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US 8,309,737 B2Granted
Phosphinate ruthenium complexes
AssigneeIdenix Pharmaceuticals, Inc.
InventorsChristophe Claude Parsy, Francois-Rene Alexandre, Florence Marie-Emilie Bonnaterre, Dominique Surleraux
Life of this patent
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Abstract
Provided herein are ruthenium complexes of Formula (I), and processes of preparation thereof. Also provided are methods of their use as a metathesis catalyst.
Claims38
A ruthenium complex of Formula I:
- wherein:
- L is a neutral ligand;
- R1 is C1-12 alkyl, C3-10 cycloalkyl, C6-14 aryl, heteroaryl, heterocyclyl, or —NR3bR3c;
- R2 is H, C1-12 alkyl, C3-10 cycloalkyl, or C6-14 aryl;
- R3 is halo, cyano, nitro, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-7 cycloalkyl, C6-14 aryl, heteroaryl, heterocyclyl, —C(O)R3a, —C(O)OR3a, —C(O)NR3bR3c, —OR3a, —NR3bR3c, —NR3aC(O)R3b, —NR3aC(O)OR3b, —NR3aS(O)2R3b, —PR3aR3b, —P(OR3a)R3b, —P(OR3a)(OR3b), —P(O)R3aR3b, —P(O)(OR3a)R3b, —P(O)(OR3a)(OR3b),—S(O)2R3a, or —SO2NR3bR3c,
- R4 is C1-12 alkyl, C3-10 cycloalkyl, C7-15 aralkyl, or —C(R4aR4b)C(O)NR4cR4d;
- R5 is hydrogen, C1-12 alkyl, C2-12 alkenyl, C2-12 alkynyl, C3-10 cycloalkyl, or C6-14 aryl;
- each R3a and R3d is independently hydrogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-7 cycloalkyl, C6-14 aryl, heteroaryl, or heterocyclyl;
- each R3b and R3c is independently hydrogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-7 cycloalkyl, C6-14 aryl, heteroaryl, or heterocyclyl;
- or R3b and R3c together with the N atom form a heteroaryl or heterocyclyl;
- R4a and R4b are each independently hydrogen, C1-6 alkyl, C3-8 cycloalkyl, C6-14 aryl, or C7-15 aralkyl;
- R4c and R4d are each independently hydrogen, C1-6 alkyl, C3-8 cycloalkyl, C6-14 aryl, or C7-15 aralkyl;
- or R4c and R4d together with the N atom form heterocyclyl;
- X1 and X2 are each independently an anionic ligand;
- Y is a bond or —NRb—;
- Z is O or S;
- and
- n is an integer of 0, 1, 2, or 3;
- wherein each alkyl, alkenyl, alkynyl, aryl, aralkyl, cycloalkyl, heterocyclyl, and heteroaryl is optionally substituted with one or more groups, each independently selected from (a) cyano, halo, or nitro;
- (b) C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-7 cycloalkyl, C6-14 aryl, C7-15 aralkyl, heteroaryl, or heterocyclyl, each optionally substituted with one or more substituents Q;
- or (c) —C(O)Ra, —C(O)ORa, —C(O)NRbRc, —C(NRa)NRbRc, —ORa, —OC(O)Ra, —OC(O)ORa, —OC(O)NRbRc, —OC(═NRa)NRbRc, —OS(O)Ra, —OS(O)2Ra, —OS(O)NRbRc, —OS(O)2NRbRc, —NRbRc, —NRaC(O)Rd, —NRaC(O)ORd, —NRaC(O)NRbRc, —NRaC(═NRd)NRbRc, —NRaS(O)Rd, —NRaS(O)2Rd, —NRaS(O)NRbRc, —NRaS(O)2NRbRc, —PRaRd, —P(ORa)Rd, —P(ORa)(ORd), —P(O)RaRd, —P(O)(ORa)Rd, —P(O)(ORa)(ORd), —SRa, —S(O)Ra, —S(O)2Ra, or —SO2NRbRc;
- wherein each Ra, Rb, Rc, and Rd is independently hydrogen;
- C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-7 cycloalkyl, C6-14 aryl, C7-15 aralkyl, heteroaryl, or heterocyclyl, each optionally substituted with one or more substituents Q;
- or Rb and Rc together with the N atom to which they are attached form heterocyclyl, optionally substituted with one or more substituents Q;
- wherein each Q is independently selected from the group consisting of (i) cyano, halo, or nitro;
- (ii) C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-7 cycloalkyl, C6-14 aryl, C7-15 aralkyl, heteroaryl, or heterocyclyl;
- or (iii) —C(O)Re, —C(O)ORe, —C(O)NRfRg, —C(NRe)NRfRg, —ORe, —OC(O)Re, —OC(O)ORe, —OC(O)NRfRg, —OC(═NRe)NRfRg, —OS(O)Re, —OS(O)2Re, —OS(O)NRfRg, —OS(O)2NRfRg, —NRfRg, —NReC(O)Rh, —NReC(O)ORh, —NReC(O)NRfRg, —NReC(═NRh)NRfRg, —NReS(O)Rh, —NReS(O)2Rh, —NReS(O)NRfRg, —NReS(O)2NRfRg, —PReRh, —P(ORe)Rh, —P(ORe)(ORh), —P(O)ReRh, —P(O)(ORe)Rh, —P(O)(ORe)(ORh), —SRe, —S(O)Re, —S(O)2Re, or —S(O)2NRfRg;
- wherein each Re, Rf, Rg, and Rh is independently hydrogen;
- C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-7 cycloalkyl, C6-14 aryl, C7-15 aralkyl, heteroaryl, or heterocyclyl;
- or Rf and Rg together with the N atom to which they are attached form heterocyclyl.
27 more elements
Dependencies are inferred from the claim text.