo[1,4]thiazin-6-yl)-2,4-pyrimidinediamine;
II-24: N2-[3-(N-Ethylaminosulfonyl)-4-methylphenyl]-5-methyl-N4-(3-oxo-2H,4H-benzo[1,4]thiazin-6-yl)-2,4-pyrimidinediamine;
II-25: N2-[3-(N-Ethylaminosulfonyl)-4-methylphenyl]-5-methyl-N4-(3-oxo-2H,4H-benzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-26: N2-[3-(N-Ethylaminosulfonyl)-4-methylphenyl]-5-methyl-N4-(4-methyl-3-oxo-2H-benzo[1,4]thiazin-6-yl)-2,4-pyrimidinediamine;
II-27: N2-[3-(N-Ethylaminosulfonyl)-4-methylphenyl]-N4-(4-ethyl-3-oxo-2H-benzo[1,4]thiazin-6-yl)-5-methyl-2,4-pyrimidinediamine;
II-28: N2-[3-(N-Ethylaminosulfonyl)-4-methylphenyl]-5-methyl-N4-(3-oxo-4-propyl-2H-benzo[1,4]thiazin-6-yl)-2,4-pyrimidinediamine;
II-29: N2-[3-(N-Ethylaminosulfonyl)-4-methylphenyl]-5-methyl-N4-(3-oxo-4-(2-propynyl)-2H-benzo[1,4]thiazin-6-yl)-2,4-pyrimidinediamine;
II-30: N2-[3-(N-Ethylaminosulfonyl)-4-methylphenyl]-5-methyl-N4-(4-methyl-3-oxo-2H-benzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-31: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-(4-butyl-3-oxo-2H-benzo[1,4]thiazin-6-yl)-5-methyl-2,4-pyrimidinediamine;
II-32: N2-(4-Aminosulfonylphenyl)-5-fluoro-N4-(3-oxo-4-propyl-2H-benzo[1,4]thiazin-6-yl)-2,4-pyrimidinediamine;
II-33: N2-(3-Aminosulfonylphenyl)-5-fluoro-N4-(3-oxo-4-propyl-2H-benzo[1,4]thiazin-6-yl)-2,4-pyrimidinediamine;
II-34: N2-(3-Aminosulfonyl-4-methylphenyl)-5-fluoro-N4-(3-oxo-4-propyl-2H-benzo[1,4]thiazin-6-yl)-2,4-pyrimidinediamine;
II-35: N2-(3-Aminosulfonylphenyl)-5-chloro-N4-(4-methyl-3-oxo-2H-benzo[1,4]thiazin-6-yl)-2,4-pyrimidinediamine;
II-36: N2-(3-Aminosulfonyl-4-methylphenyl)-5-chloro-N4-(4-methyl-3-oxo-2H-benzo[1,4]thiazin-6-yl)-2,4-pyrimidinediamine;
II-37: N2-(4-Aminosulfonylphenyl)-N4-(4-butyl-3-oxo-2H-benzo[1,4]thiazin-6-yl)-5-fluoro-2,4-pyrimidinediamine;
II-38: N2-(3-Aminosulfonylphenyl)-N4-(4-butyl-3-oxo-2H-benzo[1,4]thiazin-6-yl)-5-fluoro-2,4-pyrimidinediamine;
II-39: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-(4-butyl-3-oxo-2H-benzo[1,4]thiazin-6-yl)-5-fluoro-2,4-pyrimidinediamine;
II-40: N2-(3-Aminosulfonylphenyl)-N4-(4-butyl-3-oxo-2H-benzo[1,4]thiazin-6-yl)-5-methyl-2,4-pyrimidinediamine;
II-41: N2-(4-Aminosulfonylphenyl)-N4-(4-butyl-3-oxo-2H-benzo[1,4]thiazin-6-yl)-5-chloro-2,4-pyrimidinediamine;
II-42: N2-[3-(N-Ethylaminosulfonyl)-4-methylphenyl]-5-chloro-N4-(4-methyl-3-oxo-2H-benzo[1,4]thiazin-6-yl)-2,4-pyrimidinediamine;
II-43: N2-(3-Aminosulfonylphenyl)-N4-[2,2-dimethyl-3-oxo-4-(2-propynyl)-5-pyrido[1,4]oxazin-6-yl]-5-fluoro-2,4-pyrimidinediamine;
II-44: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-[2,2-dimethyl-3-oxo-4-(2-propynyl)-5-pyrido[1,4]oxazin-6-yl]-5-fluoro-2,4-pyrimidinediamine;
II-45: N2-(3-Aminosulfonyl-4-methylphenyl)-5-fluoro-N4-(3-oxo-2,2,4-trimethyl-5-pyrido[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-46: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-[2,2-dimethyl-3-oxo-4-(2-(N-morpholinyl)ethyl)-5-pyrido[1,4]oxazin-6-yl]-5-fluoro-2,4-pyrimidinediamine;
II-47: N2-(4-Aminosulfonylphenyl)-N4-[2,2-dimethyl-3-oxo-4-(2-(N-morpholinyl)ethyl)-5-pyrido[1,4]oxazin-6-yl]-5-fluoro-2,4-pyrimidinediamine;
II-48: N2-(3-N,N-Dimethylaminosulfonylphenyl)-5-fluoro-N4-[3-oxo-2,2,4-trimethyl-5-pyrido[1,4]oxazin-6-yl]-2,4-pyrimidinediamine;
II-49: N2-(3-N,N-Dimethylaminosulfonylphenyl)-N4-[2,2-dimethyl-3-oxo-4-(2-propynyl)-5-pyrido[1,4]oxazin-6-yl]-5-fluoro-2,4-pyrimidinediamine;
II-50: N2-(3-N,N-Dimethylaminosulfonylphenyl)-N4-[2,2-dimethyl-3-oxo-4H-5-pyrido[1,4]oxazin-6-yl]-5-fluoro-2,4-pyrimidinediamine;
II-51: N2-(3-Aminosulfonylphenyl)-5-chloro-N4-[2,2-dimethyl-3-oxo-4H-5-pyrido[1,4]oxazin-6-yl]-2,4-pyrimidinediamine;
II-52: N2-(3-Aminosulfonyl-4-methylphenyl)-5-chloro-N4-[2,2-dimethyl-3-oxo-4H-5-pyrido[1,4]oxazin-6-yl]-2,4-pyrimidinediamine;
II-53: N2-(4-Aminosulfonylphenyl)-5-chloro-N4-[2,2-dimethyl-3-oxo-4H-5-pyrido[1,4]oxazin-6-yl]-2,4-pyrimidinediamine;
II-54: N2-(3-Aminosulfonylphenyl)-N4-(2,2-dimethyl-3-oxo-4H-benzo[1,4]oxazin-6-yl)-5-methyl-2,4-pyrimidinediamine;
II-55: N2-(4-Aminosulfonylphenyl)-N4-(2,2-dimethyl-3-oxo-4H-benzo[1,4]oxazin-6-yl)-5-methyl-2,4-pyrimidinediamine;
II-56: N2-(3-Aminosulfonylphenyl)-N4-(3-oxo-2,2,4-trimethylbenzo[1,4]oxazin-6-yl)-5-methyl-2,4-pyrimidinediamine;
II-57: N2-(4-Aminosulfonylphenyl)-N4-(3-oxo-2,2,4-trimethylbenzo[1,4]oxazin-6-yl)-5-methyl-2,4-pyrimidinediamine;
II-58: N2-(3-Aminosulfonylphenyl)-5-fluoro-N4-(3-oxo-2,2,4-trimethyl-5-pyrido[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-59: N2-(4-Aminosulfonylphenyl)-5-fluoro-N4-(3-oxo-2,2,4-trimethyl-5-pyrido[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-60: N2-(3-Aminosulfonylphenyl)-N4-(2,2-dimethyl-3-oxo-4-(2-propynyl)-benzo[1,4]oxazin-6-yl)-5-methyl-2,4-pyrimidinediamine;
II-61: N2-(4-Aminosulfonylphenyl)-N4-(2,2-dimethyl-4-(2-propynyl)-3-oxo-benzo[1,4]oxazin-6-yl)-5-methyl-2,4-pyrimidinediamine;
II-62: N2-(3-Aminosulfonylphenyl)-N4-(3-oxo-2,2,4-trimethyl-5-pyrido[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-63: N2-(4-Aminosulfonylphenyl)-N4-(3-oxo-2,2,4-trimethyl-5-pyrido[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-64: N2-(3-Aminosulfonylphenyl)-5-methyl-N4-(3-oxo-2,2,4-trimethylbenzo[1,4]thiazin-6-yl)-2,4-pyrimidinediamine;
II-65: N2-(4-Aminosulfonylphenyl)-5-methyl-N4-(2,2,4-trimethyl-3-oxobenzo[1,4]thiazin-6-yl)-2,4-pyrimidinediamine;
II-66: N2-(3-Aminosulfonylphenyl)-N4-(4-cyclopropylmethyl-2,2-dimethyl-3-oxo-5-pyrido[1,4]oxazin-6-yl)-5-fluoro-2,4-pyrimidinediamine;
II-67: N2-(4-Aminosulfonylphenyl)-N4-(4-cyclopropylmethyl-2,2-dimethyl-3-oxo-5-pyrido[1,4]oxazin-6-yl)-5-fluoro-2,4-pyrimidinediamine;
II-68: N2-(3-Aminosulfonylphenyl)-N4-[2,2-dimethyl-3-oxo-4-(2-propynyl)benzo[1,4]thiazin-6-yl]-5-methyl-2,4-pyrimidinediamine;
II-69: N2-(4-Aminosulfonylphenyl)-N4-[2,2-dimethyl-3-oxo-4-(2-propynyl)benzo[1,4]thiazin-6-yl]-5-methyl-2,4-pyrimidinediamine;
II-70: N2-(3-Aminosulfonylphenyl)-N4-(2,2-dimethyl-3-oxo-4H-5-pyrido[1,4]oxazin-6-yl)-5-methyl-2,4-pyrimidinediamine;
II-71: N2-(4-Aminosulfonylphenyl)-N4-(2,2-dimethyl-3-oxo-4H-5-pyrido[1,4]oxazin-6-yl)-5-methyl-2,4-pyrimidinediamine;
II-72: 5-Methyl-N2-[4-methyl-3-(N-methylaminosulfonyl)phenyl]-N4-(3-oxo-2,2,4-trimethylbenzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-73: 5-Methyl-N2-[4-methyl-3-(N-methylaminosulfonyl)phenyl]-N4-(4-methyl-3-oxo-2H-benzo[1,4]thiazin-6-yl)-2,4-pyrimidinediamine;
II-74: N2-(3-Aminosulfonylphenyl)-N4-(3-oxo-2,2,4-trimethyl-5-pyrido[1,4]oxazin-6-yl)-5-[2-(trimethylsilyl)ethynyl]-2,4-pyrimidinediamine;
II-75: N2-(3-Aminosulfonylphenyl)-5-ethynyl-N4-(3-oxo-2,2,4-trimethyl-5-pyrido[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-76: N2-(3-Aminosulfonylphenyl)-5-methyl-N4-(3-oxo-2,2,4-trimethyl-5-pyrido[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-77: N2-(4-Aminosulfonylphenyl)-5-methyl-N4-(3-oxo-2,2,4-trimethyl-5-pyrido[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-78: N2-[3-(N-Ethylaminosulfonyl)-4-methylphenyl]-5-methyl-N4-(3-oxo-2,2,4-trimethyl-5-pyrido[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-79: N2-(4-Aminosulfonylphenyl)-5-cyclopropyl-N4-(4-methyl-3-oxo-2H-benzo[1,4]thiazin-6-yl)-2,4-pyrimidinediamine;
II-80: N2-(3-Aminosulfonylphenyl)-5-cyclopropyl-N4-(4-methyl-3-oxo-2H-benzo[1,4]thiazin-6-yl)-2,4-pyrimidinediamine;
II-81: N4-(2,2-Dimethyl-3-oxo-4H-5-pyrido[1,4]oxazin-6-yl)-N2-[3-(N-ethylaminosulfonyl)-4-methylphenyl]-5-methyl-2,4-pyrimidinediamine;
II-82: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-(2,2-dimethyl-3-oxo-4H-5-pyrido[1,4]oxazin-6-yl)-5-methyl-2,4-pyrimidinediamine;
II-83: N2-(3-Aminosulfonyl-4-methylphenyl)-5-methyl-N4-(3-oxo-2,2,4-trimethylbenzo[1,4]thiazin-6-yl)-2,4-pyrimidinediamine;
II-84: N2-(3-Aminosulfonyl-4-methylphenyl)-5-methyl-N4-(3-oxo-2,2,4-trimethyl-5-pyrido[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-85: N2-(3-Aminosulfonylphenyl)-5-methyl-N4-[3-oxo-4-propyl-2H-5-pyrido[1,4]oxazin-6-yl]-2,4-pyrimidinediamine;
II-86: N2-(4-Aminosulfonylphenyl)-5-methyl-N4-[3-oxo-4-propyl-2H-5-pyrido[1,4]oxazin-6-yl]-2,4-pyrimidinediamine;
II-87: N2-(3-Aminosulfonyl-4-methylphenyl)-5-methyl-N4-[3-oxo-4-propyl-2H-5-pyrido[1,4]oxazin-6-yl]-2,4-pyrimidinediamine;
II-88: N2-[3-(N-Ethylaminosulfonyl)-4-methylphenyl]-5-methyl-N4-[3-oxo-4-propyl-2H-5-pyrido[1,4]oxazin-6-yl]-2,4-pyrimidinediamine;
II-89: N2-(3-Aminosulfonylphenyl)-5-methyl-N4-(4-methyl-3-oxo-2H-5-pyrido[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-90: N2-[4-Aminosulfonylphenyl])-5-methyl-N4-(4-methyl-3-oxo-2H-5-pyrido[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-91: N2-(3-Aminosulfonyl-4-methylphenyl)-5-methyl-N4-(4-methyl-3-oxo-2H-5-pyrido[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-92: N2-[3-(N-Ethylaminosulfonyl)-4-methylphenyl]-5-methyl-N4-(4-methyl-3-oxo-2H-5-pyrido[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-93: N2-[3-(N-Cyclopropylaminosulfonyl)phenyl]-5-methyl-N4-(3-oxo-2,2,4-trimethyl-5-pyrido[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-94: N2-[4-(N-Cyclopropylaminosulfonyl)phenyl]-5-methyl-N4-(4-methyl-3-oxo-2H-5-pyrido[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-95: N2-[3-(N-Cyclopropylaminosulfonyl)-4-methylphenyl]-5-methyl-N4-(3-oxo-2,2,4-trimethyl-5-pyrido[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-96: 5-Methyl-N2-[4-methyl-3-(N-methylaminosulfonyl)phenyl]-N4-(3-oxo-2,2,4-trimethyl-5-pyrido[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-97: N2-(3-Aminosulfonylphenyl)-5-methyl-N4-(3-oxo-2H,4H-5-pyrido[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-98: N2-(4-Aminosulfonylphenyl)-5-methyl-N4-(3-oxo-2H,4H-5-pyrido[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-99: N2-(3-Aminosulfonyl-4-methylphenyl)-5-methyl-N4-(3-oxo-2H,4H-5-pyrido[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-100: 5-Methyl-N2-[4-methyl-3-(N-methylaminosulfonyl)phenyl]-N4-(3-oxo-2H,4H-5-pyrido[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-101: N2-[3-(N-Ethylaminosulfonyl)-4-methylphenyl]-5-methyl-N4-(3-oxo-2H,4H-5-pyrido[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-102: 5-Methyl-N4-(3-oxo-2H,4H-benzo[1,4]oxazin-6-yl)-N2-[3-(N-propionylaminosulfonyl)phenyl[-2,4-pyrimidinediamine;
II-103: 5-Methyl-N4-[3-oxo-4-propionyl-2H-benzo[1,4]oxazin-6-yl]-N2-[3-(N-propionylaminosulfonyl)phenyl]-2,4-pyrimidinediamine;
II-104: 5-Methyl-N4-(3-oxo-2,2,4-trimethylbenzo[1,4]oxazin-6-yl)-N2-[4-(N-propionylaminosulfonyl)phenyl]-2,4-pyrimidinediamine;
II-105: 5-Methyl-N4-(3-oxo-2H,4H-benzo[1,4]oxazin-6-yl)-N2-[3-(N-propionylaminosulfonyl)phenyl]-2,4-pyrimidinediamine Sodium Salt;
II-106: 5-Methyl-N4-(3-oxo-2,2,4-trimethylbenzo[1,4]oxazin-6-yl)-N2-[4-(N-propionylaminosulfonyl)phenyl]-2,4-pyrimidinediamine Sodium Salt;
II-107: N2-(3-Aminosulfonylphenyl)-5-chloro-N4-(3-oxo-4-propyl-2H-benzo[1,4]thiazin-6-yl)-2,4-pyrimidinediamine;
II-108: N2-(3-Aminosulfonyl-4-methylphenyl)-5-chloro-N4-(3-oxo-4-propyl-2H-benzo[1,4]thiazin-6-yl)-2,4-pyrimidinediamine;
II-109: N2-[3-(N-Ethylaminosulfonyl)-4-methylphenyl]-5-chloro-N4-(3-oxo-4-propyl-2H-benzo[1,4]thiazin-6-yl)-2,4-pyrimidinediamine;
II-110: N2-(4-Aminosulfonylphenyl)-5-methyl-N4-(3-oxo-4-propyl-2H-benzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-111: N2-(4-Aminosulfonylphenyl)-5-fluoro-N4-(3-oxo-4-propyl-2H-benzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-112: N2-(4-Aminosulfonylphenyl)-5-chloro-N4-(3-oxo-4-propyl-2H-benzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-113: N2-(3-Aminosulfonyl-4-methylphenyl)-5-chloro-N4-(3-oxo-4-propyl-2H-benzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-114: 5-Methyl-N2-[4-methyl-3-(N-methylaminosulfonyl)phenyl]-N4-(3-oxo-2H,4H-benzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-115: 5-Methyl-N2-[4-methyl-3-(N-methylaminosulfonyl)phenyl]-N4-(3-oxo-2H,4H-benzo[1,4]thiazin-6-yl)-2,4-pyrimidinediamine;
II-116: N2-(3-Aminosulfonylphenyl)-5-chloro-N4-(4-methyl-3-oxo-2H-benzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-117: N2-(3-Aminosulfonyl-4-methylphenyl)-5-chloro-N4-(4-methyl-3-oxo-2H-benzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-118: 5-Chloro-N2-[4-methyl-3-(N-methylaminosulfonyl)phenyl]-N4-(4-methyl-3-oxo-2H-benzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-119: 5-Chloro-N2-[3-(N-ethylaminosulfonyl)-4-methylphenyl]-N4-(4-methyl-3-oxo-2H-benzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-120: N2-(3-Aminosulfonylphenyl)-5-methyl-N4-(3-oxo-4-propyl-2H-benzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-121: N2-(3-Aminosulfonyl-4-methylphenyl)-5-methyl-N4-(3-oxo-4-propyl-2H-benzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-122: 5-Methyl-N2-[4-methyl-3-(N-methylaminosulfonyl)phenyl]-N4-(3-oxo-4-propyl-2H-benzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-123: N2-(3-Aminosulfonylphenyl)-5-fluoro-N4-(3-oxo-4-propyl-2H-benzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-124: N2-(3-Aminosulfonyl-4-methylphenyl)-5-fluoro-N4-(3-oxo-4-propyl-2H-benzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-125: 5-Fluoro-N2-[4-methyl-3-(N-methylaminosulfonyl)phenyl]-N4-(3-oxo-4-propyl-2H-benzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-126: N2-[3-(N-Ethylaminosulfonyl)-4-methylphenyl]-5-fluoro-N4-(3-oxo-4-propyl-2H-benzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-127: 5-Chloro-N2-[4-methyl-3-(N-methylaminosulfonyl)phenyl]-N4-(3-oxo-4-propyl-2H-benzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-128: 5-Chloro-N2-[3-(N-ethylaminosulfonyl)-4-methylphenyl]-N4-(3-oxo-4-propyl-2H-benzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-129: N4-(4-Ethyl-3-oxo-2H-benzo[1,4]oxazin-6-yl)-5-methyl-N2-[4-methyl-3-(N-methylaminosulfonyl)phenyl]-2,4-pyrimidinediamine;
II-130: N2-(3-Aminosulfonylphenyl)-5-chloro-N4-(4-ethyl-3-oxo-2H-benzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-131: N2-(3-Aminosulfonyl-4-methylphenyl)-5-chloro-N4-(4-ethyl-3-oxo-2H-benzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-132: N2-[3-(N-Ethylaminosulfonyl)-4-methylphenyl]-5-methyl-N4-(3-oxo-4-propyl-2H-benzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-133: N2-(3-Aminosulfonylphenyl)-5-chloro-N4-(3-oxo-4-propyl-2H-benzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-134: 5-Methyl-N2-[4-methyl-3-(N-methylaminosulfonyl)phenyl]-N4-(3-oxo-4-propyl-2H-benzo[1,4]thiazin-6-yl)-2,4-pyrimidinediamine;
II-135: 5-Chloro-N2-[4-methyl-3-(N-methylaminosulfonyl)phenyl]-N4-(4-methyl-3-oxo-2H-benzo[1,4]thiazin-6-yl)-2,4-pyrimidinediamine;
II-136: 5-Chloro-N2-[4-methyl-3-(N-methylaminosulfonyl)phenyl]-N4-(3-oxo-4-propyl-2H-benzo[1,4]thiazin-6-yl)-2,4-pyrimidinediamine;
II-137: 5-Chloro-N4-(4-ethyl-3-oxo-2H-benzo[1,4]oxazin-6-yl)-N2-[4-methyl-3-(N-methylaminosulfonyl)phenyl]-2,4-pyrimidinediamine;
II-138: 5-Chloro-N4-(4-ethyl-3-oxo-2H-benzo[1,4]oxazin-6-yl)-N2-[3-(N-ethylaminosulfonyl)-4-methylphenyl]-2,4-pyrimidinediamine;
II-139: 5-Chloro-N4-(4-methyl-3-oxo-2H-benzo[1,4]oxazin-6-yl)-N2-[3-(N-methylaminosulfonyl)phenyl]-2,4-pyrimidinediamine;
II-140: 5-Chloro-N4-(4-ethyl-3-oxo-2H-benzo[1,4]oxazin-6-yl)-N2-[3-(N-methylaminosulfonyl)phenyl]-2,4-pyrimidinediamine;
II-141: 5-Chloro-N2-[3-(N-methylaminosulfonyl)phenyl]-N4-(3-oxo-4-propyl-2H-benzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
II-142: 5-Chloro-N4-(4-methyl-3-oxo-2H-benzo[1,4]thiazin-6-yl)-N2-[3-(N-methylaminosulfonyl)phenyl]-2,4-pyrimidinediamine;
II-143: 5-Chloro-N2-[3-(N-methylaminosulfonyl)phenyl]-N4-(3-oxo-4-propyl-2H-benzo[1,4]thiazin-6-yl)-2,4-pyrimidinediamine;
II-144: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-[4-(2-fluoroethyl)-3-oxo-2H-benzo[1,4]oxazin-6-yl]-5-methyl-2,4-pyrimidinediamine;
II-145: N2-(4-Aminosulfonylphenyl)-N4-[4-(2-fluoroethyl)-3-oxo-2H-benzo[1,4]oxazin-6-yl]-5-methyl-2,4-pyrimidinediamine;
II-146: N2-(3-Aminosulfonylphenyl)-N4-[4-(2-fluoroethyl)-3-oxo-2H-benzo[1,4]oxazin-6-yl]-5-methyl-2,4-pyrimidinediamine;
II-147: N2-(4-Aminosulfonylphenyl)-5-chloro-N4-[4-(2-fluoroethyl)-3-oxo-2H-benzo[1,4]oxazin-6-yl]-2,4-pyrimidinediamine;
II-148: N2-(3-Aminosulfonyl-4-methylphenyl)-5-chloro-N4-[4-(2-fluoroethyl)-3-oxo-2H-benzo[1,4]oxazin-6-yl]-2,4-pyrimidinediamine;
II-149: N2-(3-Aminosulfonylphenyl)-N4-(2,2-difluoro-4-methyl-3-oxobenzo[1,4]oxazin-6-yl)-5-methyl-2,4-pyrimidinediamine;
II-150: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-(2,2-difluoro-4-methyl-3-oxobenzo[1,4]oxazin-6-yl)-5-methyl-2,4-pyrimidinediamine;
II-151: N2-(4-Aminosulfonylphenyl)-N4-(2,2-difluoro-4-methyl-3-oxobenzo[1,4]oxazin-6-yl)-5-methyl-2,4-pyrimidinediamine;
II-152: N2-(4-Aminosulfonylphenyl)-N4-(2,2-difluoro-3-oxo-4H-benzo[1,4]oxazin-6-yl)-5-methyl-2,4-pyrimidinediamine;
II-153: N2-(3-Aminosulfonylphenyl)-N4-(2,2-difluoro-3-oxo-4H-benzo[1,4]oxazin-6-yl)-5-methyl-2,4-pyrimidinediamine;
II-154: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-(2,2-difluoro-3-oxo-4H-benzo[1,4]oxazin-6-yl)-5-methyl-2,4-pyrimidinediamine;
II-155: N2-(3-Aminosulfonylphenyl)-N4-[2,2-difluoro-3-oxo-4-(2-pyridinylmethyl)benzo[1,4]oxazin-6-yl]-5-methyl-2,4-pyrimidinediamine;
II-156: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-[2,2-difluoro-3-oxo-4-(2-pyridinylmethyl)benzo[1,4]oxazin-6-yl]-5-methyl-2,4-pyrimidinediamine;
II-157: N2-(4-Aminosulfonylphenyl)-N4-[2,2-difluoro-3-oxo-4-(2-pyridinylmethyl)benzo[1,4]oxazin-6-yl]-5-methyl-2,4-pyrimidinediamine;
II-158: N2-(4-(N-propionylsulfamoyl)phenyl)-N4-(2,2-dimethyl-4-methyl-3-oxobenzo[1,4]oxazin-6-yl)-5-methyl-2,4-pyrimidinediamine choline salt;
II-159: N2-(4-(N-propionylsulfamoyl)phenyl)-N4-(4-propyl-3-oxobenzo[1,4]oxazin-6-yl)-5-chloro-2,4-pyrimidinediamine sodium salt;
II-160: N2-(4-Aminosulfonylphenyl)-N4-(2,2-dimethyl-4-propyl-3-oxobenzo[1,4]oxazin-6-yl)-5-chloro-2,4-pyrimidinediamine;
II-161: N2-(4-Aminosulfonylphenyl)-5-chloro-N4-[3-oxo-4-(2-propynyl)-2H-benzo[1,4]thiazin-6-yl]-2,4-pyrimidinediamine;
II-162: N2-(4-Aminosulfonylphenyl)-N4-(4-ethyl-3-oxobenzo[1,4]oxazin-6-yl)-5-chloro-2,4-pyrimidinediamine;
III-1: N2-(3-Aminosulfonylphenyl)-N4-[2,2-dimethyl-3-oxo-4H-5-pyrido[1,4]oxazin-7-yl]-5-methyl-2,4-pyrimidinediamine;
III-2: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-[2,2-dimethyl-3-oxo-4H-5-pyrido[1,4]oxazin-7-yl]-5-methyl-2,4-pyrimidinediamine;
III-3: N2-(4-Aminosulfonylphenyl)-N4-[2,2-dimethyl-3-oxo-4H-5-pyrido[1,4]oxazin-7-yl]-5-methyl-2,4-pyrimidinediamine;
III-4: N2-(4-Aminosulfonylphenyl)-N4-(2,2-difluoro-3-oxo-4H-5-pyrido[1,4]oxazin-7-yl)-5-methyl-2,4-pyrimidinediamine;
III-5: N2-(3-Aminosulfonylphenyl)-N4-(2,2-difluoro-3-oxo-4H-5-pyrido[1,4]oxazin-7-yl)-5-methyl-2,4-pyrimidinediamine;
III-6: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-(2,2-difluoro-3-oxo-4H-5-pyrido[1,4]oxazin-7-yl)-5-methyl-2,4-pyrimidinediamine;
III-7: N2-(3-Aminosulfonylphenyl)-5-fluoro-N4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-8: N2-(3-Aminosulfonyl-4-methylphenyl)-5-methyl-N4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-9: N2-(3-Aminosulfonylphenyl)-5-methyl-N4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-10: N2-(4-Aminosulfonylphenyl)-5-methyl-N4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-11: N2-(3-Aminosulfonyl-4-methylphenyl)-5-methyl-N4-(2-oxo-1-(2-propynyl)-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-12: N2-(3-Aminosulfonylphenyl)-5-methyl-N4-(2-oxo-1-(2-propynyl)-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-13: N2-(3-Aminosulfonyl-4-methylphenyl)-5-methyl-N4-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-14: N2-(3-Aminosulfonylphenyl)-5-methyl-N4-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-15: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-(1-ethyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-5-methyl-2,4-pyrimidinediamine;
III-16: N2-(3-Aminosulfonylphenyl)-N4-(1-ethyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-5-methyl-2,4-pyrimidinediamine;
III-17: N2-(4-Aminosulfonylphenyl)-5-methyl-N4-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-18: N2-[3-(N-Ethylaminosulfonyl)-4-methylphenyl]-5-methyl-N4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-19: 5-Methyl-N2-[3-(N-methylaminosulfonyl)-4-methylphenyl]-N4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-20: N2-[3-(N-Cyclopropylaminosulfonyl)-4-methylphenyl]-5-methyl-N4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine
III-21: 5-Methyl-N2-[3-(N-methylaminosulfonyl)-4-methylphenyl]-N4-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-22: N2-[3-(N-Ethylaminosulfonyl)-4-methylphenyl]-5-methyl-N4-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-23: 5-Methyl-N2-[3-(N-(1-methylethyl)aminosulfonyl)-4-methylphenyl]-N4-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-24: N2-[3-(N-Cyclopropylaminosulfonyl)-4-methylphenyl]-5-methyl-N4-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-25: N2-(3-Aminosulfonyl-4-methylphenyl)-5-methyl-N4-[1-(1-methylethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl]-2,4-pyrimidinediamine;
III-26: N2-[3-(N-Benzylaminosulfonyl)-4-methylphenyl]-5-methyl-N4-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-27: 5-Methyl-N2-[3-(N-(1-methylethyl)aminosulfonyl)phenyl]-N4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-28: 5-Methyl-N2-[3-(N-methylaminosulfonyl)phenyl]-N4-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-29: N2-[3-(N-Ethylaminosulfonyl)phenyl]-5-methyl-N4-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-30: N2-[3-(N-Cyclopropylaminosulfonyl)phenyl]-5-methyl-N4-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-31: 5-Methyl-N2-[3-(N-(1-methylethyl)aminosulfonyl)phenyl]-N4-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-32: N2-(3-Aminosulfonyl-4-methylphenyl)-5-chloro-N4-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-33: 5-Chloro-N2-[3-(N-methylaminosulfonyl)-4-methylphenyl]-N4-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-34: 5-Chloro-N2-[3-(N-ethylaminosulfonyl)-4-methylphenyl]-N4-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-35: 5-Chloro-N2-[3-(N-cyclopropylaminosulfonyl)-4-methylphenyl]-N4-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-36: 5-Chloro-N2-[3-(N-(1-methylethyl)aminosulfonyl)-4-methylphenyl]-N4-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-37: N2-(3-Aminosulfonylphenyl)-5-chloro-N4-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-38: 5-Chloro-N2-[3-(N-methylaminosulfonyl)phenyl]-N4-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-39: 5-Chloro-N2-[3-(N-ethylaminosulfonyl)phenyl]-N4-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-40: 5-Chloro-N2-[3-(N-cyclopropylaminosulfonyl)phenyl]-N4-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-41: 5-Chloro-N2-[3-(N-(1-methylethyl)aminosulfonyl)phenyl]-N4-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-42: N2-(3-Aminosulfonyl-4-methylphenyl)-5-chloro-N4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-43: 5-Chloro-N2-[3-(N-methylaminosulfonyl)-4-methylphenyl]-N4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-44: 5-Chloro-N2-[3-(N-ethylaminosulfonyl)-4-methylphenyl]-N4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-45: 5-Chloro-N2-[3-(N-cyclopropylaminosulfonyl)-4-methylphenyl]-N4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-46: N2-(3-Aminosulfonylphenyl)-5-chloro-N4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-47: 5-Chloro-N2-[3-(N-methylaminosulfonyl)phenyl]-N4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-48: 5-Chloro-N2-[3-(N-ethylaminosulfonyl)phenyl]-N4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-49: 5-Chloro-N2-[3-(N-cyclopropylaminosulfonyl)phenyl]-N4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-50: N2-[3-(N-Ethyl-N-propionylaminosulfonyl)-4-methylphenyl]-5-methyl-N4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
III-51: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-(3,3-dimethyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-5-methyl-2,4-pyrimidinediamine;
III-52: N2-[3-(N-Ethylaminosulfonyl)-4-methylphenyl]-N4-(3,3-dimethyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-5-methyl-2,4-pyrimidinediamine;
III-53: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-5-trifluoromethyl-2,4-pyrimidinediamine;
III-54: N2-[3-(N-methylaminosulfonyl)-4-methylphenyl]-N4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-5-trifluoromethyl-2,4-pyrimidinediamine;
III-55: N2-[3-(N-Ethylaminosulfonyl)-4-methylphenyl]-N4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-5-trifluoromethyl-2,4-pyrimidinediamine;
III-56: N2-(3-Aminosulfonylphenyl)-N4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-5-trifluoromethyl-2,4-pyrimidinediamine;
III-57: N2-[3-(N-Methylaminosulfonyl)phenyl]-N4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-5-trifluoromethyl-2,4-pyrimidinediamine;
III-58: N2-[3-(N-Ethylaminosulfonyl)phenyl]-N4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-5-trifluoromethyl-2,4-pyrimidinediamine;
III-59: N2-[3-(N-Diethoxyphosphinyl-N-ethylaminosulfonyl)-4-methylphenyl)-5-methyl-N4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,4-pyrimidinediamine;
IV-1: N2-(3-Aminosulfonylphenyl)-5-fluoro-N4-[2-(2-(N-morpholinyl)ethylaminocarbonyl)benzofuran-5-yl]-2,4-pyrimidinediamine;
IV-2: N2-(3-Aminosulfonyl-4-methylphenyl)-5-fluoro-N4-[2-(2-(N-morpholinyl)ethylaminocarbonyl)benzofuran-5-yl]-2,4-pyrimidinediamine;
IV-3: N2-(4-Aminosulfonylphenyl)-5-fluoro-N4-[2-(2-(N-morpholinyl)ethylaminocarbonyl)benzofuran-5-yl]-2,4-pyrimidinediamine;
IV-4: N2-(3-Aminosulfonylphenyl)-5-fluoro-N4-(1H-indol-5-yl)-2,4-pyrimidinediamine;
IV-5: N2-(3-Aminosulfonyl-4-methylphenyl)-5-fluoro-N4-(1H-indol-5-yl)-2,4-pyrimidinediamine;
IV-6: N2-(3-Aminosulfonylphenyl)-5-chloro-N4-(1H-indol-5-yl)-2,4-pyrimidinediamine;
IV-7: N2-(3-Aminosulfonyl-4-methylphenyl)-5-chloro-N4-(1H-indol-5-yl)-2,4-pyrimidinediamine;
IV-8: N2-(3-Aminosulfonyl-4-methylphenyl)-5-chloro-N4-[1-(cyclopropylaminocarbonyl)-1H-indol-5-yl]-2,4-pyrimidinediamine;
IV-9: N2-(4-Aminosulfonylphenyl)-5-chloro-N4-[1-(cyclopropylaminocarbonyl)-1H-indol-5-yl]-2,4-pyrimidinediamine;
IV-10: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-[1-(cyclopropylaminocarbonyl)-1H-indol-5-yl]-5-fluoro-2,4-pyrimidinediamine;
IV-11: N2-(3-Aminosulfonylphenyl)-N4-[1-(cyclopropylaminocarbonyl)-1H-indol-5-yl]-5-fluoro-2,4-pyrimidinediamine;
IV-12: N2-(3-Aminosulfonyl-4-methylphenyl)-5-fluoro-N4-[1-(methylaminocarbonyl)-1H-indol-5-yl]-2,4-pyrimidinediamine;
IV-13: N2-(3-Aminosulfonylphenyl)-5-fluoro-N4-[1-(methylaminocarbonyl)-1H-indol-5-yl]-2,4-pyrimidinediamine;
IV-14: N2-(4-Aminosulfonylphenyl)-5-fluoro-N4-[1-(methylaminocarbonyl)-1H-indol-5-yl]-2,4-pyrimidinediamine;
IV-15: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-[1-(cyclopropylaminocarbonyl)-1H-indol-5-yl]-5-methyl-2,4-pyrimidinediamine;
IV-16: N2-(3-Aminosulfonylphenyl)-N4-[1-(cyclopropylaminocarbonyl)-1H-indol-5-yl]-5-methyl-2,4-pyrimidinediamine;
IV-17: N2-(4-Aminosulfonylphenyl)-N4-[1-(cyclopropylaminocarbonyl)-1H-indol-5-yl]-5-methyl-2,4-pyrimidinediamine;
IV-18: N2-(3-Aminosulfonyl-4-methylphenyl)-5-methyl-N4-[1-(methylaminocarbonyl)-1H-indol-5-yl]-2,4-pyrimidinediamine;
IV-19: N2-(3-Aminosulfonylphenyl)-5-methyl-N4-[1-(methylaminocarbonyl)-1H-indol-5-yl]-2,4-pyrimidinediamine;
IV-20: N2-(4-Aminosulfonylphenyl)-5-methyl-N4-[1-(methylaminocarbonyl)-1H-indol-5-yl]-2,4-pyrimidinediamine;
IV-21: N2-(4-Aminosulfonylphenyl)-N4-[1-(cyclopropylaminocarbonyl)-1H-indol-5-yl]-5-fluoro-2,4-pyrimidinediamine;
IV-22: N2-(3-Aminosulfonyl-4-methylphenyl)-5-methyl-N4-[1-(4-pyridinyl)-1H-indol-5-yl]-2,4-pyrimidinediamine;
IV-23: N2-[3-(N-Cyclopropylaminosulfonyl)phenyl]-5-methyl-N4-[1-(4-pyridinyl)-1H-indol-5-yl]-2,4-pyrimidinediamine;
IV-24: N2-[4-(N-Cyclopropylaminosulfonyl)phenyl]-5-methyl-N4-[1-(4-pyridinyl)-1H-indol-5-yl]-2,4-pyrimidinediamine;
IV-25: N2-(4-Aminosulfonylphenyl)-5-methyl-N4-[1-(4-pyridinyl)-1H-indol-5-yl]-2,4-pyrimidinediamine;
IV-26: N2-(3-Aminosulfonylphenyl)-5-methyl-N4-[1-(4-pyridinyl)-1H-indol-5-yl]-2,4-pyrimidinediamine;
V-1: N2-(3-Aminosulfonyl-4-methylphenyl)-5-fluoro-N4-[1-(2-(N-morpholinyl)ethyl)-1H-indol-6-yl]-2,4-pyrimidinediamine;
V-2: N2-(3-Aminosulfonylphenyl)-5-fluoro-N4-[1-(2-(N-morpholinyl)ethyl)-1H-indol-6-yl]-2,4-pyrimidinediamine;
V-3: N2-(3-Aminosulfonyl-4-methylphenyl)-5-fluoro-N4-[1-(2-(N-morpholinyl)ethylaminocarbonyl)-1H-indol-6-yl]-2,4-pyrimidinediamine;
V-4: N2-(3-Aminosulfonylphenyl)-5-fluoro-N4-[1-(2-(N-morpholinyl)ethylaminocarbonyl)-1H-indol-6-yl]-2,4-pyrimidinediamine;
V-5: N2-(4-Aminosulfonylphenyl)-5-fluoro-N4-[1-(2-(N-morpholinyl)ethylaminocarbonyl)-1H-indol-6-yl]-2,4-pyrimidinediamine;
VI-1: N2-(3-Aminosulfonylphenyl)-5-fluoro-N4-(1-oxo-1,2,3,4-tetrahydroisoquinolin-7-yl)-2,4-pyrimidinediamine;
VI-2: N2-(3-Aminosulfonyl-4-methylphenyl)-5-fluoro-N4-(1-oxo-1,2,3,4-tetrahydroisoquinolin-7-yl)-2,4-pyrimidinediamine;
VI-3: N2-(4-Aminosulfonylphenyl)-5-fluoro-N4-(1-oxo-1,2,3,4-tetrahydroisoquinolin-7-yl)-2,4-pyrimidinediamine;
VI-4: N2-(3-Aminosulfonyl-4-methylphenyl)-5-fluoro-N4-(8-oxo-5,6,7,8-tetrahydronapthalen-2-yl)-2,4-pyrimidinediamine;
VI-5: N2-(3-Aminosulfonylphenyl)-5-fluoro-N4-(8-oxo-5,6,7,8-tetrahydronapthalen-2-yl)-2,4-pyrimidinediamine;
VI-6: N2-(4-Aminosulfonylphenyl)-5-fluoro-N4-(8-oxo-5,6,7,8-tetrahydronapthalen-2-yl)-2,4-pyrimidinediamine;
VII-1: N2-(3-Aminosulfonyl-4-methylphenyl)-5-fluoro-N4-(5-oxo-5,6,7,8-tetrahydronapthalen-2-yl)-2,4-pyrimidinediamine;
VII-2: N2-(3-Aminosulfonylphenyl)-5-fluoro-N4-(5-oxo-5,6,7,8-tetrahydronapthalen-2-yl)-2,4-pyrimidinediamine;
VII-3: N2-(4-Aminosulfonylphenyl)-5-fluoro-N4-(5-oxo-5,6,7,8-tetrahydronapthalen-2-yl)-2,4-pyrimidinediamine;
VIII-1: N4-(6-Aminocarbonylnaphthalen-2-yl)-N2-(3-aminosulfonylphenyl)-5-chloro-2,4-pyrimidinediamine;
VIII-2: N4-(6-Aminocarbonylnaphthalen-2-yl)-N2-(3-aminosulfonyl-4-methylphenyl)-5-chloro-2,4-pyrimidinediamine;
VIII-3: N4-(6-Aminocarbonylnaphthalen-2-yl)-N2-(4-aminosulfonylphenyl)-5-chloro-2,4-pyrimidinediamine;
VIII-4: N2-(4-Aminosulfonylphenyl)-5-chloro-N4-(6-cyanonaphthalen-2-yl)-2,4-pyrimidinediamine;
VIII-5: N2-(3-Aminosulfonyl-4-methylphenyl)-5-chloro-N4-(6-cyanonaphthalen-2-yl)-2,4-pyrimidinediamine;
VIII-6: N2-(3-Aminosulfonyl-4-methylphenyl)-5-fluoro-N4-(6-methoxycarbonyl-naphthalen-2-yl)-2,4-pyrimidinediamine;
IX-1: N2-(3-Aminosulfonylphenyl)-5-fluoro-N4-(2-methylbenzoxazol-5-yl)-2,4-pyrimidinediamine;
IX-2: N2-(3-Aminosulfonylphenyl)-5-fluoro-N4-[1-(3-hydroxypropyl)-2-methyl-1H-benzimidazol-5-yl]-2,4-pyrimidinediamine;
IX-3: N2-(3-Aminosulfonylphenyl)-5-fluoro-N4-[1-(3-hydroxypropyl)-2-trifluoromethyl-1H-benzimidazol-5-yl]-2,4-pyrimidinediamine;
IX-4: N2-(3-Aminosulfonylphenyl)-5-fluoro-N4-[1-methyl-2-(4-morpholino)-1H-benzimidazol-5-yl]-2,4-pyrimidinediamine;
X-1: N2-(3-Aminosulfonylphenyl)-5-fluoro-N4-[2-(N-morpholinyl)-1H-benzimidazol-6-yl]-2,4-pyrimidinediamine;
XI-1: N2-(3-Aminosulfonylphenyl)-N4-(1-cyclopropylmethyl-1H-indazol-5-yl)-5-methyl-2,4-pyrimidinediamine;
XI-2: N2-(4-Aminosulfonylphenyl)-N4-(1-cyclopropylmethyl-1H-indazol-5-yl)-5-methyl-2,4-pyrimidinediamine;
XI-3: N2-(3-Aminosulfonylphenyl)-N4-[1-(3-methoxypropyl)-1H-indazol-5-yl]-5-methyl-2,4-pyrimidinediamine;
XI-4: N2-(4-Aminosulfonylphenyl)-N4-[1-(3-methoxypropyl)-1H-indazol-5-yl]-5-methyl-2,4-pyrimidinediamine;
XI-5: N2-(3-Aminosulfonylphenyl)-N4-[1-(2-methoxyethyl)-1H-indazol-5-yl]-5-methyl-2,4-pyrimidinediamine;
XI-6: N2-(3-Aminosulfonylphenyl)-5-methyl-N4-[1-(1-methylethyl)-1H-indazol-5-yl]-2,4-pyrimidinediamine;
XI-7: N2-(4-Aminosulfonylphenyl)-5-methyl-N4-[1-(1-methylethyl)-1H-indazol-5-yl)-2,4-pyrimidinediamine;
XI-8: N2-(3-Aminosulfonylphenyl)-5-methyl-N4-(1-methyl-1H-indazol-5-yl)-2,4-pyrimidinediamine;
XI-9: N2-(4-Aminosulfonylphenyl)-5-methyl-N4-(1-methyl-1H-indazol-5-yl)-2,4-pyrimidinediamine;
XI-10: N2-(3-Aminosulfonylphenyl)-N4-(1-ethyl-1H-indazol-5-yl)-5-methyl-2,4-pyrimidinediamine;
XI-12: N2-(3-Aminosulfonylphenyl)-N4-(1-cyclohexyl-1H-indazol-5-yl)-5-methyl-2,4-pyrimidinediamine;
XI-13: N2-(3-Aminosulfonylphenyl)-5-methyl-N4-[1-(2-propynyl)-1H-indazol-5-yl]-2,4-pyrimidinediamine;
XI-14: N2-(3-Aminosulfonyl-4-methylphenyl)-5-methyl-N4-[1-(2-propynyl)-1H-indazol-5-yl]-2,4-pyrimidinediamine;
XI-15: N2-[3-(N-Ethylaminosulfonyl)-4-methylphenyl]-5-methyl-N4-[1-(2-propynyl)-1H-indazol-5-yl]-2,4-pyrimidinediamine;
XI-16: N2-[3-(N-Cyclopropylaminosulfonyl)phenyl]-5-methyl-N4-[1-(2-propynyl)-1H-indazol-5-yl]-2,4-pyrimidinediamine;
XI-17: N2-[3-(N-Cyclopropylaminosulfonyl)-4-methylphenyl]-5-methyl-N4-[1-(2-propynyl)-1H-indazol-5-yl]-2,4-pyrimidinediamine;
XI-18: N2-(3-Aminosulfonylphenyl)-5-methyl-N4-[1-(3-methylthiopropyl)-1H-indazol-5-yl]-2,4-pyrimidinediamine;
XI-19: N2-(3-Aminosulfonyl-4-methylphenyl)-5-methyl-N4-[1-(3-methylthiopropyl)-1H-indazol-5-yl]-2,4-pyrimidinediamine;
XI-20: N2-[3-(N-Cyclopropylaminosulfonyl)phenyl]-5-methyl-N4-[1-(3-methylthiopropyl)-1H-indazol-5-yl]-2,4-pyrimidinediamine;
XI-21: N2-[3-(N-Ethylaminosulfonyl)-4-methylphenyl]-5-methyl-N4-[1-(3-methylthiopropyl)-1H-indazol-5-yl]-2,4-pyrimidinediamine;
XI-22: 5-Methyl-N2-[4-methyl-3-(N-methylaminosulfonyl)phenyl]-N4-[1-(3-methylthiopropyl)-1H-indazol-5-yl]-2,4-pyrimidinediamine;
XI-23: N2-(3-Aminosulfonylphenyl)-N4-(1-cyclohexylmethyl-1H-indazol-5-yl)-5-methyl-2,4-pyrimidinediamine;
XI-24: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-(1-cyclohexylmethyl-1H-indazol-5-yl)-5-methyl-2,4-pyrimidinediamine;
XI-25: N4-(1-Cyclohexylmethyl-1H-indazol-5-yl)-5-methyl-N2-[4-methyl-3-(N-methylaminosulfonyl)phenyl]-2,4-pyrimidinediamine;
XII-1: N2-(3-Aminosulfonylphenyl)-N4-[1-(2-methoxyethyl)-1H-indazol-6-yl]-5-methyl-2,4-pyrimidinediamine;
XII-2: N2-(4-Aminosulfonylphenyl)-N4-[1-(2-methylethyl)-1H-indazol-6-yl]-5-methyl-2,4-pyrimidinediamine;
XII-3: N2-(3-Aminosulfonylphenyl)-5-methyl-N4-[1-(1-methylethyl)-1H-indazol-6-yl]-2,4-pyrimidinediamine;
XII-4: N2-(4-Aminosulfonylphenyl)-5-methyl-N4-[1-(1-methylethyl)-1H-indazol-6-yl]-2,4-pyrimidinediamine;
XII-5: N2-(3-Aminosulfonylphenyl)-5-methyl-N4-(1-methyl-1H-indazol-6-yl)-2,4-pyrimidinediamine;
XII-6: N2-(4-Aminosulfonylphenyl)-5-methyl-N4-(1-methyl-1H-indazol-6-yl)-2,4-pyrimidinediamine;
XII-7: N2-(3-Aminosulfonylphenyl)-N4-(1-ethyl-1H-indazol-6-yl)-5-methyl-2,4-pyrimidinediamine;
XII-8: N2-(4-Aminosulfonylphenyl)-N4-(1-ethyl-1H-indazol-6-yl)-5-methyl-2,4-pyrimidinediamine;
XII-9: 5-Methyl-N4-(1-methyl-1H-indazol-6-yl)-N2-[4-methyl-3-(N-methylaminosulfonyl)phenyl]-2,4-pyrimidinediamine;
XII-10: N2-(3-Aminosulfonylphenyl)-N4-[1-cyclopropylmethyl-3-methyl-1H-indazol-6-yl]-5-methyl-2,4-pyrimidinediamine;
XII-11: N2-(3-Aminosulfonyl-4-methylphenyl)-N4-[1-cyclopropylmethyl-3-methyl-1H-indazol-6-yl]-5-methyl-2,4-pyrimidinediamine;
XII-12: N4-[1-Cyclopropylmethyl-3-methyl-1H-indazol-6-yl]-N2-[3-(N-ethylaminosulfonyl)-4-methylphenyl]-5-methyl-2,4-pyrimidinediamine;
XII-13: N4-(1-Cyclopropylmethyl-3-methyl-1H-indazol-6-yl)-5-methyl-N2-[4-methyl-3-(N-methylaminosulfonyl)phenyl]-2,4-pyrimidinediamine;
XIII-1: N4-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-fluoro-N2-[4-Aminosulfonyl)phenyl]-2,4-pyrimidinediamine;
XIII-2: N4-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-fluoro-N2-[3-Aminosulfonyl)phenyl]-2,4-pyrimidinediamine;
XIII-3: 5 N4-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-fluoro-N2-[4-methyl-3-aminosulfonyl)phenyl]-2,4-pyrimidinediamine;
XIII-4: N4-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-N4-methyl-5-fluoro-N2-[4-Aminosulfonyl)phenyl]-2,4-pyrimidinediamine;
XIII-5: N4-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-N4-methyl-5-fluoro-N2-[3-Aminosulfonyl)phenyl]-2,4-pyrimidinediamine;
XIII-6: N4-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-N4-methyl-5-fluoro-N2-[4-methyl-3-aminosulfonyl)phenyl]-2,4-pyrimidinediamine;
XIV-1: N4-(3-acetamido-2,3-dihydro-1H-indenyl)-5-methyl-N2-[3-Aminosulfonyl)phenyl]-2,4-pyrimidinediamine;
XIV-2: N4-(3-acetamido-2,3-dihydro-1H-indenyl)-5-methyl-N2-[4-Aminosulfonyl)phenyl]-2,4-pyrimidinediamine;
XV-1: N2-(3-Aminosulfonylphenyl)-6-fluoro-N4-(3-oxo-2,2,4-trimethylbenzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
XV-2: N2-(4-Aminosulfonylphenyl)-6-fluoro-N4-(3-oxo-2,2,4-trimethylbenzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
XV-3: N2,N6-Bis(4-aminosulfonylphenyl)-N4-(3-oxo-2,2,4-trimethylbenzo[1,4]oxazin-6-yl)-2,4,6-pyrimidinetriamine;
XV-4: N2-(4-Aminosulfonylphenyl)-5,6-dimethyl-N4-(3-oxo-2,2,4-trimethylbenzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
XV-5: N2-(3-Aminosulfonylphenyl)-6-fluoro-5-methyl-N4-(3-oxo-2,2,4-trimethylbenzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
XV-6: N2-(3-Aminosulfonylphenyl)-6-methyl-N4-[4-(3-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
XV-7: 3-Aminosulfonyl-4-methylphenyl)-6-methyl-N4-[4-(3-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
XV-8: N2-[4-(N-Cyclopropylaminosulfonyl)phenyl]-6-methyl-N4-[4-(3-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
XV-9: N2-(4-Aminosulfonylphenyl)-6-methyl-N4-[4-(3-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
XV-10: N2-(3-Aminosulfonylphenyl)-6-methyl-N4-[4-(2-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
XV-11: N2-(4-Aminosulfonylphenyl)-6-methyl-N4-[4-(2-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
XV-12: N2-[3-(N-Cyclopropylaminosulfonyl)phenyl)]-6-methyl-N4-[4-(2-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
XV-13: N2-(3-Aminosulfonyl-4-methylphenyl)-6-methyl-N4-[4-(2-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
XV-14: N2-[4-(N-Cyclopropylaminosulfonyl)phenyl]-6-methyl-N4-[4-(2-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
XV-15: 6-Methyl-N2-[4-methyl-3-(N-methylaminosulfonyl)phenyl]-N4-[4-(2-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
XV-16: N2-[3-(N-Cyclopropylaminosulfonyl)phenyl]-6-methyl-N4-[4-(3-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine;
XV-17: 6-Methyl-N2-[4-methyl-3-(N-methylaminosulfonyl)phenyl]-N4-[4-(3-pyridinylmethyleneoxy)phenyl]-2,4-pyrimidinediamine; and
XV-18: N2-(3-Aminosulfonylphenyl)-5,6-dimethyl-N4-(3-oxo-2,2,4-trimethylbenzo[1,4]oxazin-6-yl)-2,4-pyrimidinediamine;
or a solvate, prodrug or pharmaceutically acceptable salt thereof.
7 . A method of inhibiting an activity of a JAK kinase, comprising contacting the JAK kinase with an amount of a compound effective to inhibit an activity of the JAK kinase wherein the compound is selected from the compounds of any one of claims 1 to 6 .
8 . A method of inhibiting an activity of a JAK kinase, comprising contacting in vitro a JAK3 kinase with an amount of a compound effective to inhibit an activity of the JAK kinase wherein the compound is selected from the compounds of any one of claims 1 to 6 .
9 . A method of treating a T-cell mediated autoimmune disease, comprising administering to a patient suffering from such an autoimmune disease an amount of a compound effective to treat the autoimmune disease wherein the compound is selected from the compounds of any one of claims 1 to 6 .
10 . The method of claim 9 in which the compound is administered in combination with, or adjunctively to, a compound that inhibits Syk kinase with an IC 50 of about 10 μM or less.
11 . A method of treating or preventing allograft transplant rejection in a transplant recipient, comprising administering to the transplant recipient an amount of a compound effective to treat or prevent the allograft transplant rejection wherein the compound is selected from the compounds of any one of claims 1 to 6 .
12 . The method of claim 11 , wherein the compound is administered to a tissue or an organ prior to transplanting the tissue or organ in the allograft transplant recipient
13 . The method of claim 11 in which the allograft transplant rejection is acute rejection.
14 . The method of claim 11 in which the allograft transplant rejection is chronic rejection.
15 . The method of claim 11 in which the allograft transplant rejection is mediated by HVGR or GVHR.
16 . The method of claim 11 in which the transplant recipient receives an allograft transplant organis selected from a kidney, a heart, a liver and a lung.
17 . The method of claim 11 in which the compound is administered in combination with, or adjunctively to, an immunosuppressant.
18 . The method of claim 17 in which the immunosuppressant is selected from cyclosporine, tacrolimus, sirolimus, an inhibitor of IMPDH, mycophenolate, mycophanolate mofetil, an anti-T-Cell antibody and OKT3.
19 . A method of treating or preventing a Type IV hypersensitivity reaction, comprising administering to a subject an amount of a compound of effective to treat or prevent the hypersensitivity reaction wherein the compound is selected from the compounds of any one of claims 1 to 6 .
20 . The method of claim 18 which is practical prophylactically, and the compound selected from the compounds of any one of claims 1 to 6 .
21 . A method of inhibiting a signal transduction cascade in which JAK3 kinase plays a role, comprising contacting a cell expressing a receptor involved in said signaling cascade with a compound wherein the compound is selected from the compounds of any one of claims 1 to 6 .
22 . A method of treating or preventing a JAK kinase-mediated disease, comprising administering to a subject an amount of compound effective to treat or prevent the JAK kinase-mediated disease wherein the compound is selected from the compounds of any one of claims 1 to 6 .
23 . The method of claim 22 in which the JAK kinase-mediated disease is HVGR or GVHR.
24 . The method of claim 22 in which the JAK kinase-mediated disease is acute allograft rejection.
25 . The method of claim 22 in which the JAK kinase-mediated diseases is chronic allograft rejection.
26 . A pharmaceutical formulation comprising a compound selected from the compounds of any one of claims 1 to 6 .
27 . A kit comprising a compound selected from the compounds of any one of claims 1 to 6 or a prodrug thereof, packaging and instructions for use.
28 . A kit comprising the pharmaceutical formulation of claim 27 , packaging, and instructions for use.Join the waitlist — get patent alerts
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