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US 6,713,462 B2Granted
Quinolinones and uses thereof
AssigneeARIAD Pharmaceuticals, Inc.
InventorsChester A. Metcalf, III, William C. Shakespeare, Tomi K. Sawyer, Yihan Wang, Regine Bohacek, Rajeswari Sundaramoorthi
Life of this patent
Estimating the term…
Abstract
The invention relates to compounds of the general formula (and pharmaceutically acceptable derivatives thereof): in which RA, RB, RC, RD, R5, R7, R9, R9a, AK, p, q, r and X are as defined herein, and to their preparation and use.
Claims75
A compound having the structure (and pharmaceutically acceptable derivatives thereof):
- wherein the dotted line represents an optional bond;
- X is O, S or NRH;
- RA is hydrogen, oxygen, or an aliphatic, heteroaliphatic, aryl or heteroaryl moiety;
- RB is an aliphatic, heteroaliphatic, aryl or heteroaryl moiety;
- RC is hydrogen;
- aliphatic;
- heteroaliphatic;
- aryl;
- heteroaryl;
- halogen;
- cyano;
- alkyloxycarbonyl;
- or —ZRJ, wherein each occurrence of Z is independently —O—, —S—, NRK, —C(O)—, —S(O)2—, or —COO—, wherein each occurrence of RJ and RK is independently hydrogen, CORL, COORL, CONRLRM, 13 CO(NORL)RM, —CH═NORJ, —NRLRM, —S(O)2RL, —P(O)(ORL)RM, or an aliphatic, heteroaliphatic, aryl or heteroaryl moiety, and wherein each occurrence of RL and RM is independently hydrogen, or an aliphatic, heteroaliphatic, aryl or heteroaryl moiety;
- RD is an aryl or heteroaryl moiety;
- each occurrence of R9 and R5 is independently hydrogen;
- aliphatic;
- heteroaliphatic;
- aryl;
- heteroaryl;
- cyano;
- —C(O)RJ;
- —C(O)ORJ;
- —NRJC(O)ORK;
- —OC(O)RJ;
- —NRJSO2RK;
- —SO2NRJRK;
- —NRJC(O)RK;
- —C(O)NRJRK;
- —CH═NORJ;
- —S(O)nRJ, wherein n is an integer from 0 to 2;
- —(CRLCRM)u—C≡CRJ;
- or —ZRJ, wherein each occurrence of Z is independently —O—, —S—, NRK, —C(O)—, —S(O)2—, or —COO—, wherein each occurrence of RJ and RK is independently hydrogen, CORL, COORL, CONRLRM, —CO(NORL)RM, —CH═NORJ, —NRLRM, —S(O)2RL, —P(O)(ORL)RM, or an aliphatic, heteroaliphatic, aryl or heteroaryl moiety;
- R7 is hydrogen;
- aliphatic;
- heteroaliphatic;
- aryl;
- heteroaryl;
- cyano;
- —C(O)RJ;
- —C(O)ORJ;
- —NRJC(O)ORK;
- —OC(O)RJ;
- —NRJSO2RK;
- —SO2NRJRK;
- —NRJC(O)RK;
- —C(O)NRJRK;
- —CH═NORJ;
- —S(O)nRJ, wherein n is an integer from 0 to 2;
- —(CRLCRM)u—C≡CRJ;
- or —ZRJ, wherein each occurrence of Z is independently —O—, —S—, NRK, —C(O)—, —S(O)2—, or —COO—, wherein each occurrence of RJ and RK is independently hydrogen, CORL, COORL, CONRLRM, —CO(NORL)RM, —CH═NORJ, —NRLRM, —S(O)2RL, —P(O)(ORL)RM, or an aliphatic, heteroaliphatic, aryl or heteroaryl moiety;
- u is an integer from 0-6;
- AK is (CRPCRQ);
- each occurrence of RP and RQ is independently hydrogen or an aliphatic moiety;
- q is an integer from 0 to 5;
- p is an integer from 0-3;
- r is an integer from 0-2;
- R9a is hydrogen;
- or an aliphatic or heteroaliphatic moiety;
- wherein in each of the foregoing groups each aliphatic or heteroaliphatic moiety may be branched or unbranched, cyclic or acyclic and substituted or unsubstituted, and may contain one or more electronically unsaturated bonds, and each aryl and heteroaryl moiety may be substituted or unsubstituted;
- and
- at least one of RB or RD as defined above, comprises a phosphorus-containing moiety.
58 more elements
Dependencies are inferred from the claim text.