IP Library › Granted Patent US 9,090,561

Granted Patent B2

US 9,090,561 · App. 13/614,838 · Granted Jul 28, 2015

Acetylenic heteroaryl compounds

Inventors: Yihan Wang (Newton, MA); Xiaotian Zhu (Newton, MA); Rajeswari Sundaramoorthi (Watertown, MA); Wei-Sheng Huang (Acton, MA); Dong Zou (Concord, MA); R. Mathew Thomas (Sharon, MA); Jiwei Qi (West Roxbury, MA); Jan Antoinette C. Romero (Somerville, MA); David C. Dalgarno (Brookline, MA); William C. Shakespeare (Southborough, MA); Tomi K. Sawyer (Southborough, MA); Chester A. Metcalf, III (Needham, MA)

Assignee: ARIAD Pharmaceuticals, Inc.

C07D213/56 C07D213/73 C07D213/75 C07D213/78 C07D217/14 C07D217/22 C07D237/20 C07D237/28 C07D239/26 C07D241/12 C07D241/20 C07D401/12 C07D401/14 C07D403/12 C07D405/06 C07D413/12 C07D417/12 C07D471/04

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Quick Facts

Patent No.: US 9,090,561
App. No.: 13/614,838
Granted: Jul 28, 2015
Kind: B2

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Abstract

This invention relates to compounds of the general formula: in which the variable groups are as defined herein, and to their preparation and use.

Claims (127)

1. A compound of Formula I, a tautomer thereof, or a pharmaceutically acceptable salt thereof:

wherein:

Ring T represents a substituted or unsubstituted 6-membered heteroaryl ring, where the heteroaryl comprises 1 N;

Ring A represents a 5- or 6-membered aryl or heteroaryl ring, where the heteroaryl comprises 1-4 heteroatoms selected from N, O, and S;

Ring B represents a 5- or 6-membered aryl or heteroaryl, where the heteroaryl comprises 1-4 heteroatoms selected from N, O, and S;

L 1 is C(O)NR 1 ;

at each occurrence, R a and R b are independently selected from the group consisting of halo, —CN, —NO 2 , —R 4 , —OR 2 , —NR 2 R 3 , —C(O)YR 2 , —OC(O)YR 2 , —NR 2 C(O)YR 2 , —SC(O)YR 2 , —NR 2 C(═S)YR 2 , —OC(═S)YR 2 , —C(═S)YR 2 , —YC(═NR 3 )YR 2 , —YP(═O)(YR 4 )(YR 4 ), —Si(R 4 ) 3 , —NR 2 SO 2 R 2 , —S(O) r R 2 , —SO 2 NR 2 R 3 and —NR 2 SO 2 NR 2 R 3 , wherein Y is independently a bond, —O—, —S— or —NR 3 —;

R 1 , R 2 and R 3 are independently selected from H, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, C 6-14 aryl, C 5-14 heterocyclyl where the heterocyclyl comprises 1-4 heteroatoms selected from N, O, and S, and C 5-14 heteroaryl, where the heteroaryl comprises 1-4 heteroatoms selected from N, O, and S;

wherein the NR 2 R 3 moiety is optionally a 5- or 6-membered saturated, partially saturated or unsaturated ring, which is optionally substituted and which contains 0-2 additional heteroatoms selected from N, O and S(O) r ;

each occurrence of R 4 is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, C 6-14 aryl, C 5-14 heterocyclyl where the heterocyclyl comprises 1-4 heteroatoms selected from N, O, and S, and C 5-14 heteroaryl, where the heteroaryl comprises 1-4 heteroatoms selected from N, O, and S;

(a) X 1 is CH or CR t1 wherein R t1 is halo, OR 5 , alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, C 6-14 aryl, carbon linked C 5-14 heteroaryl where the heteroaryl comprises 1-4 heteroatoms selected from N, O, and S, or carbon linked C 5-14 heterocyclyl where the heterocyclyl comprises 1-4 heteroatoms selected from N, O, and S; wherein R 5 is H, alkyl, alkenyl, or alkynyl; and

X 2 is CR t2 and X 3 is CR t3 wherein R t2 and R t3 are independently selected from H or R a , with the proviso that when X 1 is CH and R t3 is H, R t2 is not —C(O)OCH 3 , —C(O)OH or H; and where if X 1 is CH, then at least one of R t2 and R t3 is R a ;

alternatively, R t2 and R t3 can form together with the atoms to which they are attached, a saturated, partially saturated or unsaturated 5- or 6-membered ring, comprising carbon atoms and 0-3 heteroatoms selected from O, N, S(O) r and C(O) and the said ring is optionally substituted; with the proviso that when X 1 is CH, R t2 and R t3 do not form an unsubstituted phenyl;

or,

(c) X 1 is CR t , X 2 is CR t2 and X 3 is CR t3 , wherein R t is selected from —CN, —NO 2 , —OR 6 , —NR 2 R 3 , —C(O)YR 2 , —OC(O)YR 2 , —NR 2 C(O)YR 2 , —SC(O)YR 2 , —NR 2 C(═S)YR 2 , —OC(═S)YR 2 , —C(═S)YR 2 , —YC(═NR 3 )YR 2 , —YP(═O)(YR 4 )(YR 4 ), —Si(R 4 ) 3 , —NR 2 SO 2 R 2 , —S(O) r R 2 , —SO 2 NR 2 R 3 and —NR 2 SO 2 NR 2 R 3 , wherein R 6 is cycloalkyl, cycloalkenyl, cycloalkynyl, C 6-14 aryl, C 5-14 heteroaryl, where the heteroaryl comprises 1-4 heteroatoms selected from N, O, and S, or C 5-14 heterocyclyl where the heterocyclyl comprises 1-4 heteroatoms selected from N, O, and S, and;

(c)-1: at least one of R t , R t2 , R t3 , R a and R b is or contains a YP(═O)(YR 4 )(YR 4 ), a Si(R 4 ) 3 or —YC(═NR 3 )YR 2 substituent; or

(c)-2: at least one of R a and R t is or contains a —NR 2 C(═S)OR 2 , —OC(═S)YR 2 , or —C(═S)OR 2 substituent; or

(c)-3: at least one of R b , R t2 and R t3 is or contains a —NR 2 C(═S)YR 2 , —OC(═S)YR 2 , or —C(═S)YR 2 substituent; or

(c)-4: R t2 and R t3 form together with the atoms to which they are attached, a saturated, partially saturated or unsaturated 5- or 6-membered ring, comprising carbon atoms and 0-3 heteroatoms selected from O, N, S(O) r and C(O), wherein the ring is optionally substituted; and,

alternatively R t and R t2 can form together with the atoms to which they are attached, a saturated, partially saturated or unsaturated 5- or 6-membered ring, comprising carbon atoms and 0-3 heteroatoms selected from O, N, S(O) r and C(O), the ring being optionally substituted;

each of the foregoing alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, C 6-14 aryl, C 5-14 heteroaryl, where the heteroaryl comprises 1-4 heteroatoms selected from N, O, and S, or C 5-14 heterocyclyl, where the heterocyclyl comprises 1-4 heteroatoms selected from N, O, and S, moieties are optionally substituted;

each optional substituent on an unsaturated carbon atom of a C 6-14 aryl or C 5-14 heteroaryl group, where the heteroaryl comprises 1-4 heteroatoms selected from N, O, and S, is a halo, alkyl, alkenyl, alkynyl, —CN, —R 4 , —OR 2 , —S(O) r R 2 , —SO 2 NR 2 R 3 , NR 2 R 3 , —(CO)YR 2 , —O(CO)YR 2 , —NR 2 (CO)YR 2 , —S(CO)YR 2 , —NR 2 C(═S)YR 2 , —OC(═S)YR 2 , —C(═S)YR 2 , —YC(═NR 3 )Y′R 2 , —COCOR 2 , —COMCOR 2 , —YP(═O)(YR 4 )(YR 4 ), —Si(R 4 ) 3 , —NO 2 , —NR 2 SO 2 R 2 or —NR 2 SO 2 NR 2 R 3 moiety;

each M is a 1-6 carbon alkyl group;

each optional substituent on an alkyl, alkenyl, alkynyl, alkoxy, haloalkyl, cycloalkyl, cycloalkenyl, cycloalkynyl or non-aromatic C 5-14 heterocyclic moiety, where the heterocyclic comprises 1-4 heteroatoms selected from N, O, and S, is independently a halo, alkyl, alkenyl, alkynyl, —CN, —R 4 , —OR 2 , —S(O) r R 2 , —SO 2 NR 2 R 3 , —NR 2 R 3 , —(CO)YR 2 , —O(CO)YR 2 , —NR 2 (CO)YR 2 , —S(CO)YR 2 , —NR 2 C(═S)YR 2 , —OC(═S)YR 2 , —C(═S)YR 2 , —YC(═NR 3 )Y′R 2 , —COCOR 2 , —COMCOR 2 , —YP(═O)(YR 4 )(YR 4 ), —Si(R 4 ) 3 , —NO 2 , —NR 2 SO 2 R 2 or —NR 2 SO 2 NR 2 R 3 moiety;

each optional substituent on a nitrogen is R 4 , —NR 2 R 3 , —C(═O)R 2 , —C(═O)OR 2 , —C(═O)SR 2 , —C(═O)NR 2 R 3 , —C(═NR 2 )NR 2 R 3 , —C(═NR 2 )OR 2 , —C(═NR 2 )R 3 , —COCOR 2 , —COMCOR 2 , —CN, —SO2R 3 , —S(O)R 3 , —P(═O)(YR 2 )(YR 2 ), —NR 2 SO2R 3 or —NR 2 SO2NR 2 R 3 ;

m is 0, 1, 2, 3 or 4;

p is 0, 1, 2, 3, 4 or 5; and

r is 0, 1 or 2.

2. The compound of Formula I, a tautomer thereof, or a pharmaceutically acceptable salt thereof:

wherein:

Ring T represents a substituted or unsubstituted 6-membered heteroaryl ring, comprising 1 nitrogen;

Ring A represents a 5- or 6-membered aryl or heteroaryl ring, where the heteroaryl comprises 1-4 heteroatoms selected from N, O, and S;

Ring B represents a 5- or 6-membered aryl or heteroaryl, where the heteroaryl comprises 1-4 heteroatoms selected from N, O, and S;

L 1 is C(O)NR 1 ;

X 2 is CR t2 and X 3 is CR t3 wherein R t2 and R t3 are independently selected from H or R a ; where if X 1 is CH, then at least one of R t2 and R t3 is R a ; and

alternatively R t2 and R t3 can form together with the atoms to which they are attached, a saturated, partially saturated or unsaturated 5- or 6-membered ring, comprising carbon atoms and 0-3 heteroatoms selected from O, N, S(O) r and C(O), and the said ring is optionally substituted, with the proviso that when X 1 is CH, R t2 and R t3 do not form an unsubstituted phenyl;

or,

(c)-1: at least one of R t , R t2 , R t3 , R a and R b is or contains a YP(═O)(YR 4 )(YR 4 ), a Si(R 4 ) 3 or —YC(═NR 3 )YR 2 substituent; or

(c)-2: at least one of R a and R t is or contains a —NR 2 C(═S)OR 2 , —OC(═S)YR 2 , or —C(═S)OR 2 substituent; or

(c)-3: at least one of R b , R t2 and R t3 is or contains a —NR 2 C(═S)YR 2 , —OC(═S)YR 2 , or —C(═S)YR 2 substituent; or

each of the foregoing alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, C 6-14 aryl, C 5-14 heteroaryl, where the heteroaryl comprises 1-4 heteroatoms selected from N, O, and S, or C 5-14 heterocyclyl where the heterocyclyl comprises 1-4 heteroatoms selected from N, O, and S moieties are optionally substituted;

each optional substituent on an unsaturated carbon atom of a C 6-14 aryl or C 5-14 heteroaryl group, where the heteroaryl comprises 1-4 heteroatoms selected from N, O, and S, is a halo, alkyl, alkenyl, alkynyl, —CN, —R 4 , —OR 2 , —S(O) r R 2 , —SO 2 NR 2 R 3 , —NR 2 R 3 , —(CO)YR 2 , —O(CO)YR 2 , —NR 2 (CO)YR 2 , —S(CO)YR 2 , —NR 2 C(═S)YR 2 , —OC(═S)YR 2 , —C(═S)YR 2 , —YC(═NR 3 )Y′R 2 , —COCOR 2 , —COMCOR 2 , —YP(═O)(YR 4 )(YR 4 ), —Si(R 4 ) 3 , —NO 2 , —NR 2 SO 2 R 2 or —NR 2 SO 2 NR 2 R 3 moiety;

each M is a 1-6 carbon alkyl group;

m is 0, 1, 2, 3 or 4;

p is 0, 1, 2, 3, 4 or 5;

r is 0, 1 or 2; and

with the proviso that the compound is not:

3. The compound of claim 1 wherein:

X 1 is CH or CR t1 ;

X 2 is CR t2 ; and

X 3 is CR t3 .

4. The compound of claim 2 having the formula II:

wherein:

X 1 is CR t , CR t1 or CH;

E is a saturated, partially saturated or unsaturated 5- or 6-membered ring, comprising carbon atoms and 0-3 heteroatoms selected from O, N, S(O) r2 C(O), and C(═S) and the said ring is optionally substituted with R e ;

each occurrence of R e is independently selected from the group consisting of halo, ═O, ═S, —CN, —NO 2 , —R 4 , —OR 2 , —NR 2 R 3 , —C(O)YR 2 , —OC(O)YR 2 , —NR 2 C(O)YR 2 , —SC(O)YR 2 , —NR 2 C(═S)YR 2 , —OC(═S)YR 2 , —C(═S)YR 2 , —YC(═NR 3 )YR 2 , —YP(═O)(YR 4 )(YR 4 ), —Si(R 4 ) 3 , —NR 2 SO 2 R 2 , —S(O) r R 2 , —SO 2 NR 2 R 3 and —NR 2 SO 2 NR 2 R 3 , wherein Y is independently a bond, —O—, —S— or —NR 3 —;

R 2 and R 3 are independently selected from H, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, C 6-14 aryl, C 5-14 heterocyclyl where the heterocyclyl comprises 1-4 heteroatoms selected from N, O, and S, and C 5-14 heteroaryl, where the heteroaryl comprises 1-4 heteroatoms selected from N, O, and S;

each of the foregoing alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, C 6-14 aryl, C 5-14 heteroaryl, where the heteroaryl comprises 1-4 heteroatoms selected from N, O, and S, or C 5-14 heterocyclyl where the heterocyclyl comprises 1-4 heteroatoms selected from N, O, and S moieties are optionally substituted;

each optional substituent on an unsaturated carbon atom of a C 6-14 aryl or C 5-14 heteroaryl group, where the heteroaryl comprises 1-4 heteroatoms selected from N, O, and S, is a halo, alkyl, alkenyl, alkynyl, —CN, —R 4 , —OR 2 , —S(O) r R 2 , —SO 2 NR 2 R 3 , —NR 2 R 3 , —(CO)YR 2 , —O(CO)YR 2 , —NR 2 (CO)YR 2 , —S(CO)YR 2 , —NR 2 C(═S)YR 2 , —OC(═S)YR 2 , —C(═S)YR 2 , —YC(═NR 3 )Y′R 2 , —COCOR 2 , —COMCOR 2 , —YP(═O)(YR 4 )(YR 4 ), —Si(R 4 ) 3 , —NO 2 , —NR 2 SO 2 R 2 or —NR 2 SO 2 NR 2 R 3 moiety;

each M is a 1-6 carbon alkyl group;

each optional substituent on an alkyl, alkenyl, alkynyl, alkoxy, haloalkyl, cycloalkyl, cycloalkenyl, cycloalkynyl or non-aromatic C 5-14 heterocyclic moiety, where the heterocyclic comprises 1-4 heteroatoms selected from N, O, and S, is independently a halo, alkyl, alkenyl, alkynyl, —CN, —R 4 , —OR 2 , —S(O) r R 2 , SO 2 NR 2 R 3 , —NR 2 R 3 , —(CO)YR 2 , —O(CO)YR 2 , —NR 2 (CO)YR 2 , —S(CO)YR 2 , —NR 2 C(═S)YR 2 , —OC(═S)YR 2 , —C(═S)YR 2 , —YC(═NR 3 )Y′R 2 , —COCOR 2 , —COMCOR 2 , —YP(═O)(YR 4 )(YR 4 ), —Si(R 4 ) 3 , —NO 2 , —NR 2 SO 2 R 2 or —NR 2 SO 2 NR 2 R 3 moiety;

s is 0, 1, 2, 3 or 4; and

r is 0, 1, or 2.

5. The compound of claim 4 in which X 1 is CH.

6. The compound of claim 4 in which X 1 is CR t1 .

7. The compound of claim 1 having Formula III:

wherein:

Ring C represents a 5- or 6-membered heterocyclic or heteroaryl ring, comprising carbon atoms and 1-3 heteroatoms selected from O, N and S(O) r ;

R c , at each occurrence, is independently selected from the group consisting of halo, ═O, ═S, —CN, —NO 2 , —R 4 , —OR 2 , —NR 2 R 3 , —C(O)YR 2 , —OC(O)YR 2 , —NR 2 C(O)YR 2 , —SC(O)YR 2 , —NR 2 C(═S)YR 2 , —OC(═S)YR 2 , —C(═S)YR 2 , —YC(═NR 3 )YR 2 , —YP(═O)(YR 4 )(YR 4 ), —Si(R 4 ) 3 , —NR 2 SO 2 R 2 , —S(O) r R 2 , —SO 2 NR 2 R 3 and —NR 2 SO 2 NR 2 R 3 , wherein Y is independently a bond, —O—, —S— or —NR 3 —;

R 2 and R 3 are independently selected from H, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, C 6-14 aryl, C 5-14 heterocyclic where the heterocyclic comprises 1-4 heteroatoms selected from N, O, and S, and C 5-14 heteroaryl, where the heteroaryl comprises 1-4 heteroatoms selected from N, O, and S;

each occurrence of R 4 is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, C 6-14 aryl, C 5-14 heterocyclic where the heterocyclic comprises 1-4 heteroatoms selected from N, O, and S, and C 5-14 heteroaryl, where the heteroaryl comprises 1-4 heteroatoms selected from N, O, and S;

each of the foregoing alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, C 6-14 aryl, carbon linked C 5-14 heteroaryl where the heteroaryl comprises 1-4 heteroatoms selected from N, O, and S, or carbon linked C 5-14 heterocycle where the heterocycle comprises 1-4 heteroatoms selected from N, O, and S, moieties is optionally substituted;

each M is a 1-6 carbon alkyl group;

each optional substituent on an alkyl, alkenyl, alkynyl, alkoxy, haloalkyl, cycloalkyl, cycloalkenyl, cycloalkynyl or non-aromatic C 5-14 heterocyclic moiety, where the heterocyclic comprises 1-4 heteroatoms selected from N, O, and S, is independently a halo, alkyl, alkenyl, alkynyl, —CN, —R 4 , —OR 2 , —S(O) r R 2 , —SO 2 NR 2 R 3 , NR 2 R 3 , —(CO)YR 2 , —O(CO)YR 2 , —NR 2 (CO)YR 2 , —S(CO)YR 2 , —NR 2 C(═S)YR 2 , —OC(═S)YR 2 , —C(═S)YR 2 , —YC(═NR 3 )Y′R 2 , —COCOR 2 , —COMCOR 2 , —YP(═O)(YR 4 )(YR 4 ), —Si(R 4 ) 3 , —NO 2 , —NR 2 SO 2 R 2 or —NR 2 SO 2 NR 2 R 3 moiety;

v is 0, 1, 2, 3, 4 or 5 and

t is 0, 1, 2, 3, or 4.

8. The compound of claim 7 wherein Ring C is a substituted or unsubstituted C 5-14 heteroaryl ring, where the heteroaryl comprises 1-4 heteroatoms selected from N, O, and S.

9. The compound of claim 8 wherein Ring C is a substituted or unsubstituted imidazole ring.

10. The compound of claim 9 selected from the following formulae:

11. The compound of claim 9 having Formula II-a:

wherein X 1 is selected from CH, CR t1 , and CR t .

12. The compound of claim 11 wherein X 1 is selected from CH and CR t1 .

13. The compound of claim 1 having Formula IV:

wherein:

Ring D represents a 5- or 6-membered heterocyclic or heteroaryl ring, comprising carbon atoms and 1-3 heteroatoms independently selected from N, O, and S(O) r ;

L 2 is (CH 2 ) z , O(CH 2 ) x , NR 3 (CH 2 ) x , S(CH 2 ) x or (CH 2 ) x NR 3 C(O)(CH 2 ) x and the linkage unit can be used in either direction;

R d , at each occurrence, is selected from the group consisting of halo, ═O, ═S, —CN, —NO 2 , —R 4 , —OR 2 , —NR 2 R 3 , —C(O)YR 2 , —OC(O)YR 2 , —NR 2 C(O)YR 2 , —SC(O)YR 2 , —NR 2 C(═S)YR 2 , —OC(═S)YR 2 , —C(═S)YR 2 , —YC(═NR 3 )YR 2 , —YP(═O)(YR 4 )(YR 4 ), —Si(R 4 ) 3 , —NR 2 SO 2 R 2 , —S(O) r R 2 , —SO 2 NR 2 R 3 and —NR 2 SO 2 NR 2 R 3 , wherein Y is independently a bond, —O—, —S— or —NR 3 —;

wherein the NR 2 R 3 moiety is a 5- or 6-membered saturated, partially saturated or unsaturated ring, which is optionally substituted and which contains 0-2 additional heteroatoms selected from N, O and S(O) r ;

each of the foregoing alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, heteroaryl and heterocycle moieties is optionally substituted;

each optional substituent on an unsaturated carbon atom of a C 6-14 aryl or C 5-14 heteroaryl group, where the heteroaryl comprises 1-4 heteroatoms selected from N, O, and S, is a halo, alkyl, alkenyl, alkynyl, —CN, —R 4 , —OR 2 , —S(O) r R 2 , —SO 2 NR 2 R 3 , —NR 2 R 3 , —(CO)YR 2 , —O(CO)YR 2 , —NR 2 (CO)YR 2 , —S(CO)YR 2 , —NR 2 C(═S)YR 2 , —OC(═S)YR 2 , —C(═S)YR 2 , —YC(═NR 3 )Y′R 2 , —COCOR 2 , —COMCOR 2 , —YP(═O)(YR 4 )(YR 4 ), Si(R 4 ) 3 , —NO 2 , —NR 2 SO 2 R 2 or —NR 2 SO 2 NR 2 R 3 moiety;

each M is a 1-6 carbon alkyl group;

w is 0, 1, 2, 3, 4 or 5;

x is 0, 1, 2 or 3;

z is 1, 2, 3 or 4; and

t is 0, 1, 2, 3, or 4.

14. The compound of claim 13 wherein Ring D is a substituted or unsubstituted C 5-14 heteroaryl where the heteroaryl comprises 1-4 heteroatoms selected from N, O, and S.

15. The compound of claim 13 wherein Ring D is a substituted or unsubstituted piperazine ring and L 2 is CH 2 .

16. The compound of claim 15 having Formula IV-a:

17. The compound of claim 15 having Formula II-b:

wherein X 1 is selected from CH, CR t1 , and CR t .

18. The compound of claim 17 wherein X 1 is selected from CH and CR t1 .

19. A method for treating leukemia in a mammal in need thereof, comprising administering to the mammal a therapeutically effective amount of the compound of claim 1 ; or a pharmaceutically acceptable salt thereof.

20. A method for treating leukemia in a mammal in need thereof, comprising administering to the mammal a therapeutically effective amount of the compound of claim 7 ; or a pharmaceutically acceptable salt, thereof.

21. A method for treating leukemia in a mammal in need thereof, comprising administering to the mammal a therapeutically effective amount of the compound of claim 13 ; or a pharmaceutically acceptable salt thereof.

22. A composition comprising the compound of claim 1 ; or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier, diluent or vehicle.

23. A composition comprising the compound of claim 7 ; or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier, diluent or vehicle.

24. A composition comprising the compound of claim 13 ; or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier, diluent or vehicle.

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 29, 2015

From: WANG, YIHAN; ZHU, XIAOTIAN; SUNDARAMOORTHI, RAJESWARI; HUANG, WEI-SHENG; ZOU, DONG; THOMAS, R. MATHEW; QI, JIWEI; ROMERO, JAN ANTOINETTE C.; DALGARNO, DAVID C.; SHAKESPEARE, WILLIAM C.; SAWYER, TOMI K.; METCALF, CHESTER A., III

To: ARIAD PHARMACEUTICALS, INC.

Reel/Frame 034846/0682 →

Continuity (5)

Division 12227002

Provisional Application 60798472 · May 8, 2006

Provisional Application 60833191 · Jul 25, 2006

Provisional Application 60920688 · Mar 29, 2007

Related Publication 20130018046A1 · Jan 17, 2013