IP Library Granted Patent US 11,090,307
Granted Patent B2
US 11,090,307 · App. 16/656,574 · Granted Aug 17, 2021

Treating male senescence

Inventors: Xiaodong Wang (Beijing, CN); Dianrong Li (Beijing, CN); Lingjun Meng (Beijing, CN); Zhiyuan Zhang (Beijing, CN)
Assignee: National Institute of Biological Sciences, Beijing
A61K31/522A61K31/165A61K31/17A61K31/18A61K31/341A61K31/381A61K31/396A61K31/397A61K31/40A61K31/415A61K31/426A61K31/44A61K31/4453A61K31/47A61K31/5375A61P15/08
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Quick Facts
Patent No.
US 11,090,307
App. No.
16/656,574
Granted
Aug 17, 2021
Kind
B2
Abstract

The invention provides methods of treating male reproductive senescence comprising administering to a male in need thereof a necroptosis inhibitor, including inhibitors of RIP1, RIP3 or MLKL. The invention also provides pharmaceutical compositions comprising a necroptosis inhibitor and a second different drug for treating male senescence.

Claims (642)

1. A method of treating male senescence comprising administering to a male in need thereof a necroptosis inhibitor.

2. The method of claim 1 wherein the necroptosis inhibitor is a RIP1, RIP3 or MLKL inhibitor.

3. The method of claim 1 wherein the necroptosis inhibitor is a RIP1 inhibitor.

4. The method of claim 1 wherein the necroptosis inhibitor is a RIP1 inhibitor selected from a compound of Table 1 or Table 2 or Table 3:

Table 1

5-((1H-indol3-yl)methyl)-3-methyl-2-thioxoimidazolidin-4-one (Nec-1)

(S)-phenyl(5-phenyl -4,5-dihydro-1H-pyrazol -1-yl)methanone

5-((1H-indol-3-yl)methyl)-3-methyl-2-thioxoimidazolidin-4-one (Nec-1s)

3-methyl-5-((7-methyl-1H-indol3-yl)methyl)imidazolidine-2,4-dione

(R)-5-((7-chloro-1H-indol3-yl)methyl)-3-methylimidazolidine-2,4-dione

(R)-5-((7-chloro-1H-indol3-yl)methyl)-3-(4-(3-(imidazo[1,2-b]pyridazin-3-ylethynyl)-4-methylphenyl)butyl) imidazolidine-2,4-dione (Ponatinib-Nec1s)

(S)-2,2-dimethyl-1-(5-phenyl-4,5-dihydro-1H-pyrazol-1-yl) propan-1-on (GSK963)

(S)-2,2-dimethyl-1-(5-phenyl-4,5-dihydro-1H-pyrazol-1-yl) propan-1-one

(S)-1-(4-(5-phenyl-4,5-dihydro-1H-pyrazole-1-carbonyl) piperidin-1-yl)ethanone

(S)-2,2-dimethyl-1-(5-(pyridin-2-yl)-4,5-dihydro-1H-pyrazol-1 -yl)propan-1-one

(S)-1-(4-(5-(3 ,5-difluorophenyl)-4,5-dihydro-1H-pyrazol-1 -carbonyl)piperidin-1-yl)ethanone

(S)-5-benzyl-N-(5-methyl-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)isoxazole-3-carboxamide

5-benzyl-N-(5-methyl-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)-4H-1,2,4-triazole-3-carboxamide

(S)-5-benzyl-N-(8-chloro-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)-4H-1,2,4-triazole-3-carboxamide

(S)-5-benzyl-N-(5-methyl-4-oxo-7-(1H-tetrazol-5 -yl)-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl) isoxazole-3-carboxamide

8-bromo-4, 5-dihydro-1H-benzo[b]azepin-2(3H)-one

(S)-5-benzyl-N-(5-methyl-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3 -yl)isoxazole-3 -carboxamide (GSK481)

(S)-5-benzyl-N-(5-methyl-4-oxo-2,3,4,5-tetrahydrobenzo[b]-[1,4]oxazepin-3-yl)-1H-1,2,4-triazole-3-carboxamide (GSK2982772)

1-(4-(4-aminofuro[2,3 -d]pyrimidin-5-yl)phenyl)-3 -(2-fluoro-5-(trifluoromethyl)phenyl)urea (Cpd27)

3-methyl-5-((7-methyl-1H-indol1-3-yl)methyl)imidazolidine-2,4-dione

(R)-5-((7-chloro-1H-indol1-3-yl)methyl)-3-methylimidazolidine-2,4-dione

3 -benzyl-6,7-dihydro-3H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4(5H)-one

N-(3-chloro-2,6-difluorobenzyl)-4-cyclopropyl-1,2,3-thiadiazole-5 -carboxamide

(S)-N-(1-(2-chloro-6-fluorophenyl)ethyl)-5 -cyano-1-methyl-1H-pyrrole-2-carboxamide

(S)-N-(1-(2-chloro-6-fluorophenyl)ethyl)-4-cyclopropyl -1,2, 3-thiadiazole-5-carboxamide

N-Benzyl -N-hydroxy-2,2-dimethylbutanamide

N-(4-Fluorobenzyl)-N-hydroxy-2,2-dimethylbutanamide

N-(2,4-Difluorobenzyl)-N-hydroxy-2,2-dimethylbutanamide

N-(3,4-Difluorobenzyl)-N-hydroxy-2,2-dimethylbutanamide

N-Hydroxy-2,2-dimethyl -N-(2,3,4-trifluorobenzyl)butanamide

N-Hydroxy-2,2-dimethyl -N-(3,4,5-trifluorobenzyl)butanamide

N-Hydroxy-2,2-dimethyl -N-(2,3,5-trifluorobenzyl)butanamide

(2-(3-fluorophenyl)pyrrolidin-1-yl)(1-(trifluoromethyl)cyclopentyl)methanone

(2-(3-fluorophenyl)pyrrolidin-1-yl)(1-(trifluoromethyl)cyclobutyl)methanone

(S)-1-(2,2-dimethylbut-3-enoyl)-4-phenylazetidin-2-one

(S)-2,2-dimethyl-1-(2-phenylazetidin-1-yl)but-3-yn-1-one

(S)-1-(2,2-dimethylbutanoyl)-4-phenylazetidin-2-one,

TABLE 2

1

3

4

5

6

7

8

9

10

11

12

13

14

15

16

17

18

19

20

21

22

23

24

25

26

27

28

29

30

31

32

33

34

35

36

37

38

39

40

41

42

43

44

45

46

47

48

49

50

51

52

53

54

55

56

57

58

59

60

61

62

63

64

65

66

67

68

69

70

71

72

73

74

75

76

77

78

79

80

81

82

83

84

85

86

87

88

89

90

91

92

93

94

95

96

97

98

99

100

101

102

103

104

105

106

107

108

109

110

111

112

113

114

115

116

117

118

119

120

121

122

123

124

125

126

127

128

129

130

131

132

133

134

135

136

137

138

139

140

141

142

143

144

145

146

147

148

149

150

151

S1 

S2 

S3 

S4 

S5 

S6 

S7 

S8 

S9 

S10

S11

S12

S13

S14

S15

S16

S17

S18

S19

S20

TABLE 3

1

2

3

4

5

6

7

8

9

10

11

12

13

14

15

16

17

18

19

20

21

22

23

24

25

26

27

28

29

30

31

32

33

34

35

36

37

38

39

40

41

42

43

44

45

46

47

48

49

50

51

52

53

54

55

56

57

58

59

60

61

62

63

64

65

66

67

68

69

70

71

72

73

74

75

76

77

78

S1

S2

S3

S4

S5

S6

S7

S8

S9

S10

S11

S12

S13

S14

S15

S16

S17

5. The method of claim 1 wherein the necroptosis inhibitor is a RIP3 inhibitor.

6. The method of claim 1 wherein the necroptosis inhibitor is a RIP3 inhibitor selected from a compound of Table 4:

Table 4

tert-butyl 2-(4-(5-(methylcarbamoyl)-1H-benzo[d]imidazol-1-yl)phenyl)acetate (GSK'840)

3-(benzo[d]thiazol-5-yl)-7-(1,3-dimethyl-1H-pyrazol-5-yl)thieno[3,2-c]pyridin-4-amine GSK'843);

N-(6-(isopropylsulfonyl)quinolin-4-yl)benzo[d]thiazol-5-amine (GSK'872);

N-[3-[5-(2-amino-4-pyrimidinyl)-2-(1,1-dimethylethyl)-4-thiazolyl]-2-fluorophenyl]-2,6-difluoro-benzenesulfonamide (Dabrafenib);

3-(2-Imidazo[1,2-b]pyridazin-3-ylethynyl)-4-methyl-N-[4-[4-[(4-methyl-1-piperazinyl)methyl]-3-(trifluoromethyl)phenyl]-benzamide (ponatinib); or

5-[[4-[(2,3-dimethyl-2H-indazol-6-yl)methylamino]-2-pyrimidinyl]amino]-2-methyl-benzenesulfonamide (pazopanib).

7. The method of claim 1 wherein the necroptosis inhibitor is a MLKL inhibitor.

8. The method of claim 1 wherein the necroptosis inhibitor is a MLKL inhibitor selected from a compound of Table 5 or Table 6 or Table 7:

Table 5

(2E)-N-[4-[[(3-Methoxy-2-pyrazinyl)amino]sulfonyl]phenyl]-3-(5-nitro-2-thienyl)-2-propenamide (Necrosulfonamide)

1,3,7-trimethyl-8-(methylsulfonyl)-1H-purine-2,6(3H,7H)-dione (TC13-4)

(2,5-dimethoxybenzylsulfonyl)-1,3,7-trimethyl-1H-purine-2,6(3H,7H)-dione (TC13-58)

7-ethyl-1,3-dimethyl-8-(methylsulfonyl)-1H-purine-2,6(3H,7H)-dione (TC13-74)

1,7-dimethyl-8-(methylsulfonyl)-3-(prop-2-ynyl)-1H-purine-2,6(3H,7H)-dione (TC13-106)

2-(1,7-dimethyl-8-(methylsulfonyl)-2,6-dioxo-1H-purin-3(2H,6H,7H)-yl)acetonitrile (TC13-107)

3-(3-(3-chlorophenyl)prop-2-yn-1-yl)-8-((cyclopropylmethyl) sulfonyl)-1,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione (TC13-119)

8-((2,5-dimethoxybenzyl)sulfonyl)-1,7-dimethyl-3-(3-(2 -(methylamino)pyridin-4-yl)prop-2-yn-1-yl)-3,7-dihydro-1H-purine-2,6-dione (TC13-127)

3-(3-(3-hydroxyphenyl)prop-2-yn-1-yl)-1,7-dimethyl-8-(methylsulfonyl)-3,7-dihydro-1H-purine-2,6-dione (TC13-172)

3-((4-(methyl(4-(3-(4-(trifluoromethoxy)phenyl)ureido)phenyl)amino)pyrimidin-2-yl) amino)benzenesulfonamide (Compound 1)

TABLE 6

1

2

3

4

5

6

7

8

9

10

11

12

13

14

15

16

17

18

19

20

21

22

23

24

25

26

27

28

29

30

31

32

33

34

35

36

37

38

39

40

41

42

43

44

45

46

47

48

49

50

51

52

53

54

55

56

57

58

59

60

61

62

63

64

65

66

67

68

69

70

71

72

73

74

75

76

77

78

79

80

81

82

83

84

85

86

87

88

89

90

91

92

93

94

95

96

97

98

99

100

101

102

103

104

105

106

107

108

109

110

111

112

113

114

115

116

117

118

119

120

121

122

123

124

125

126

127

128

129

130

131

132

133

134

135

136

137

138

139

140

141

142

143

144

145

146

147

148

149

150

151

152

153

154

155

156

157

158

159

160

161

162

163

164

165

166

167

168

169

170

171

172

173

174

175

176

TABLE 7

1

2

3

4

5

6

7

8

9

10

11

12

13

14

15

16

17

18

19

20

21

22

23

24

25

26

27

28

29

30

31

32

33

34

35

36

37

38

39

40

41

42

43

44

45

46

47

48

49

50

51

52

53

54

55

56

57

58

59

60

61

62

63

64

65

66

67

68

69

70

71

72

73

74

75

76

77

78

79

80

81

82

83

84

85

86

87

88

89

90

91

92

93

94

95

96

97

98

99

100

101

102

103

104

105

106

107

108

109

110

111

112

113

114

115

116

117

118

119

120

9. The method of claim 1 wherein the method further comprises administering to the male a second, different drug for treating male senescence.

10. The method of claim 1 wherein the method further comprises administering to the male a second, different drug for treating male senescence, wherein the different drug is selected from an androgen including exogenous and endogenous anabolic androgenic steroids, endogenous androgen stimulators, female hormone inhibitor, growth hormone.

11. The method of claim 1 wherein the method further comprises administering to the male a second, different drug for treating male senescence, wherein the different drug is selected from:

testosterone, prasterone (dehydroepiandrosterone, DHEA), androstenedione (A4), androstenediol (A5), dihydrotestosterone (DHT), 1-Androstenediol, 1-Androstenedione, Bolandiol, Bolasterone, Boldenone, Boldione, Calusterone, Clostebol, Danazol, Dehydrochlormethyltestosterone, Desoxymethyltestosterone, Drostanolone, Ethylestrenol, Fluoxymesterone, Formebolone, Furazabol, Gestrinone, 4-Hydroxytestosterone, Mestanolone, Mesterolone, Metenolone, Methandienone, Methandriol, Methasterone, Methyldienolone, Methyl-1-testosterone, Methylnortestosterone, Methyltestosterone, Metribolone, Mibolerone, Nandrolone, 19-Norandrostenedione, Norboletone, Norclostebol, Norethandrolone, Oxabolone, Oxandrolone, Oxymesterone, Oxymetholone, Prostanozol, Quinbolone, Stanozolol, Stenbolone, 1-Testosterone, Tetrahydrogestrinone, and Trenbolone.

12. The method of claim 1 wherein the male senescence is selected from age-associated low testosterone, low libido, erectile dysfunction, weight gain, reduced muscle mass or tone, and prostate hyperplasia.

13. The method of claim 1 wherein the method further comprises the antecedent step of diagnosis the male senescence.

14. The method of claim 1 wherein the method further comprises the subsequent step of detecting a resultant diminution or reversal of the male senescence.

15. The method of claim 3 wherein the method further comprises the subsequent step of detecting a resultant diminution or reversal of the male senescence.

16. The method of claim 4 wherein the method further comprises the subsequent step of detecting a resultant diminution or reversal of the male senescence.

17. The method of claim 5 wherein the method further comprises the subsequent step of detecting a resultant diminution or reversal of the male senescence.

18. The method of claim 6 wherein the method further comprises the subsequent step of detecting a resultant diminution or reversal of the male senescence.

19. The method of claim 7 wherein the method further comprises the subsequent step of detecting a resultant diminution or reversal of the male senescence.

20. The method of claim 8 wherein the method further comprises the subsequent step of detecting a resultant diminution or reversal of the male senescence.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 18, 2019
From: WANG, XIAODONG; LI, DIANRONG; MENG, LINGJUN; ZHANG, ZHIYUAN
To: NATIONAL INSTITUTE OF BIOLOGICAL SCIENCES, BEIJING
Reel/Frame 050755/0449 →
Priority Claims (1)
WO PCT/CN2017/080746 · Apr 17, 2017 · international
Continuity (2)
Continuation PCTCN2018082934 · Apr 13, 2018
Related Publication 20200046714A1 · Feb 13, 2020
Cited By (1)
US 12,427,149