IP Library Granted Patent US 9,464,082
Granted Patent B2
US 9,464,082 · App. 14/604,129 · Granted Oct 11, 2016

Aryl and arylalkyl substituted pyrazolyl and pyrimidinyl tricyclic enones as antioxidant inflammation modulators

Inventors: Pamela Donner (Mundelein, IL); Rolf Wagner (Antioch, IL); Jason Shanley (Chicago, IL); Howard Heyman (Deerfield, IL); Allan Krueger (Gurnee, IL); Hui-Ju Chen (Grayslake, IL); Michael Rozema (Kenosha, WI); David Grampovnik (Waukegan, IL); Melean Visnick (Irving, TX); Eric Anderson (Southlake, TX); Xin Jiang (Coppell, TX); Christopher F. Bender (Garland, TX); Gary Louis Bolton (Ann Arbor, MI); Bradley William Caprathe (Livonia, MI); Chitase Lee (Ann Arbor, MI); William Howard Roark (Ann Arbor, MI)
Assignees: AbbVie Inc.; Reata Pharmaceuticals, Inc.
C07D471/04C07D231/54C07D239/70C07D239/72C07D401/04C07D403/04C07D413/04C07D417/04
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Quick Facts
Patent No.
US 9,464,082
App. No.
14/604,129
Granted
Oct 11, 2016
Kind
B2
Abstract

The present application relates to: (a) compounds of Formula (I): and salts thereof, wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , m, n, X and Y are as defined in the specification; (b) compositions comprising such compounds and salts; and (c) methods of use of such compounds, salts, and compositions, particularly use for the treatment and prevention of diseases such as those associated with oxidative stress and inflammation.

Claims (345)

1. A compound of Formula (I),

or a pharmaceutically acceptable salt thereof, wherein

is a single or double bond;

m is 0 or 1;

n is 1 or 2;

p is 1, 2, or 3;

q is 1, 2, or 3;

r is 1, 2, 3, or 4;

X is NC—, F 3 C—, R 1x C(O)—, or O 2 N—;

Y is G 1 -, G 1 -(CR a R b )—, G 2 -, or G 2 -(CR a R b )—;

R 1 and R 2 are each independently hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, amido, amino, halogen, hydroxy, G R1a -, G R1a -(CR a R b ) p —, G R1b -, R 1a C(O)—, (R 1a ) 2 N—, G R1a NH—, G R1a -(CR a R b ) p —NH—, G R1a O—, and R 1a CO 2 —; or

R 1 and R 2 joined together with the carbon atom to which they are attached form a C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, or 4-6-membered heterocycle optionally substituted with C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, cyano, halogen, hydroxy, Or oxo;

R 3 is absent, hydrogen, C 1 -C 6 -alkyl, C 2 -C 4 -alkenyl, C 1 -C 6 -fluoroalkyl, G 3a - or G 3a -(CR a R b ) q —; provided that R 3 is absent when and only when the atom to which it is attached forms part of a double bond;

R 4 is hydrogen, C 1 -C 6 -alkyl, C 2 -C 4 -alkenyl, C 1 -C 6 -fluoroalkyl, amino, C 1 -C 6 -alkylamino, C 1 -C 6 -dialkylamino, C 1 -C 6 -alkoxy, cyano, halogen, hydroxy, G 4a -, G 4b -, G 4a -(CR a R b ) p —, G 4b -(CR a R b ) p —, G 4a O— or G 4a NH—;

R 5 is absent, hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -fluoroalkyl, G R5a -, G R5a -(CR a R b )—, R 5a C(O)—, G R5a C(O)—, hydroxy-C 1 -C 6 -alkyl-C(O)—, R 5a O 2 C—, G R5a O 2 C—, G R5a HNC(O)—, R 5a O 2 CNHCH 2 C(O)—, H 2 NHCH 2 C(O)—, R 5a SO 2 —, or G R5a SO 2 —; provided that R 5 is absent when and only when the atom to which it is attached forms part of a double bond;

R 6 is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, amino, C 1 -C 6 -alkylamino, C 1 -C 6 -dialkylamino, hydroxy, G 6a -, G 6a N(R a )—, G 6a O— or G 6b -;

R a and R b are, at each occurrence, independently hydrogen, C 1 -C 6 -alkyl, or C 1 -C 6 -haloalkyl;

R 1a is, at each occurrence, independently hydrogen, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl or C 1 -C 4 -haloalkyl;

R 1x is hydroxy, C 1 -C 6 -alkoxy, amino, C 1 -C 6 -alkylamino, C 1 -C 6 -dialkylamino, or C 1 -C 6 -alkylsulfonylamino;

R G1a is, at each occurrence, independently hydrogen, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl or C 1 -C 4 -haloalkyl;

R G1b is, at each occurrence, independently C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl or C 1 -C 4 -haloalkyl;

R G2a is, at each occurrence, independently hydrogen, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl or C 1 -C 4 -haloalkyl;

R G2b is, at each occurrence, independently C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl or C 1 -C 4 -haloalkyl;

R G4a is, at each occurrence, independently C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl or C 1 -C 4 -haloalkyl;

R 5a is, at each occurrence, independently hydrogen, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl or C 1 -C 4 -haloalkyl;

R G6a is, at each occurrence, independently C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl or C 1 -C 4 -haloalkyl;

R G6b is, at each occurrence, independently hydrogen, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl or C 1 -C 4 -haloalkyl;

R G6c is, at each occurrence, independently C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl or C 1 -C 4 -haloalkyl;

R G6d is, at each occurrence, independently hydrogen, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl or C 1 -C 4 -haloalkyl;

G 1 is phenyl optionally substituted with 1, 2, 3, 4 or 5 C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, carboxy, cyano, cyano-C 1 -C 6 -alkyl, halogen, halo-C 1 -C 6 -alkyl, hydroxy, hydroxy-C 1 -C 6 -alkyl, R G1b O 2 C—, R G1a HN(O)C—, (R G1a ) 2 N(O)C—, G 1a C(O)—, G 1b HN(O)C—, G 1b -, R G1a C(O)N(R G1a )—, R G1b (O)CN(R G1a )—, R G1b O2SN(R G1a )—, (R G1a ) 2 N—, G 1b O—, G 1b CH 2 O—, R G1a CO 2 —, (R G1a ) 2 NCO 2 —, HS—, R G1b S—, R G1b S(O)—, R G1b SO 2 — or (R G1a ) 2 NSO 2 —;

G 2 is a 5-6-membered heteroaryl optionally substituted with 1, 2, 3, 4 or 5 C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, carboxy, cyano, cyano-C 1 -C 6 -alkyl, halogen, halo-C 1 -C 6 -alkyl, hydroxy, hydroxy-C 1 -C 6 -alkyl, R G2b CO 2 —, R G2a HNC(O)—, (R G2a ) 2 NC(O)—, G 2a C(O)—, G 2b HNC(O)—, G 2b -, R G2a C(O)N(R G2a )—, R G2b OC(O)N(R G2a )—, R G2b SO 2 N(R G2a )—, (R G2a ) 2 N—, G 2b O—, G 2b CH 2 O—, R G2a CO 2 —, (R G2a ) 2 NCO 2 —, HS—, R G2b S—, R G2b S(O)—, R G2b SO 2 —, or (R G2a ) 2 NSO 2 —;

G 1a is a 4-6-membered heterocycle optionally substituted with 1, 2, 3 or 4 C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, cyano, halogen, hydroxy, or oxo;

G 1b is phenyl or 5-6-membered heteroaryl optionally substituted with 1, 2, 3, 4 or 5 C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, cyano, halogen, hydroxy, or nitro;

G R1a is phenyl or 5-6-membered heteroaryl optionally substituted with 1, 2, 3, 4 or 5 C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, cyano, halogen, hydroxy, or nitro;

G R1b is a 4-6-membered heterocycle optionally substituted with 1, 2, 3 or 4 C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, cyano, halogen, hydroxy, or oxo;

G 2a is a 4-6-membered heterocycle optionally substituted with 1, 2, 3 or 4 C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, cyano, halogen, hydroxy, or oxo;

G 2b is phenyl or 5-6-membered heteroaryl optionally substituted with 1, 2, 3, 4 or 5 C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, cyano, halogen, hydroxy, or nitro;

G 3a is phenyl or 5-6-membered heteroaryl optionally substituted with 1, 2, 3, 4 or 5 C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, cyano, halogen, or hydroxy;

G 4a is phenyl or 5-6-membered heteroaryl optionally substituted with 1, 2, 3, 4 or 5 C 1 -C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, amido, carboxy, cyano, halogen, hydroxy, R G4a O 2 C—, R G4a C(O)—, (R G4a ) 2 NC(O)—, or G 4a1 -;

G 4a1 is phenyl or 5-6-membered heteroaryl optionally substituted with 1, 2, 3, 4 or 5 C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, cyano, halogen, hydroxy, or nitro;

G 4b is a 4-6-membered heterocycle optionally substituted with 1, 2, 3 or 4 C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, cyano, halogen, hydroxy, or oxo;

G R5a is phenyl or 5-6-membered heteroaryl optionally substituted with 1, 2, 3, 4 or 5 C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, cyano, halogen, hydroxy, or nitro;

G 6a is C 6 -C 10 -aryl or 5-10-membered heteroaryl optionally substituted with 1, 2, 3, or 4 C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, amino, C 1 -C 6 -alkylsulfonylamino, carboxy, halogen, hydroxy, hydroxyC 1 -C 6 -alkyl, R G6a C(O)—, R G6a O 2 C—, HO 2 C—(CR a R b ) r —, R G6a O 2 C—(CR a R b ) r —, (R G6b ) 2 N(O)C—(CR a R b ) r —, R G6a CO 2 —(CR a R b ) r —, G 6c -, or G 6d -;

G 6b is 4-6-membered heterocycle optionally substituted with 1, 2, 3, or 4 C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy, cyano, halogen, hydroxy, or oxo;

G 6c is phenyl or 5-6-membered heteroaryl optionally substituted with 1, 2, 3, or 4 C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy, amino, C 1 -C 6 -alkylsulfonylamino, di(C 1 -C 6 -alkylsulfonyl)amino, C 1 -C 6 -alkylsulfonylaminoC 1 -C 6 -alkyl, carboxy, cyano, halogen, hydroxy, hydroxyC 1 -C 6 -alkyl, R G6c C(O)—, R G6c O 2 C—, (R G6d ) 2 NC(O)—, HO 2 C—(CR a R b ) r —, R G6c O 2 C—(CR a R b ) r —, (R G6d ) 2 NC(O)—(CR a R b ) r —, or R G6c CO 2 —(CR a R b ) r —; and

G 6d is 4-6-membered heterocycle optionally substituted with 1, 2, 3, or 4 C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy, cyano, halogen, hydroxy, or oxo.

2. The compound of claim 1 , or salt thereof, further defined by the Formula (Ia).

3. The compound of claim 2 , or salt thereof, further defined by the Formula (Ia-1).

4. The compound of claim 3 , or salt thereof, wherein

X is NC— or R 1x C(O)—;

Y is G 1 - or G 1 -(CR a R b )—; and

R 1x is hydroxy, C 1 -C 6 -alkoxy, amino, C 1 -C 6 -alkylamino, C 1 -C 6 -dialkylamino, or C 1 -C 6 -alkylsulfonylamino.

5. The compound of claim 4 , or salt thereof, wherein

X is NC—; and

Y is G 1 -.

6. The compound of claim 5 , or salt thereof, wherein

r is 1, 2, or 3;

R 4 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkylamino, C 1 -C 6 -dialkylamino, C 1 -C 6 -alkoxy, halogen, G 4a -, G 4b -, or G 4a NH—;

R 6 is hydrogen, C 1 -C 6 -alkoxy, hydroxy, G 6a -, G 6a N(R a )— or G 6b -;

R a and R b are, at each occurrence, hydrogen;

R G1a is, at each occurrence, independently hydrogen or C 1 -C 4 -alkyl;

R G1b is, at each occurrence, C 1 -C 4 -alkyl;

R G4a is, at each occurrence, C 1 -C 4 -alkyl;

R G6a is, at each occurrence, C 1 -C 4 -alkyl;

R G6b is, at each occurrence, hydrogen;

R G6c is, at each occurrence, C 1 -C 4 -alkyl;

R G6d is, at each occurrence, hydrogen;

G 1 is phenyl optionally substituted with 1 C 1 -C 6 -alkyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, carboxy, halogen, hydroxy, hydroxy-C 1 -C 6 -alkyl, R G1b O 2 C—, R G1a HN(O)C—, (R G1a ) 2 N(O)C—, G 1a C(O)—, G 1b HN(O)C—, or G 1b CH 2 O—;

G 1a is a 4-6-membered heterocycle;

G 1b is phenyl;

G 4a is phenyl or 5-6-membered heteroaryl optionally substituted with 1 or 2 C 1 -C 6 -alkyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, amido, carboxy, halogen, hydroxy, R G4a O 2 C—, (R G4a ) 2 NC(O)—, or G 4a1 -;

G 4a1 is 5-6-membered heteroaryl optionally substituted with 1 C 1 -C 6 -alkyl;

G 4b is a 4-6-membered heterocycle;

G 6a is C 6 -C 10 -aryl or 5-10-membered heteroaryl optionally substituted with 1 or 2 C 1 -C 6 -alkyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, amino, halogen, hydroxy, hydroxyC 1 -C 6 -alkyl, R G6a C(O)—, R G6a O 2 C—, HO 2 C—(CR a R b ) r —, R G6a O 2 C—(CR a R b ) r —, (R G6b ) 2 N(O)C—(CR a R b ) r —, R G6a CO 2 —(CR a R b ) r —, G 6c -, or G 6d -;

G 6b is 4-6-membered heterocycle optionally substituted with 1 or 2 C 1 -C 6 -alkyl or oxo;

G 6c is phenyl or 5-6-membered heteroaryl optionally substituted with 1 or 2 C 1 -C 6 -alkyl, amino, C 1 -C 6 -alkylsulfonylamino, halogen, hydroxy, R G6c O 2 C—, or (R G6d ) 2 NC(O)—; and

G 6d is 4-6-membered heterocycle.

7. The compound of claim 4 , or salt thereof, wherein

X is R 1x C(O)—;

Y is G 1 -; and

R 1x is amino.

8. The compound of claim 7 , or salt thereof, wherein

R 4 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, or halogen;

R 6 is hydrogen, C 1 -C 6 -alkoxy, hydroxy or G 6a -;

R G1b is, at each occurrence, C 1 -C 4 -alkyl;

G 1 is phenyl optionally substituted with 1 C 1 -C 6 -alkyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, halogen, hydroxy, or R G1b O 2 C—;

G 6a is C 6 -C 10 -aryl or 5-10-membered heteroaryl optionally substituted with 1 or 2 C 1 -C 6 -alkyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, halogen, hydroxy, or G 6c -; and

G 6c is phenyl or 5-6-membered heteroaryl optionally substituted with 1 C 1 -C 6 -alkyl or halogen.

9. The compound of claim 1 , or salt thereof, further defined by the Formula (Ib).

10. The compound of claim 9 , or salt thereof, further defined by the Formula (Ib-1).

11. The compound of claim 10 , or salt thereof, wherein

X is NC— or R 1x C(O)—;

Y is G 1 - or G 1 -(CR a R b )—; and

R 1x is hydroxy, C 1 -C 6 -alkoxy, amino, C 1 -C 6 -alkylamino, C 1 -C 6 -dialkylamino, or C 1 -C 6 -alkylsulfonylamino.

12. The compound of claim 11 , or salt thereof, wherein

X is NC—; and

Y is G 1 -.

13. The compound of claim 12 , or salt thereof, wherein

r is 1, 2 or 3;

R 5 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -fluoroalkyl, G R5a -, G R5a -(CR a R b )—, R 5a C(O)—, G R5a C(O)—, hydroxy-C 1 -C 6 -alkyl-C(O)—, R 5a O 2 C—, G R5a O 2 C—, G R5a HNC(O)—, R 5a O 2 CNHCH 2 C(O)—, H 2 NHCH 2 C(O)—, R 5a SO 2 —, or G R5a SO 2 —;

R 6 is hydrogen, C 1 -C 6 -alkoxy, or G 6a -;

R a and R b are, at each occurrence, hydrogen;

R G1b is, at each occurrence, C 1 -C 4 -alkyl;

R 5a is, at each occurrence, C 1 -C 4 -alkyl;

R G6d is, at each occurrence, hydrogen;

G 1 is phenyl optionally substituted with 1 or 2 C 1 -C 6 -alkyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, carboxy, halogen, hydroxy, or R G1b O 2 C—;

G R5a is phenyl or 5-6-membered heteroaryl;

G 6a is C 6 -C 10 -aryl or 5-10-membered heteroaryl optionally substituted with 1 or 2 C 1 -C 6 -alkyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, amino, C 1 -C 6 -alkylsulfonylamino, carboxy, halogen, hydroxy, hydroxyC 1 -C 6 -alkyl, HO 2 C—(CR a R b ) r — or G 6c -; and

G 6c is phenyl or 5-6-membered heteroaryl optionally substituted with 1 or 2 C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, amino, C 1 -C 6 -alkylsulfonylamino, di(C 1 -C 6 -alkylsulfonyl)amino, C 1 -C 6 -alkylsulfonylaminoC 1 -C 6 -alkyl, carboxy, cyano, halogen, hydroxy, hydroxyC 1 -C 6 -alkyl, and (R G6d ) 2 NC(O)—.

14. The compound of claim 11 , or salt thereof, wherein

X is NC— or R 1x C(O)—;

Y is G 1 -(CR a R b )—;

R 5 is hydrogen, C 1 -C 6 -alkyl, R 5a C(O)— or R 5a SO 2 —;

R 6 is hydrogen or G 6a -;

R a and R b are, at each occurrence, hydrogen;

R 1x is amino;

R 5a is, at each occurrence, C 1 -C 4 -alkyl;

G 1 is phenyl optionally substituted with 1 or 2 C 1 -C 6 -alkyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, carboxy, halogen, hydroxy, or R G1b O 2 C—; and

G 6a is C 6 -C 10 -aryl or 5-10-membered heteroaryl optionally substituted with 1 or 2 C 1 -C 6 -alkyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylsulfonylamino, carboxy or halogen.

15. The compound of claim 1 , or salt thereof, further defined by the Formula (Ic).

16. The compound of claim 15 , or salt thereof, further defined by the Formula (IC-1).

17. The compound of claim 16 , or salt thereof, wherein,

q is 1;

X is NC—;

Y is G 1 -;

R 3 is hydrogen, C 1 -C 6 -alkyl, or G 3a -(CR a R b ) q —;

R 6 is hydrogen or G 6a -;

R a and R b are, at each occurrence, hydrogen;

R G1a is, at each occurrence, independently hydrogen or C 1 -C 4 -alkyl;

R G1b is, at each occurrence, C 1 -C 4 -alkyl;

G 1 is phenyl optionally substituted with 1 C 1 -C 6 -alkyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, carboxy, halogen, hydroxy, hydroxy-C 1 -C 6 -alkyl, R G1b O 2 C—, R G1a HN(O)C—, (R G1a ) 2 N(O)C—, G 1a C(O)—, G 1b HN(O)C—, or G 1b CH 2 O;

G 1a is a 4-6-membered heterocycle;

G 1b is phenyl;

G 3a is phenyl or 5-6-membered heteroaryl optionally substituted with 1 or 2 C 1 -C 6 -alkyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy or halogen; and

G 6a is C 6 -C 10 -aryl or 5-10-membered heteroaryl optionally substituted with 1 or 2 C 1 -C 6 -alkyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy or halogen.

18. The compound of claim 16 , or salt thereof, wherein,

q is 1;

X is NC—;

Y is G 1 -(CR a R b )—;

R 3 is hydrogen, C 1 -C 6 -alkyl, or G 3a -(CR a R b ) q —;

R 6 is hydrogen or G 6a -;

R a and R b are, at each occurrence, hydrogen;

R G1a is, at each occurrence, independently hydrogen or C 1 -C 4 -alkyl;

R G1b is, at each occurrence, C 1 -C 4 -alkyl;

G 1 is phenyl optionally substituted with 1 C 1 -C 6 -alkyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, carboxy, halogen, hydroxy, hydroxy-C 1 -C 6 -alkyl, R G1b O 2 C—, R G1a HN(O)C—, (R G1a ) 2 N(O)C—, G 1a C(O)—, G 1b HN(O)C—, or G 1b CH 2 O;

G 1a is a 4-6-membered heterocycle;

G 1b is phenyl;

G 3a is phenyl or 5-6-membered heteroaryl optionally substituted with 1 or 2 C 1 -C 6 -alkyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy or halogen; and

G 6a is C 6 -C 10 -aryl or 5-10-membered heteroaryl optionally substituted with 1 or 2 C 1 -C 6 -alkyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy or halogen.

19. The compound of claim 1 , or salt thereof, further defined by the Formula (Id).

20. The compound of claim 19 , or salt thereof, further defined by the Formula (Id-1).

21. The compound of claim 20 , or salt thereof, wherein,

X is NC—; and

Y is G 1 -;

r is 1, 2 or 3;

R 5 is hydrogen, C 1 -C 6 -alkyl, G R5a -(CR a R b )—, R 5a C(O)—, G R5a C(O)—, R 5a SO 2 —, or G R5a SO 2 —;

R 6 is hydrogen or G 6a -;

R a and R b are, at each occurrence, hydrogen;

R 5a is, at each occurrence, C 1 -C 4 -alkyl;

G 1 is phenyl optionally substituted with 1 or 2 C 1 -C 6 -alkyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, carboxy, halogen or hydroxy;

G R5a is phenyl or 5-6-membered heteroaryl;

G 6a is C 6 -C 10 -aryl or 5-10-membered heteroaryl optionally substituted with 1 or 2 C 1 -C 6 -alkyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkoxy, amino, C 1 -C 6 -alkylsulfonylamino, carboxy, halogen, hydroxy, hydroxyC 1 -C 6 -alkyl, HO 2 C—(CR a R b ) r — or G 6c -; and

G 6c is phenyl or 5-6-membered heteroaryl optionally substituted with 1 or 2 C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, amino, C 1 -C 6 -alkylsulfonylamino, di(C 1 -C 6 -alkylsulfonyl)amino, C 1 -C 6 -alkylsulfonylaminoC 1 -C 6 -alkyl, carboxy, cyano, halogen and hydroxy.

22. The compound of claim 1 , or a salt thereof, wherein the compound is selected from the group consisting of:

(6aS,7S,10aR)-7-methyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

rac-(5aS,6S,9aR)-2,6-dimethyl-7-oxo-3,9a-diphenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

rac-(5aS,6S,9aR)-1,6-dimethyl-7-oxo-3,9a-diphenyl-4,5,5a,6,7,9a-hexahydro-1H-benzo[g]indazole-8-carbonitrile;

rac-(5aS,6S,9aR)-9a-(4-methoxyphenyl)-2,6-dimethyl-7-oxo-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

rac-(5aS,6S,9aR)-9a-(4-methoxyphenyl)-1,6-dimethyl-7-oxo-4,5,5a,6,7,9a-hexahydro-1H-benzo[g]indazole-8-carbonitrile;

rac-(5aS,6S,9aR)-6-methyl-7-oxo-3,9a-diphenyl-4,5,5a,6,7,9a-hexahydro-1H-benzo[g]indazole-8-carbonitrile;

(7S)-7-methyl-8-oxo-2,10a-diphenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(7S)-4-methoxy-7-methyl-8-oxo-2,10a-diphenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(7S,10aS)-2-anilino-7-methyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-4-methoxy-2-(2-methoxyphenyl)-7-methyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-7-methyl-8-oxo-10a-phenyl-2-(pyridin-3-yl)-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-2-(ethylamino)-7-methyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-4-methoxy-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-2-anilino-4-methoxy-7-methyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-2-[(4-bromophenyl)amino]-4-methoxy-7-methyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-2-anilino-7-methyl-8-oxo-10a-phenyl-4-(pyrimidin-5-yl)-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-2,7-dimethyl-4-(1-methyl-1H-imidazol-5-yl)-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-2,7-dimethyl-4-(2-methyl-1,3-thiazol-5-yl)-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-7-methyl-2-(morpholin-4-yl)-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-4-hydroxy-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-2,7-dimethyl-8-oxo-4,10a-diphenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-2,7-dimethyl-8-oxo-10a-phenyl-4-(pyrimidin-5-yl)-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-4-(3-furyl)-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6S,9aR)-6-methyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

(6aS,7S,10aR)-2-(2-fluorophenyl)-4-methoxy-7-methyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(5aS,6S,9aR)-1,6-dimethyl-7-oxo-9a-phenyl-3-(pyridin-3-yl)-4,5,5a,6,7,9a-hexahydro-1H-benzo[g]indazole-8-carbonitrile;

(6aS,7S,10aR)-2,7-dimethyl-8-oxo-10a-phenyl-4-(pyridin-4-yl)-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6S,9aR)-2-acetyl-6-methyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

(6aS,7S,10aR)-7-methyl-8-oxo-10a-phenyl-2-(pyridin-4-yl)-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-2-(diethylamino)-7-methyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-2-(2-fluorophenyl)-4-isopropoxy-7-methyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

methyl (6S,9aR)-8-cyano-6-methyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-2-carboxylate;

rac-(6aS,7S,10aR)-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-2,7-dimethyl-8-oxo-10a-phenyl-4-(1H-pyrazol-4-yl)-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-2,7-dimethyl-4-(1-methyl-1H-pyrazol-4-yl)-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6S,9aR)-6-methyl-2-(methylsulfonyl)-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

phenyl (6S,9aR)-8-cyano-6-methyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-2-carboxylate;

(6S,9aR)-2-benzoyl-6-methyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

tert-butyl {2-[(6S,9aR)-8-cyano-6-methyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazol-2-yl]-2-oxoethyl}carbamate;

(6S,9aR)-6-methyl-7-oxo-9a-phenyl-2-(1,3-thiazol-4-ylcarbonyl)-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

(6S,9aR)-6-methyl-7-oxo-9a-phenyl-2-(phenylsulfonyl)-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

(6S,9aR)-2-glycoloyl-6-methyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

(6aS,7S,10aR)-4-(3-methoxyphenyl)-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7, 8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-2,7-dimethyl-4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-2,7-dimethyl-8-oxo-10a-phenyl-4-(quinolin-6-yl)-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

2-{3-[(6aS,7S,10aR)-9-cyano-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7,8, 0a-hexahydrobenzo[h]quinazolin-4-yl]phenyl}ethyl acetate;

(6aS,7S,10aR)-4-[3-(2-hydroxyethyl)phenyl]-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6S,9aR)-8-cyano-6-methyl-7-oxo-9a-phenyl-N-(pyridin-3-yl)-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-2-carboxamide;

(6aS,7S,10aR)-7-methyl-8-oxo-10a-phenyl-2-(pyrimidin-5-yl)-5,6,6a,7, 8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-10a-(4-fluorophenyl)-7-methyl-8-oxo-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-10a-(4-fluorophenyl)-7-methyl-8-oxo-2-(pyridin-3-yl)-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6S,9aR)-2,6-dimethyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

(5 aS,6S,9aR)-9a-(3-fluorophenyl)-6-methyl-7-oxo-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

(5 aS,6S,9aR)-9a-(4-fluorophenyl)-6-methyl-7-oxo-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

(6aS,7S,10aR)-10a-(3-fluorophenyl)-7-methyl-8-oxo-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(5aS,6S,9aR)-2-benzyl-6-methyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

(5aS,6S,9aR)-1-benzyl-6-methyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-1H-benzo[g]indazole-8-carbonitrile;

(5aS,6S,9aR)-9a-(4-methoxyphenyl)-6-methyl-7-oxo-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

methyl 3-[(6aS,7S,10aR)-9-cyano-7-methyl-8-oxo-6,6a,7,8-tetrahydrobenzo[h]quinazolin-10a(5H)-yl]benzoate;

3-[(6aS,7S,10aR)-9-cyano-7-methyl-8-oxo-6,6a,7,8-tetrahydrobenzo[h]quinazolin-10a(5H)-yl]benzoic acid;

3-[(6aS,7S,10aR)-9-cyano-7-methyl-8-oxo-6,6a,7,8-tetrahydrobenzo[h]quinazolin-10a(5H)-yl]benzamide;

methyl 3-[(5aS,6S,9aR)-8-cyano-6-methyl-7-oxo-2,4,5,5a,6,7-hexahydro-9aH-benzo[g]indazol-9a-yl]benzoate;

methyl 4-[(5aS,6S,9aR)-8-cyano-6-methyl-7-oxo-2,4,5,5a,6,7-hexahydro-9aH-benzo[g]indazol-9a-yl]benzoate;

methyl 4-[(6aS,7S,10aR)-9-cyano-7-methyl-8-oxo-6,6a,7,8-tetrahydrobenzo[h]quinazolin-10a(5H)-yl]benzoate;

(5aS,6S,9aR)-1-(4-bromobenzyl)-6-methyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-1H-benzo[g]indazole-8-carbonitrile;

4-[(6aS,7S,10aR)-9-cyano-7-methyl-8-oxo-6,6a,7,8-tetrahydrobenzo[h]quinazolin-10a(5H)-yl]benzoic acid;

(6aS,7S,10aR)-10a-(4-methoxyphenyl)-2,7-dimethyl-8-oxo-4-(pyrimidin-5-yl)-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-10a-(4-fluorophenyl)-2,7-dimethyl-8-oxo-4-(pyrimidin-5-yl)-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-10a-(3-fluorophenyl)-2,7-dimethyl-8-oxo-4-(pyrimidin-5-yl)-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-10a-(4-methoxyphenyl)-7-methyl-8-oxo-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

3-[(5aS,6S,9aR)-8-cyano-6-methyl-7-oxo-2,4,5,5a,6,7-hexahydro-9aH-benzo[g]indazol-9a-yl]benzoic acid;

(6S,9aR)-9a-(4-hydroxyphenyl)-6-methyl-7-oxo-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

(6aS,7S,10aR)-7-methyl-8-oxo-10a-[4-(pyrrolidin-1-ylcarbonyl)phenyl]-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-2-(2,6-difluorophenyl)-7-methyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

methyl 4-[(6aS,7S,10aR)-9-cyano-7-methyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazolin-2-yl]benzoate;

(6aS,7S,10aR)-4-(1-acetyl-1H-pyrazol-4-yl)-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

4-[(6aS,7S,10aR)-9-cyano-7-methyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazolin-2-yl]benzoic acid;

(6S,9aR)-9a-(3-fluorophenyl)-3-[3-(3-hydroxypropyl)phenyl]-6-methyl-7-oxo-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

(6aS,7S,10aR)-4-[4-(4-bromo-1H-pyrazol-5-yl)phenyl]-10a-(4-methoxyphenyl)-2,7-dimethyl-8-oxo-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-10a-(4-methoxyphenyl)-2,7-dimethyl-8-oxo-4-[4-(1H-pyrazol-5-yl)phenyl]-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-4-[4-(4-bromo-1H-pyrazol-5-yl)phenyl]-10a-(4-fluorophenyl)-2,7-dimethyl-8-oxo-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(5aS,6S,9aR)-9a-(4-fluorophenyl)-2-glycyl-6-methyl-7-oxo-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

(6aS,7S,10aR)-10a-(4-fluorophenyl)-2,7-dimethyl-8-oxo-4-[4-(1H-pyrazol-5-yl)phenyl]-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-7-methyl-8-oxo-10a-phenyl-2-(pyrazin-2-yl)-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-2-tert-butyl-7-methyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6S,9aR)-6-methyl-7-oxo-9a-phenyl-3-(pyridin-3-yl)-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

(6S,9aR)-6-methyl-7-oxo-9a-phenyl-3-(pyrimidin-5-yl)-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

(6S,9aR)-3-(3-hydroxyphenyl)-6-methyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

(6S,9aR)-6-methyl-3-(1-methyl-1H-pyrazol-4-yl)-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

(6aS,7S,10aR)-4-(1H-benzimidazol-5-yl)-10a-(4-methoxyphenyl)-2,7-dimethyl-8-oxo-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-4-(1H-benzimidazol-5-yl)-10a-(4-fluorophenyl)-2,7-dimethyl-8-oxo-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-4-(3-bromo-1H-indazol-7-yl)-10a-(4-fluorophenyl)-2,7-dimethyl-8-oxo-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-10a-(4-fluorophenyl)-4-(1H-indazol-7-yl)-2,7-dimethyl-8-oxo-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-4-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-10a-(4-fluorophenyl)-2,7-dimethyl-8-oxo-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

3-[(6aS,7S,10aR)-9-cyano-7-methyl-8-oxo-6,6a,7,8-tetrahydrobenzo[h]quinazolin-10a(5H)-yl]-N-phenylbenzamide;

3-[(6aS,7S,10aR)-9-cyano-7-methyl-8-oxo-6,6a,7,8-tetrahydrobenzo[h]quinazolin-10a(5H)-yl]-N-propylbenzamide;

(5aS,6S,9aR)-2,6-dimethyl-7-oxo-9a-phenyl-3-(pyridazin-4-yl)-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

methyl 4-[(6aS,7S,10aR)-9-cyano-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazolin-4-yl]-1H-pyrazole-1-carboxylate;

methyl 3-[(6aS,7S,10aR)-9-cyano-7-methyl-8-oxo-2-phenyl-6,6a,7,8-tetrahydrobenzo[h]quinazolin-10a(5H)-yl]benzoate;

3-[(6aS,7S,10aR)-9-cyano-7-methyl-8-oxo-2-phenyl-6,6a,7,8-tetrahydrobenzo[h]quinazolin-10a(5H)-yl]benzoic acid;

methyl 3-[(6aS,7S,10aR)-9-cyano-2-[4-(methoxycarbonyl)phenyl]-7-methyl-8-oxo-6,6a,7,8-tetrahydrobenzo[h]quinazolin-10a(5H)-yl]benzoate;

(6aS,7S,10aR)-2-chloro-4-methoxy-7-methyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-2,4-dimethoxy-7-methyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

3-[(6aS,7S,10aR)-2-(4-carboxyphenyl)-9-cyano-7-methyl-8-oxo-6,6a,7,8-tetrahydrobenzo[h]quinazolin-10a(5H)-yl]benzoic acid;

(3R,3aR,5aS,6S,9aR)-2,6-dimethyl-7-oxo-3,9a-diphenyl-3,3a,4,5,5a,6,7,9a-octahydro-2H-benzo[g]indazole-8-carbonitrile;

(6S,9aR)-3-(6-aminopyridin-3-yl)-6-methyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

(6aS,7S,10aR)-4-(imidazo[1,2-a]pyridin-6-yl)-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-4-(4-hydroxyphenyl)-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-4-(3-hydroxyphenyl)-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-4-[3-(3-hydroxypropyl)phenyl]-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-2-(5-bromo-2-hydroxyphenyl)-7-methyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

N-{4-[(6S,9aR)-8-cyano-6-methyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazol-3-yl]phenyl}methanesulfonamide;

N-{3-[(6S,9aR)-8-cyano-6-methyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazol-3-yl]phenyl}methanesulfonamide;

(6aS,7S,10aR)-2-(4-hydroxyphenyl)-7-methyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6S,9aR)-3-[4-(2-hydroxyethyl)phenyl]-6-methyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

(6S,9aR)-3-[3-(2-hydroxyethyl)phenyl]-6-methyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

(6S,9aR)-3-[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]-6-methyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

(6aS,7S,10aR)-4-(4′-aminobiphenyl-3-yl)-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-4-(4′-hydroxybiphenyl-3-yl)-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-10a-[4-(benzyloxy)phenyl]-7-methyl-8-oxo-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-10a-(4-hydroxyphenyl)-7-methyl-8-oxo-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-2,7-dimethyl-8-oxo-10a-phenyl-4-[4-(pyridin-4-yl)phenyl]-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6S,9aR)-3-[3-(3-hydroxypropyl)phenyl]-6-methyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

N-{3′-[(6aS,7S,10aR)-9-cyano-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazolin-4-yl]biphenyl-3-yl}methanesulfonamide;

3-{3-[(6aS,7S,10aR)-9-cyano-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazolin-4-yl]phenyl}propyl acetate;

(6S,9aR)-3-[5-(hydroxymethyl)pyridin-3-yl]-6-methyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

(6aS,7S,10aR)-4-[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-10a-[3-(benzyloxy)phenyl]-7-methyl-8-oxo-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-2,7-dimethyl-8-oxo-10a-phenyl-4-[4-(pyrimidin-5-yl)phenyl]-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-2,7-dimethyl-8-oxo-10a-phenyl-4-(pyrimidin-5-yl)-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carboxamide;

(6aS,7S,10aR)-7-methyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carboxamide;

(6aS,7S,10aR)-4-(5-bromo-6-hydroxypyridin-3-yl)-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-4-(6-hydroxypyridin-3-yl)-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

methyl 3′-[(6aS,7S,10aR)-9-cyano-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazolin-4-yl]biphenyl-4-carboxylate;

3′-[(6aS,7S,10aR)-9-cyano-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazolin-4-yl]biphenyl-4-carboxamide;

4-[(6aS,7S,10aR)-9-cyano-7-methyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazolin-2-yl]benzamide;

(6aS,7S,10aR)-10a-(3-hydroxyphenyl)-7-methyl-8-oxo-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

4-[(6aS,7S,10aR)-9-cyano-7-methyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazolin-2-yl]-N,N-dimethylbenzamide;

(6aS,7S,10aR)-2,7-dimethyl-4-[4-(1-methyl-1H-imidazol-5-yl)phenyl]-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(5aS,6S,9aR)-6-methyl-7-oxo-9a-phenyl-3-(pyridazin-4-yl)-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

{4-[(6S,9aR)-8-cyano-6-methyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazol-3-yl]-1H-pyrazol-1-yl}acetic acid;

methyl 3-[(6aS,7S,10aR)-9-carbamoyl-7-methyl-8-oxo-6,6a,7,8-tetrahydrobenzo[h]quinazolin-10a(5H)-yl]benzoate;

(5aS,6S,9aR)-2,6-dimethyl-7-oxo-9a-phenyl-3-[4-(pyridin-4-yl)phenyl]-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

(5aS,6S,9aR)-2,6-dimethyl-7-oxo-9a-phenyl-3-[4-(pyrimidin-5-yl)phenyl]-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

(6aS,7S,10aR)-2,7-dimethyl-8-oxo-10a-phenyl-4-[4-(pyrimidin-5-yl)phenyl]-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carboxamide;

(6aS,7S,10aR)-4-[3-bromo-4-(morpholin-4-yl)phenyl]-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-2,7-dimethyl-8-oxo-10a-phenyl-4-(pyridin-3-ylamino)-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(5aS,6S,9aR)-3-(3-bromophenyl)-2,6-dimethyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

(5aS,6S,9aR)-3-(4′-aminobiphenyl-3-yl)-2,6-dimethyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

N-{3′-[(5aS,6S,9aR)-8-cyano-2,6-dimethyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazol-3-yl]biphenyl-3-yl}methanesulfonamide;

(5aS,6S,9aR)-2,6-dimethyl-7-oxo-9a-phenyl-3-[3-(pyridazin-4-yl)phenyl]-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

N-{3′-[(5aS,6S,9aR)-8-cyano-2,6-dimethyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazol-3-yl]biphenyl-4-yl}-N-(methylsulfonyl)methanesulfonamide;

(5aS,6S,9aR)-3-[3-(2-methoxypyrimidin-5-yl)phenyl]-2,6-dimethyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

methyl 3-{3-[(6aS,7S,10aR)-9-cyano-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazolin-4-yl]phenyl}propanoate;

3-{3-[(6aS,7S,10aR)-9-cyano-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazolin-4-yl]phenyl}propanoic acid;

3-{3-[(6aS,7S,10aR)-9-cyano-2,7-dimethyl-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazolin-4-yl]phenyl}propanamide;

(5aS,6S,9aR)-3-[1-(4-cyanophenyl)-1H-pyrazol-4-yl]-6-methyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

(5aS,6S,9aR)-6-methyl-7-oxo-9a-phenyl-3-[1-(pyridin-3-yl)-1H-pyrazol-4-yl]-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

(5aS,6S,9aR)-6-methyl-7-oxo-9a-phenyl-3-[1-(pyridin-4-yl)-1H-pyrazol-4-yl]-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

rac-(5aS,6S,9aR)-2,6-dimethyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

rac-(5aS,6S,9aR)-1,6-dimethyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-1H-benzo[g]indazole-8-carbonitrile;

rac-(5aS,6S,9aR)-9a-benzyl-2,6-dimethyl-7-oxo-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

rac-(5aS,6S,9aR)-9a-benzyl-1,6-dimethyl-7-oxo-4,5,5a,6,7,9a-hexahydro-1H-benzo[g]indazole-8-carbonitrile;

rac-(5aS,6S,9aR)-9a-benzyl-2,6-dimethyl-7-oxo-3-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

rac-(5aS,6S,9aR)-9a-benzyl-2,6-dimethyl-7-oxo-3-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carboxamide;

3′-[(5aS,6S,9aR)-8-cyano-2,6-dimethyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazol-3-yl]biphenyl-3-carboxylic acid;

(5aS,6S,9aR)-2,6-dimethyl-7-oxo-9a-phenyl-3-[3-(1H-pyrazol-4-yl)phenyl]-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

N-({3′-[(5aS,6S,9aR)-8-cyano-2,6-dimethyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazol-3-yl]biphenyl-4-yl}methyl)methanesulfonamide;

N-{3′-[(5aS,6S,9aR)-8-cyano-2,6-dimethyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazol-3-yl]biphenyl-4-yl}methanesulfonamide;

(5aS,6S,9aR)-3-(4′-hydroxybiphenyl-3-yl)-2,6-dimethyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

3′-[(5aS,6S,9aR)-8-cyano-2,6-dimethyl-7-oxo-9a-phenyl-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazol-3-yl]biphenyl-4-carboxamide;

(6aS,7S,10aR)-2,7-dimethyl-8-oxo-10a-phenyl-4-(pyridazin-4-yl)-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-7-methyl-2-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]-8-oxo-10a-phenyl-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

(6aS,7S,10aR)-10a-(4-methoxyphenyl)-2,7-dimethyl-4-(1-methyl-1H-imidazol-5-yl)-8-oxo-5,6,6a,7,8,10a-hexahydrobenzo[h]quinazoline-9-carbonitrile;

methyl 4-[(6aS,7S,10aR)-9-cyano-2,7-dimethyl-4-(1-methyl-1H-imidazol-5-yl)-8-oxo-6,6a,7,8-tetrahydrobenzo[h]quinazolin-10a(5H)-yl]benzoate;

methyl 4-[(6aS,7S,10aR)-4-(4-bromo-1-methyl-1H-imidazol-5-yl)-9-cyano-2,7-dimethyl-8-oxo-6,6a,7,8-tetrahydrobenzo[h]quinazolin-10a(5H)-yl]benzoate;

(5aS,6S,9aR)-2,6-dimethyl-7-oxo-9a-phenyl-3-(pyrimidin-5-yl)-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile;

(5aS,6S,9aR)-2,6-dimethyl-7-oxo-9a-phenyl-3-(pyridin-3-yl)-4,5,5a,6,7,9a-hexahydro-2H-benzo[g]indazole-8-carbonitrile; and

(5aS,6S,9aR)-1,6-dimethyl-7-oxo-9a-phenyl-3-(pyrimidin-5-yl)-4,5,5a,6,7,9a-hexahydro-1H-benzo[g]indazole-8-carbonitrile.

23. The compound, or a salt thereof, of claim 1 , wherein the salt is a pharmaceutically acceptable salt.

24. A pharmaceutical composition comprising a therapeutically effective amount of claim 1 , or a pharmaceutically acceptable salt thereof, in combination with a pharmaceutically acceptable carrier.

Assignments (11)
RELEASE OF SECURITY INTEREST Recorded Apr 9, 2025
From: BIOPHARMA CREDIT PLC
To: REATA PHARMACEUTICALS HOLDINGS, LLC; REATA PHARMACEUTICALS GLOBAL, INC.; REATA PHARMACEUTICALS, INC.
Reel/Frame 070793/0228 →
RELEASE OF SECURITY INTEREST Recorded Apr 9, 2025
From: BIOPHARMA CREDIT PLC
To: REATA PHARMACEUTICALS HOLDINGS, LLC; REATA PHARMACEUTICALS GLOBAL, INC.; REATA PHARMACEUTICALS, INC.
Reel/Frame 070793/0130 →
AMENDED AND RESTATED PATENT SECURITY AGREEMENT Recorded Jul 12, 2023
From: REATA PHARMACEUTICALS HOLDINGS, LLC; REATA PHARMACEUTICALS GLOBAL, INC.; REATA PHARMACEUTICALS, INC.
To: BIOPHARMA CREDIT PLC
Reel/Frame 064264/0557 →
PATENT SECURITY AGREEMENT Recorded May 18, 2023
From: REATA PHARMACEUTICALS HOLDINGS, LLC; REATA PHARMACEUTICALS GLOBAL, INC.; REATA PHARMACEUTICALS, INC.
To: BIOPHARMA CREDIT PLC
Reel/Frame 063697/0461 →
RELEASE OF SECURITY INTEREST Recorded Jun 24, 2020
From: OXFORD FINANCE LLC, AS COLLATERAL AGENT
To: REATA PHARMACEUTICALS, INC.
Reel/Frame 053034/0018 →
SECURITY INTEREST Recorded Jun 14, 2018
From: REATA PHARMACEUTICALS, INC.
To: OXFORD FINANCE LLC, AS COLLATERAL AGENT
Reel/Frame 046357/0605 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 7, 2017
From: ABBVIE INC.
To: REATA PHARMACEUTICALS, INC.
Reel/Frame 041195/0768 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 16, 2016
From: AAPHARMASYN LLC
To: REATA PHARMACEUTICALS, INC.
Reel/Frame 039452/0862 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 16, 2016
From: DONNER, PAMELA; WAGNER, ROLF; SHANLEY, JASON; HEYMAN, HOWARD; KRUEGER, ALLAN; CHEN, HUI-JU; ROZEMA, MICHAEL; GRAMPOVNIK, DAVID
To: ABBVIE INC.
Reel/Frame 039452/0787 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 16, 2016
From: VISNICK, MELEAN; ANDERSON, ERIC; JIANG, XIN; BENDER, CHRISTOPHER F.
To: REATA PHARMACEUTICALS, INC.
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ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 16, 2016
From: BOLTON, GARY LOUIS; CAPRATHE, BRADLEY WILLIAM; LEE, CHITASE; ROARK, WILLIAM HOWARD
To: AAPHARMASYN LLC
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Continuity (2)
Provisional Application 61931291 · Jan 24, 2014
Related Publication 20150225397A1 · Aug 13, 2015