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US 9,872,852 B2Granted
Compounds useful as immunomodulators
AssigneeBristol-Myers Squibb Company
InventorsLouis S. Chupak, Xiaofan Zheng
Life of this patent
Estimating the term…
Abstract
Disclosed are compounds of Formula (I): (I). Also disclosed are methods of using such compounds as immunomodulators, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing the progression of virological diseases or disorders and cancer.
Claims11
A compound of Formula (I):
- or salts thereof, wherein:
- Ring B is phenyl or thienyl;
- Ring A is:
- wherein A″ is CH or N, and wherein one of R1 and R2 is Q and the other of R1 and R2 is Rb;
- R3 is H or —CH2C(O)OH;
- R4 is —NHCH2CH2NHC(O)CH3;
- Q is:
- (i)
- wherein Ry is —OH, —CH3, —CH2OH, —C(O)OH, —CH2C(O)OH, or —C(O)NHCH2CH2OH, —C(O)NH2, —NHC(O)CH3, and Rz is —OH, —CH3, —OCH3, —OC(O)CH3, or —CH2CH═CH2 and Rh is —CH3 or —C(O)CH3;
- (ii) —CH2NH—Rx wherein Rx is cyclobutyl, —(CH2)cyclobutyl optionally substituted with two fluorine atoms, cyclopropyl, hydroxycyclopentyl, cyclopentyl, cyclohexyl, hydroxycyclohexyl, hydroxytetrahydrofuranyl, N-methyl piperidinyl, N-ethyl piperidinyl, hydroxytetrahydrothienyl, or
- (iii) —CH2NRa—CRaRa—(CH2)n—Rx wherein Rx is hydrogen, azetidinonyl, cyclohexyl, hydroxyphenyl, pyrrolidinonyl, piperidinonyl, piperazinonyl, morpholinyl, imidazolyl, N-methylimidazolyl, —C(O)(morpholinyl), piperazinyl optionally substituted with a methyl, phenyl, alkoxyphenyl, hydroxyphenyl, pyridinyl, pyrimidinyl, or —C(O)OC(CH3)3 group, pyrrolidinyl, pyridinyl, thiomorpholine dioxide, or methyl triazolyl;
- or
- (iv) —CHRa—NRa—CRaRa—(CHRa)n—Rx wherein Rx is —OH, —OCH3, —C(O)OH, —OPh, —CH(CO2H)—NHC(O)CH3, —O(CH2)2O(CH2)2OH, —O(CH2)2O(CH2)2O(CH2)2OH, —O(CH2)2O(CH2)2O(CH2)2O(CH2)2CO2H—O(CH2)2O(CH2)2O(CH2)2O(CH2)2O(CH2)2O(CH2)2CO2H, —C(O)CH3, —C(O)NRaRa, —C(O)NRqRq, —N(CH3)2, —NHC(O)CH3, —NHC(O)Ph, —C(O)NH(CH2)2-imidazolyl, NHC(O)OCH2Ph, —N(CH3)S(O)2CH3, —NHC(O)CH═CH2, —NHC(O)CH═CHC(O)CH2CH3, —NHS(O)2CH3, or
- each Ra is independently H, —CH(OH)CH3, OH, —(CH2)2OH, —CH2OH, —(CH2)2NH2, —CH2CH3, or —CH3;
- or, two Ra groups on the same carbon atom can form a four, five-, or six-membered carbocyclic ring, an N-methylpiperidinyl ring, or a pyranyl ring;
- each Rb is independently H, F, Cl, Br, —CF3, —CN, CH3, or —OCH3;
- each Rc is independently —OCH3, —OH, —OCH2CH3, —O(CH2)OCH3, —OCH2CH═CH2, —O(CH2)2CH3, —O(CH2)2-morpholinyl, or F;
- or two Rc attached to adjacent carbon atoms form —O—(CH2)v—O—, wherein v is 1 or 2;
- each Rq is selected from hydrogen, —CH2C(O)NHCH2CO2H, —(CH2)C(O)NHCH(CO2H)CH2CH(CH3)2, —CH(Bn)-C(O)NHCH(CO2H)(CH2)3NHC(NH)NH2;
- m is zero or 1;
- n is zero, 1, 2, or 3;
- each p is independently zero or 1;
- and
- q is zero, 1, or 2.
21 more elements
Dependencies are inferred from the claim text.