IP Library › Granted Patent US 50,643
Granted Patent E1
US 50,643 · App. 18/212,692 · Granted Oct 21, 2025

Benzamide compounds

Inventors: Joseph Robert Pinchman (San Diego, CA); Peter Qinhua Huang (San Diego, CA); Kevin Duane Bunker (Escondido, CA); Rakesh Kumar Sit (San Diego, CA); Ahmed Abdi Samatar (San Diego, CA)
Assignee: Recurium IP Holdings, LLC
A61K31/496A61K31/5355A61K45/06C07D205/04C07D207/12C07D211/46C07D211/58C07D241/04C07D295/112C07D295/13C07D413/12C07D471/04C07D519/00
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Quick Facts
Patent No.
US 50,643
App. No.
18/212,692
Granted
Oct 21, 2025
Kind
E1
Abstract

Compounds of Formula (I) are provided herein. Such compounds, as well as pharmaceutically acceptable salts and compositions thereof, are useful for treating diseases or conditions, including conditions characterized by excessive cellular proliferation, such as cancer and tumors, as well as viral infections such as HIV.

Claims (130)

1. A compound of Formula (I), or a pharmaceutically acceptable salt thereof, having the structure:

wherein:

R 1 is selected from the group consisting of hydrogen, halogen, a substituted or unsubstituted C 1 -C 6 alkyl, a substituted or unsubstituted C 1 -C 6 haloalkyl, a substituted or unsubstituted C 3 -C 6 cycloalkyl, a substituted or unsubstituted C 1 -C 6 alkoxy, an unsubstituted mono-C 1 -C 6 alkylamine and an unsubstituted di-C 1 -C 6 alkylamine;

each R 2 is independently selected from the group consisting of halogen, a substituted or unsubstituted C 1 -C 6 alkyl, a substituted or unsubstituted C 1 -C 6 haloalkyl and a substituted or unsubstituted C 3 -C 6 cycloalkyl; or

when m is 2 or 3, each R 2 is independently selected from the group consisting of halogen, a substituted or unsubstituted C 1 -C 6 alkyl, a substituted or unsubstituted C 1 -C 6 haloalkyl and a substituted or unsubstituted C 3 -C 6 cycloalkyl, or two R 2 groups taken together with the atom(s) to which they are attached form a substituted or unsubstituted C 3 -C 6 cycloalkyl or a substituted or unsubstituted 3 to 6 membered heterocyclyl;

R 3 is selected from the group consisting of X—R 3A

R 3A is a substituted or unsubstituted 5 to 10 membered heteroaryl;

R 4 is selected from the group consisting of NO 2 , S(O)R 6 , SO 2 R 6 , halogen, cyano and an unsubstituted C 1 -C 6 haloalkyl;

R 5 is selected from the group consisting of —X 1 -(Alk 1 ) n -R 7 and —X 2 (CHR 8 )-(Alk 2 ) p -X 3 —R 9 ;

Alk 1 and Alk 2 are independently selected from an unsubstituted C 1 -C 4 alkylene and a C 1 -C 4 alkylene substituted with 1, 2 or 3 substituents independently selected from fluoro, chloro, an unsubstituted C 1 -C 3 alkyl and an unsubstituted C 1 -C 3 haloalkyl;

R 6 is selected from the group consisting of a substituted or unsubstituted C 1 -C 6 alkyl, a substituted or unsubstituted C 1 -C 6 haloalkyl and a substituted or unsubstituted C 3 -C 6 cycloalkyl;

R 7 is selected from a substituted or unsubstituted C 1 -C 6 alkoxy, a substituted or unsubstituted C 3 -C 10 cycloalkyl, a substituted or unsubstituted 3 to 10 membered heterocyclyl, hydroxy, amino, a substituted or unsubstituted mono-substituted amine group, a substituted or unsubstituted di-substituted amine group, a substituted or unsubstituted N-carbamyl, a substituted or unsubstituted C-amido and a substituted or unsubstituted N-amido;

R 8 is selected from a substituted or unsubstituted 3 to 10 membered heterocyclyl(C 1 -C 6 alkyl), a substituted or unsubstituted di-C 1 -C 6 alkylamine(C 1 -C 6 alkyl) and a substituted or unsubstituted mono-C 1 -C 6 alkylamine(C 1 -C 6 alkyl);

R 9 is selected from a substituted or unsubstituted 5 to 10 membered heteroaryl and a substituted or unsubstituted C 6 -C 10 aryl;

m is 0, 1, 2 or 3;

n and p are independently selected from 0 and 1;

X 1 and X 2 are —NH—; and

X and X 3 are independently selected from the group consisting of —O—, —S— and —NH—.

2. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 1 is —CH 2 F or —CF 3 .

3. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 1 is —CHF 2 .

4. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 1 is not —CH 2 F, —CHF 2 or —CF 3 .

5. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein m is 1.

6. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein m is 2.

7. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein m is 3.

8. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein one R 2 is an unsubstituted C 1 -C 6 alkyl and any other R 2 , if present, is independently selected from the group consisting of halogen, a substituted or unsubstituted C 1 -C 6 alkyl, a substituted or unsubstituted C 1 -C 6 haloalkyl and a substituted or unsubstituted C 3 -C 6 cycloalkyl.

9. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein each R 2 is independently an unsubstituted C 1 -C 6 alkyl.

10. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein m is 2; and each R 2 is an unsubstituted methyl.

11. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein m is 0.

12. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein two R 2 groups taken together with the atom(s) to which they are attached form a substituted or unsubstituted C 3 -C 6 cycloalkyl.

13. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein two R 2 groups taken together with the atom to which they are attached form an unsubstituted cyclopropyl.

14. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein two R 2 groups taken together with the atom(s) to which they are attached form a substituted or unsubstituted 3 to 6 membered heterocyclyl.

15. The compound of claim 1 , that is also a compound of Formula (Ia), Formula (Ib), Formula (Ic) or Formula (Id):

or pharmaceutically acceptable salts of any of the foregoing.

16. The compound of claim 1 , wherein R 3 is X—R 3A .

17. The compound of claim 1 , wherein R 3A is

18. The compound of claim 1 , wherein R 3A is

19. The compound of claim 1 , wherein R 3A is a substituted 5 to 10 membered heteroaryl.

20. The compound of claim 1 , wherein X is —O—.

21. The compound of claim 1 , wherein X is —S—.

22. The compound of claim 1 , wherein X is —NH—.

23. The compound of claim 1 , wherein R 3 is

24. The compound of claim 1 , wherein R 3 is

25. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 4 is NO 2 .

26. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein R 4 is cyano.

27. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 4 is halogen.

28. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 4 is an unsubstituted C 1 -C 6 haloalkyl.

29. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 4 is —CF 3 .

30. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 4 is S(O)R 6 .

31. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 4 is SO 2 R 6 .

32. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 6 is a substituted or unsubstituted C 1 -C 6 alkyl.

33. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 6 is a substituted or unsubstituted C 3 -C 6 cycloalkyl.

34. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 6 is a substituted or unsubstituted C 1 -C 6 haloalkyl.

35. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 6 is —CF 3 .

36. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 5 is —X 1 -(Alk 1 ) n -R 7 .

37. The compound of claim 36 , or a pharmaceutically acceptable salt thereof, wherein Alk 1 is unsubstituted —(CH 2 ) 1-4 —* for which “*” represents the point of attachment to R 7 .

38. The compound of claim 36 , or a pharmaceutically acceptable salt thereof, wherein Alk 1 is selected from

39. The compound of claim 36 , or a pharmaceutically acceptable salt thereof, wherein Alk 1 is a substituted

for which “*” represents the point of attachment to R 7 .

40. The compound of claim 36 , or a pharmaceutically acceptable salt thereof, wherein Alk 1 is selected from:

41. The compound of claim 36 , or a pharmaceutically acceptable salt thereof, wherein n is 1.

42. The compound of claim 36 , or a pharmaceutically acceptable salt thereof, wherein n is 0.

43. The compound of claim 36 , or a pharmaceutically acceptable salt thereof, wherein R 7 is a substituted or unsubstituted mono-substituted amine group.

44. The compound of claim 36 , or a pharmaceutically acceptable salt thereof, wherein R 7 is a substituted or unsubstituted di-substituted amine group.

45. The compound of claim 36 , or a pharmaceutically acceptable salt thereof, wherein R 7 is selected from a substituted or unsubstituted N-carbamyl, a substituted or unsubstituted C-amido and a substituted or unsubstituted N-amido.

46. The compound of claim 36 , or a pharmaceutically acceptable salt thereof, wherein R 7 is a substituted or unsubstituted C 3 -C 10 cycloalkyl.

47. The compound of claim 36 , or a pharmaceutically acceptable salt thereof, wherein R 7 is a substituted or unsubstituted C 6 -C 10 spirocycloalkyl.

48. The compound of claim 36 , or a pharmaceutically acceptable salt thereof, wherein R 7 is a substituted or unsubstituted 3 to 10 membered heterocyclyl.

49. The compound of claim 36 , or a pharmaceutically acceptable salt thereof, wherein R 7 is a substituted or unsubstituted 6 to 10 membered spiro heterocyclyl.

50. The compound of claim 36 , or a pharmaceutically acceptable salt thereof, wherein R 7 is hydroxy or amino.

51. The compound of claim 36 , or a pharmaceutically acceptable salt thereof, wherein R 7 is unsubstituted.

52. The compound of claim 36 , or a pharmaceutically acceptable salt thereof, wherein R 7 is substituted.

53. The compound of claim 36 , or a pharmaceutically acceptable salt thereof, wherein R 7 is substituted with 1 or 2 substituents independently selected from an unsubstituted C 1 -C 6 alkyl, an unsubstituted C 1 -C 6 alkoxy, fluoro, chloro, hydroxy and —SO 2 -(unsubstituted C 1 -C 6 alkyl).

54. The compound of claim 36 , or a pharmaceutically acceptable salt thereof, wherein R 7 is selected from:

55. The compound of claim 36 , or a pharmaceutically acceptable salt thereof, wherein R 7 is selected from:

56. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 5 is —X 2 —(CHR 8 )-(Alk 2 ) p -X 3 —R 9 .

57. The compound of claim 56 , or a pharmaceutically acceptable salt thereof, wherein X 3 is —O—.

58. The compound of claim 56 , or a pharmaceutically acceptable salt thereof, wherein X 3 is —S—.

59. The compound of claim 56 , or a pharmaceutically acceptable salt thereof, wherein X 3 is —NH—.

60. The compound of claim 56 , or a pharmaceutically acceptable salt thereof, wherein Alk 2 is unsubstituted —(CH 2 ) 1-4 —* for which “*” represents the point of attachment to X 3 .

61. The compound of claim 56 , or a pharmaceutically acceptable salt thereof, wherein Alk 2 is selected from

62. The compound of claim 56 , or a pharmaceutically acceptable salt thereof, wherein Alk 2 is a substituted

for which “*” represents the point of attachment to X 3 .

63. The compound of claim 56 , or a pharmaceutically acceptable salt thereof, wherein Alk 2 is selected from:

64. The compound of claim 56 , or a pharmaceutically acceptable salt thereof, wherein p is 1.

65. The compound of claim 56 , or a pharmaceutically acceptable salt thereof, wherein p is 0.

66. The compound of claim 56 , or a pharmaceutically acceptable salt thereof, wherein R 8 is a substituted or unsubstituted 3 to 10 membered heterocyclyl(C 1 -C 6 alkyl).

67. The compound of claim 56 , or a pharmaceutically acceptable salt thereof, wherein R 8 is a substituted or unsubstituted 6 to 10 membered spiro heterocyclyl(C 1 -C 6 alkyl).

68. The compound of claim 56 , or a pharmaceutically acceptable salt thereof, wherein R 8 is a substituted or unsubstituted di-C 1 -C 6 alkylamine(C 1 -C 6 alkyl).

69. The compound of claim 56 , or a pharmaceutically acceptable salt thereof, wherein R 8 is a substituted or unsubstituted di-methylamine(C 1 -C 6 alkyl).

70. The compound of claim 56 , or a pharmaceutically acceptable salt thereof, wherein R 8 is a substituted or unsubstituted mono-C 1 -C 6 alkylamine(C 1 -C 6 alkyl).

71. The compound of claim 56 , or a pharmaceutically acceptable salt thereof, wherein R 8 is substituted.

72. The compound of claim 56 , or a pharmaceutically acceptable salt thereof, wherein R 8 is substituted with 1 or 2 substituents independently selected from an unsubstituted C 1 -C 6 alkyl, an unsubstituted C 1 -C 6 alkoxy, an unsubstituted di-C 1 -C 6 alkylamine, an unsubstituted acyl(C 1 -C 6 alkyl), an unsubstituted C-carboxy, fluoro, chloro and hydroxy.

73. The compound of claim 56 , or a pharmaceutically acceptable salt thereof, wherein R 8 is unsubstituted.

74. The compound of claim 56 , or a pharmaceutically acceptable salt thereof, wherein R 8 is selected from:

75. The compound of claim 56 , or a pharmaceutically acceptable salt thereof wherein R 8 is selected from:

76. The compound of claim 56 , or a pharmaceutically acceptable salt thereof, wherein R 9 is a substituted or unsubstituted C 6 -C 10 aryl.

77. The compound of claim 56 , or a pharmaceutically acceptable salt thereof, wherein R 9 is an unsubstituted C 6 -C 10 aryl.

78. The compound of claim 56 , or a pharmaceutically acceptable salt thereof, wherein R 9 is an unsubstituted phenyl.

79. The compound of claim 56 , or a pharmaceutically acceptable salt thereof, wherein R 9 is a substituted or unsubstituted 5 to 10 membered heteroaryl.

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

81. The compound of claim 80 , wherein the compound is selected from the group consisting of:

or a pharmaceutically acceptable salt of any of the foregoing.

82. A pharmaceutical composition comprising an effective amount of the compound of claim 1 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, diluent, excipient or combination thereof.

83. The compound of Claim 1 , or a pharmaceutically acceptable salt thereof, wherein the compound is:

84. The compound of Claim 1 , or a pharmaceutically acceptable salt thereof, wherein the compound is:

85. The compound of Claim 1 , or a pharmaceutically acceptable salt thereof, wherein the compound is:

86. The compound of Claim 1 , or a pharmaceutically acceptable salt thereof, wherein the compound is:

87. The compound of Claim 1 , or a pharmaceutically acceptable salt thereof, wherein the compound is:

88. The compound of Claim 1 , or a pharmaceutically acceptable salt thereof, wherein the compound is:

89. The compound of Claim 1 , or a pharmaceutically acceptable salt thereof, wherein the compound is:

90. The compound of Claim 1 , or a pharmaceutically acceptable salt thereof, wherein the compound is:

91. The compound of Claim 1 , or a pharmaceutically acceptable salt thereof, wherein the compound is:

92. The pharmaceutical composition of Claim 82 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

93. The pharmaceutical composition of Claim 82 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

94. The pharmaceutical composition of Claim 82 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

95. The pharmaceutical composition of Claim 82 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

96. The pharmaceutical composition of Claim 82 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

97. The pharmaceutical composition of Claim 82 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

98. The pharmaceutical composition of Claim 82 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

99. The pharmaceutical composition of Claim 82 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

100. The pharmaceutical composition of Claim 82 , wherein the compound is

or a pharmaceutically acceptable salt thereof.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 30, 2023
From: PINCHMAN, JOSEPH ROBERT; HUANG, PETER QINHUA; BUNKER, KEVIN DUANE; SIT, RAKESH KUMAR; SAMATAR, AHMED ABDI
To: ZENO MANAGEMENT, INC.
Reel/Frame 065392/0408 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 30, 2023
From: ZENO MANAGEMENT, INC.
To: ZENO ROYALTIES & MILESTONES, LLC
Reel/Frame 065392/0429 →
CHANGE OF NAME Recorded Oct 30, 2023
From: ZENO ROYALTIES & MILESTONES, LLC
To: RECURIUM IP HOLDINGS, LLC
Reel/Frame 065395/0756 →
Continuity (2)
Provisional Application 62615857 · Jan 10, 2018
Reissue 16957861 · Jan 8, 2019
References Cited (161)
US 8557983B2 · Doherty et al. · 2013 [cited by applicant]
US 8952157B2 · Ding et al. · 2015 [cited by applicant]
US 9029404B2 · Doherty et al. · 2015 [cited by applicant]
US 9034875B2 · Doherty et al. · 2015 [cited by applicant]
US 11053239B2 · Zhao et al. · 2021 [cited by applicant]
US 11344546B2 · Pinchman et al. · 2022 [cited by applicant]
US 11590126B2 · Pinchman et al. · 2023 [cited by applicant]
US 11813259B2 · Pinchman et al. · 2023 [cited by applicant]
US 11813260B1 · Pinchman et al. · 2023 [cited by applicant]
US 20060128706A1 · Bruncko et al. · 2006 [cited by applicant]
US 20060258657A1 · Bruncko et al. · 2006 [cited by applicant]
US 20070015787A1 · Bruncko et al. · 2007 [cited by applicant]
US 20070027135A1 · Bruncko et al. · 2007 [cited by applicant]
US 20080199873A1 · Anderson · 2008 [cited by examiner]
US 20100160322A1 · Bruncko et al. · 2010 [cited by applicant]
US 20100227838A1 · Shah et al. · 2010 [cited by applicant]
US 20100298323A1 · Bruncko et al. · 2010 [cited by applicant]
US 20100305122A1 · Bruncko et al. · 2010 [cited by applicant]
US 20100311751A1 · Schmitt et al. · 2010 [cited by applicant]
US 20100323020A1 · Gokhale et al. · 2010 [cited by applicant]
US 20110124628A1 · Bruncko et al. · 2011 [cited by applicant]
US 20120108590A1 · Birtalan et al. · 2012 [cited by applicant]
US 20120129853A1 · Elmore et al. · 2012 [cited by applicant]
US 20120189539A1 · Wang et al. · 2012 [cited by applicant]
US 20140199234A1 · Wang et al. · 2014 [cited by applicant]
US 20140275082A1 · Tao et al. · 2014 [cited by applicant]
US 20150336994A1 · Wang et al. · 2015 [cited by applicant]
US 20160220573A1 · Di Paolo et al. · 2016 [cited by applicant]
US 20160243247A1 · Bradner et al. · 2016 [cited by applicant]
US 20170087162A1 · Starczynowski et al. · 2017 [cited by applicant]
US 20170158666A1 · Bruncko et al. · 2017 [cited by applicant]
US 20200338071A1 · Pinchman et al. · 2020 [cited by applicant]
US 20210009543A1 · Pinchman et al. · 2021 [cited by applicant]
US 20220226314A1 · Pinchman et al. · 2022 [cited by applicant]
US 20240180899A1 · Pinchman et al. · 2024 [cited by applicant]
CN 1906183A · 2007 [cited by applicant]
CN 101798292 · 2010 [cited by applicant]
CN 104131034 · 2014 [cited by applicant]
CN 106565706 · 2017 [cited by applicant]
CN 106608895 · 2017 [cited by applicant]
CN 106749233 · 2017 [cited by applicant]
CN 106957315 · 2017 [cited by applicant]
CN 107089981 · 2017 [cited by applicant]
JP 2003096461 · 2003 [cited by applicant]
RU 2542994C2 · 2014 [cited by applicant]
RU 2554346C2 · 2015 [cited by applicant]
RU 262105202 · 2017 [cited by applicant]
WO WO2002024636 · 2002 [cited by applicant]
WO WO2003089441 · 2003 [cited by applicant]
WO WO2005049593 · 2005 [cited by applicant]
WO WO2005049594 · 2005 [cited by applicant]
WO WO2005079803 · 2005 [cited by applicant]
WO WO2006093346 · 2006 [cited by applicant]
WO WO2008008374 · 2008 [cited by applicant]
WO WO2008030836 · 2008 [cited by applicant]
WO WO2008033747 · 2008 [cited by applicant]
WO WO2008064116 · 2008 [cited by applicant]
WO WO2009036051A1 · 2009 [cited by examiner]
WO WO2010065824 · 2010 [cited by applicant]
WO WO2010065865 · 2010 [cited by applicant]
WO WO2010083442 · 2010 [cited by applicant]
WO WO2010138588 · 2010 [cited by applicant]
WO WO2010148422 · 2010 [cited by applicant]
WO WO2011021038 · 2011 [cited by applicant]
WO WO2011068561 · 2011 [cited by applicant]
WO WO2011149492 · 2011 [cited by applicant]
WO WO2011150016 · 2011 [cited by applicant]
WO WO2012058392 · 2012 [cited by applicant]
WO WO2012063085 · 2012 [cited by applicant]
WO WO2013185202 · 2013 [cited by applicant]
WO WO2014113413 · 2014 [cited by applicant]
WO WO2014165044 · 2014 [cited by applicant]
WO WO2014189393 · 2014 [cited by applicant]
WO WO2015003816 · 2015 [cited by applicant]
WO WO2015085238 · 2015 [cited by applicant]
WO WO2015158299 · 2015 [cited by applicant]
WO WO2016025652 · 2016 [cited by applicant]
WO WO2016127135 · 2016 [cited by applicant]
WO WO2016131100 · 2016 [cited by applicant]
WO WO2016172194 · 2016 [cited by applicant]
WO WO2016188935 · 2016 [cited by applicant]
WO WO2017017469 · 2017 [cited by applicant]
WO WO2017044720 · 2017 [cited by applicant]
WO WO2017101851 · 2017 [cited by applicant]
WO WO2017123616 · 2017 [cited by applicant]
WO WO2017132474 · 2017 [cited by applicant]
WO WO2017184995 · 2017 [cited by applicant]
WO WO2017214491 · 2017 [cited by applicant]
WO WO2018026646A1 · 2018 [cited by examiner]
WO WO2018127130 · 2018 [cited by applicant]
WO WO2018146506 · 2018 [cited by applicant]
WO WO2019139899 · 2019 [cited by applicant]
WO WO2019139900 · 2019 [cited by applicant]
WO WO2019139902 · 2019 [cited by applicant]
WO WO2019139907 · 2019 [cited by applicant]
WO WO2019210828 · 2019 [cited by applicant]
WO WO2020061216 · 2020 [cited by applicant]
Ruzicka, L., et al. (1948), Veilchenriechstoffe. 26. Mitteilung. Synthese des 1,1,7-Trimethyl-3-(buten-31-ylon-33)-cyclohepten-(2), eines 7-gliedrigen Analogons des β-Irons. Helvetica Chimica Acta, 31: 422-438. https://… [cited by applicant]
Extended European Search Report issued in European Patent Application No. 25150549.1, dated Apr. 22, 2025. [cited by applicant]
Bellkov V.G., Pharmaceutical chemistry, educational allowance, 2007, Moscow, MEDpress-inform, pp. 27-29. [cited by applicant]
Durnov L.A. et al., Pediatric oncology, Second edition, Moscow: Medicine Publishing House, 2002, p. 139. [cited by applicant]
Dyson G. et al., Chemistry of Synthetic Drugs substances, ed. Mir, Moscow, 1964, pp. 12-19. [cited by applicant]
Kümmerer, K., Pharmaceuticals in the environment, Annual Review of Environment and Resources, 2010, v. 35, p. 57-75, doi:10.1146/annurev-environ-052809-161223 (abstract, p. 60). [cited by applicant]
Mashkovsky M.D., “Medicinal funds”, Moscow, “Medicine”, 1993, part I, p. 8. [cited by applicant]
Office Action issued in Mexican Patent Application No. MX/a/2020/007388, dated Apr. 21, 2022. [cited by applicant]
Office Action issued in Mexican Patent Application No. MX/a/2020/007388, dated Aug. 31, 2022. [cited by applicant]
Office Action issued in Chinese Patent Application No. 201980016882.X, dated Aug. 26, 2022. [cited by applicant]
Office Action Issued in Russian Patent Application No. 2020120933, dated Oct. 21, 2022. [cited by applicant]
Office Action issued in Japanese Patent Application No. 2020-538691, dated Feb. 2, 2023. [cited by applicant]
Office Action Issued in New Zealand Patent Application No. 765825, dated Feb. 7, 2023. [cited by applicant]
Office Action issued in Mexican Patent Application No. MX/a/2020/007388, dated Feb. 15, 2023. [cited by applicant]
Office Action issued in Taiwan Patent Application No. 108101048, dated Jan. 4, 2023. [cited by applicant]
Office Action issued in Japanese Patent Application No. 2020-538691, dated May 16, 2023. [cited by applicant]
Office Action issued in Australian Patent Application No. 2019207608, dated Jun. 8, 2023. [cited by applicant]
|International Search Report dated Apr. 1, 2019 for PCT/US2019/012719, filed Jan. 8, 2019. [cited by applicant]
International Search Report dated Apr. 10, 2019 for PCT/US2019/012695, filed Jan. 8, 2019. [cited by applicant]
International Preliminary Report on Patentability dated Jul. 23, 2020 for PCT/US2019/012704, filed Jan. 8, 2019. [cited by applicant]
International Preliminary Report on Patentability dated Jul. 23, 2020 for PCT/US2019/012719, filed Jan. 8, 2019. [cited by applicant]
International Preliminary Report on Patentability dated Jul. 23, 2020 for PCT/US2019/012695, filed Jan. 8, 2019. [cited by applicant]
Extended European Search Report dated Aug. 12, 2021 for EP 19 738 922.4. [cited by applicant]
Written Opinion and Search Report for Singapore Application No. 11202005785X, dated Jan. 6, 2022. [cited by applicant]
Written Opinion and Search Report for Singapore Application No. 11202005784Y, dated Jan. 6, 2022. [cited by applicant]
Office Action issued in Mexican Patent Application No. MX/a/2020/007392, dated Apr. 21, 2022. [cited by applicant]
Office Action issued in Mexican Patent Application No. MX/a/2020/007014, dated Apr. 19, 2022. [cited by applicant]
|Office Action issued in Mexican Patent Application No. MX/a/2023/009185, dated May 15, 2024. [cited by applicant]
Office Action issued in Mexican Patent Application No. MX/a/2023/009185, dated Sep. 23, 2024. [cited by applicant]
Office Action issued in Japanese Patent Application No. 2023-156385, dated Nov. 26, 2024. [cited by applicant]
Office Action issued in Taiwan Patent Application No. 113101066, dated Dec. 4, 2024. [cited by applicant]
Examiner's Report issued in Canadian Patent Application No. 3,087,261, dated Feb. 7, 2025. [cited by applicant]
Office Action issued in Chinese Patent Application No. 201980016882.X, dated Apr. 19, 2023. [cited by applicant]
Office Action issued in Chinese Patent Application No. 201980016882.X, dated Jul. 27, 2023. [cited by applicant]
Written Opinion for Singaporean Patent Application No. 11202005985P, dated Aug. 4, 2023. [cited by applicant]
Office Action issued in New Zealand Patent Application No. 765825, dated Aug. 4, 2023. [cited by applicant]
Office Action issued in Brazilian Patent Application No. BR 11 2020 014169 0, dated Jun. 5, 2023. [cited by applicant]
Second Office Action for Indian Application No. 202017026070, dated Dec. 19, 2023. [cited by applicant]
Office Action issued in Korean Patent Application No. 10-2020-7022538, dated Feb. 13, 2024. [cited by applicant]
Shipra, G. et al., “Identification of Novel Potent Inhibitors Against Bcl-xL Anti-apoptotic Protein Using Docking Studies” vol. 19, No. 12, 2012, pp. 1302-1317. [cited by applicant]
Bruncko, M. et al., “Studies Leading to Potent, Dual Inhibitors of Bcl-2 and Bcl-XI” [cited by applicant]
International Search Report for PCT/US2019/012695, dated Jan. 8, 2019. [cited by applicant]
Aguilar, A. et al, “A Potent and Highly Efficacious Bcl-2/Bcl-xL Inhibitor” Journal of Medicinal Chemistry (2013), 56(7), 3048-3067. [cited by applicant]
Almerico, A. et al, “3D-QSAR pharmacophore modeling and in silico screening of new Bcl-xl inhibitors” European Journal of Medicinal Chemistry, (2010),(11), 4774-4782. [cited by applicant]
Bai, L. et al, “BM-1197: a novel and specific Bcl-2/Bcl-xL inhibitor inducing complete and long-lasting tumor regression in vivo” PLoS One (2014), 9(6), e99404/1-e99404/13, 13 pp. [cited by applicant]
Bernardo P. et al, “Structure-Activity Relationship Studies of Phenanthridine-Based Bcl-XL Inhibitors” J Med Chem, (2008), 51(21), 6699-6710. [cited by applicant]
Chen, J. et al, “Structure-Based Discovery of BM-957 as a Potent Small-Molecule Inhibitor of Bcl-2 and Bcl-xL Capable of Achieving Complete Tumor Regression” Journal of Medicinal Chemistry (2012), 55(19), 8502-8514. [cited by applicant]
Giedt R. et al, “Imaging Cellular Distribution of Bcl Inhibitors Using Small Molecule Drug Conjugates” Bioconjugate Chemistry (2014), 25(11), 2081-2085. [cited by applicant]
Hou, X. et al, “3D-QSAR study on a series of Bcl-2 protein inhibitors using comparative molecular field analysis” Protein & Peptide Letters (2011), 18(5), 440-449. [cited by applicant]
Kastritis, P. et al, “A Biophysical Model for Predicting the Binding Affinity of Protein-Protein Interaction Inhibitors” Journal of Chemical Information and Modeling (2014), 54(3), 826-836. [cited by applicant]
Lee, E. et al, “Conformational Changes in Bcl-2 Pro-survival Proteins Determine their Capacity to Bind Ligands” Journal of Biological Chemistry (2009), 284(44), 30508-30517. [cited by applicant]
Mabrouk, M. “Discovering best candidates for hepatocellular carcinoma(HCC) by in-silico techniques and tools” Int. J. Bioinfo. Res. and Appl.,(2012), 8(1/2), 141-152. [cited by applicant]
Magee, Thomas V., “Progress in discover of small-molecule modulators of protein-protein interactions via fragment screeing” Bioorganic & Medicinal Chemistry Letters, 2015, 25(12), 2461. [cited by applicant]
Park, C-M. et al, “Discovery of an Orally Bioavailable Small Molecule Inhibitor of Prosurvival B-Cell Lymphoma 2 Proteins” J Med Chem, (2008), 51(21), 6902-6915. [cited by applicant]
Shipra, G. et al., “Identification of Novel Potent Inhibitors Against Bcl-xL Anti-apoptotic Protein Using Docking Studies” Protein & Peptide Letters 19(12), 2012, pp. 1302-1317. [cited by applicant]
Varnes, J. et al, “Towards the next generation of dual Bcl-2/Bcl-xL inhibitors” Bioorganic & Medicinal Chemistry Letters (2014), 24(14), 3026-3033. [cited by applicant]
Ye, L. et al, “The small-molecule compound BM-1197 inhibits the antiapoptotic regulators Bcl-2/Bcl-xL and triggers apoptotic cell death in human colorectal cancer cells” Tumor Biology (2015), 36(5), 3447-3455. [cited by applicant]
Zhou, H. et al, “Structure-Based Design of Potent Bcl-2/Bcl-xL Inhibitors with Strong in Vivo Antitumor Activity” Journal of Medicinal Chemistry (2012), 55(13), 6149-6161. [cited by applicant]
Zhou, H. et al, “Design of Bcl-2 and Bcl-xL Inhibitors with Subnanomolar Binding Affinities Based upon a New Scaffold” Journal of Medicinal Chemistry (2012), 55(10), 4664-4682. [cited by applicant]
Zhou, H. et al, “Correction to Design of Bcl-2 and Bcl-xL Inhibitors with Subnanomolar Binding Affinities Based upon a New Scaffold” Journal of Medicinal Chemistry (2012), 55(12), 5987. [cited by applicant]
Extended European Search Report for EP 19 738 922.4, dated Oct. 8, 2021. [cited by applicant]
Auberson, Y. et al, “Improving Nonspecific Binding and Solubility: Bicycloalkyl Groups and Cubanes as para-Phenyl Bioisosteres” ChemMedChem (2017), 12, 590-598. [cited by applicant]
Written Opinion and Search Report for Singapore Application No. 11202005985P, dated Jan. 6, 2022. [cited by applicant]
First Examination Report for Indian Application No. 202017026070, dated Jan. 27, 2022. [cited by applicant]