| Sonstiges: |
- Nachgewiesen in: USPTO Patent Applications
- Sprachen: English
- Document Number: 20240173311
- Publication Date: May 30, 2024
- Appl. No: 18/276943
- Application Filed: February 11, 2022
- Claim: 1. A method of treating a subject having a disease or injury comprising administering to the subject a therapeutically effective amount of a compound, wherein the compound is a compound of formula (I): [chemical expression included] or a pharmaceutically acceptable salt or a tautomer thereof, wherein Q is optionally substituted C6-C10 aryl or optionally substituted 6- to 10-membered heterocyclyl; R1 is H, OH, optionally substituted C1-C6 alkyl, optionally substituted C6-C16 aryl, or optionally substituted 6- to 12-membered heteroaryl; and Z is O or NRc and is a double bond, wherein Rc is H; optionally substituted C1-C6 alkyl; optionally substituted C2-C6 alkenyl; optionally substituted C2-C6 alkynyl; optionally substituted C3-C8 cycloalkyl; optionally substituted C4-C13 cycloalkenyl; optionally substituted C1-C15 heterocyclyl; optionally substituted C6-C16 aryl; ORd; SRe; or NRfRg, wherein Ra and Re are independently H or C1-C6 alkyl and wherein Rf and Rg are independently H, optionally substituted C1-C6 alkyl, optionally substituted C3-C8 cycloalkyl, optionally substituted 6- to 10-membered heterocyclyl, or optionally substituted C6-C16 aryl, or Rf and Rg, together with the nitrogen atom to which they are attached, form an optionally substituted 6- to 10-membered heterocyclyl, or Rf and Rg, together with the nitrogen atom to which they are attached, form N═C(R1′)Q′, wherein R1′ is H, OH, optionally substituted C1-C6 alkyl, optionally substituted C6-C16 aryl, or optionally substituted 6- to 12-membered heteroaryl and Q′ is optionally substituted C6-C10 aryl or optionally substituted 6- to 10-membered heterocyclyl; or is a single bond, and R1 and Z, together with the carbon atom to which they are attached, form an optionally substituted oxazolidinyl or optionally substituted thiazolidinyl; or is a single bond, and Z is OH.
- Claim: 2. The method of claim 1, wherein the disease or injury is stroke; congenital hypogonadotropic hypogonadism; cerebral hemorrhage; traumatic brain injury (TBI); spinal cord injury (SCI); peripheral vascular disease (PVD); wounds; bone or cartilage injury; hearing loss; depression; anxiety; post-traumatic stress disorder (PTSD); substance abuse; peripheral nerve injury; hematopoietic disorders; amyotrophic lateral sclerosis (ALS); Alzheimer's disease; Parkinson's disease; heart disease; non-arteritic ischemic optic neuropathy (NAION); retinal artery occlusion; bronchopulmonary dysplasia, muscular dystrophy, anosmia, aging, memory disturbance, or viral infection.
- Claim: 3. The method of claim 2, wherein the disease or injury is stroke, provided that: when Q is optionally substituted C6-C10 aryl, Ri is H, Z is NRc, and Rc is NRfRg, Rf and Rg, together with the nitrogen atom to which they are attached, do not form optionally substituted piperazinyl; when Z is NRc, and Rc is NRfRg, one of Rf and Rg is H, and the other of Rf and Rg is C1-C6 alkyl substituted with one oxo, Rg is not further substituted with unsaturated heterocyclyl; piperazinyl; aryl; oxo; ORk, wherein Rk is aryl or heterocyclyl; or NHRI, wherein Ri is aryl, cycloalkyl, or alkyl substituted with oxo; and when Q is optionally substituted C6-C10 aryl and Z is O, R1 not C1-C6 alkyl substituted with NHRm, wherein Rm is aryl.
- Claim: 4. The method of claim 3, wherein the stroke is acute stroke.
- Claim: 5. The method of claim 3, wherein the stroke is in a recovery phase.
- Claim: 6. The method of claim 2, wherein the disease or injury is congenital hypogonadotropic hypogonadism.
- Claim: 7. The method of claim 6, wherein the congenital hypogonadotropic hypogonadism is Kallmann Syndrome.
- Claim: 8. The method of claim 2, wherein the disease or injury is viral infection.
- Claim: 9. A method of increasing spermatogenesis in a subject comprising administering to a subject a therapeutically effective amount of a compound, wherein the compound is a compound of formula (I): [chemical expression included] or a pharmaceutically acceptable salt or a tautomer thereof, wherein Q is optionally substituted C6-C10 aryl or optionally substituted 6- to 10-membered heterocyclyl; R1 is H, OH, optionally substituted C1-C6 alkyl, optionally substituted C6-C16 aryl, or optionally substituted 6- to 12-membered heteroaryl; and Z is O or NRc and is a double bond, wherein Rc is H; optionally substituted C1-C6 alkyl; optionally substituted C2-C6 alkenyl; optionally substituted C2-C6 alkynyl; optionally substituted C3-C8 cycloalkyl; optionally substituted C4-C13 cycloalkenyl; optionally substituted C1-C15 heterocyclyl; optionally substituted C6-C16 aryl; ORd; SRe; or NRfRg, wherein Ra and Re are independently H or C1-C6 alkyl and wherein Rf and Rg are independently H, optionally substituted C1-C6 alkyl, optionally substituted C3-C8 cycloalkyl, optionally substituted 6- to 10-membered heterocyclyl, or optionally substituted C6-C16 aryl, or Rf and Rg, together with the nitrogen atom to which they are attached, form an optionally substituted 6- to 10-membered heterocyclyl, or Rf and Rg, together with the nitrogen atom to which they are attached, form N═C(R1′)Q′, wherein R1′ is H, OH, optionally substituted C1-C6 alkyl, optionally substituted C6-C16 aryl, or optionally substituted 6- to 12-membered heteroaryl and Q′ is optionally substituted C6-C10 aryl or optionally substituted 6- to 10-membered heterocyclyl; or is a single bond, and R1 and Z, together with the carbon atom to which they are attached, form an optionally substituted oxazolidinyl or optionally substituted thiazolidinyl; or is a single bond, and Z is OH.
- Claim: 10. The method of any one of claims 1-9, wherein the compound is a compound of formula (la): [chemical expression included] or a pharmaceutically acceptable salt thereof.
- Claim: 11. The method of claim 10, wherein R1 is H.
- Claim: 12. The method of claim 10, wherein R1 is C1-C6 alkyl.
- Claim: 13. The method of claim 10, wherein R1 is optionally substituted C6-16 aryl.
- Claim: 14. The method of claim 13, wherein R1 is optionally substituted phenyl.
- Claim: 15. The method of claim 13, wherein R1 is [chemical expression included]
- Claim: 16. The method of claim 10, wherein R1 is optionally substituted 6- to 12-membered heteroaryl.
- Claim: 17. The method of claim 16, wherein R1 is [chemical expression included]
- Claim: 18. The method of any one of claims 1-9, wherein the compound is a compound of formula (Ib): [chemical expression included] or a pharmaceutically acceptable salt or a tautomer thereof.
- Claim: 19. The method of claim 18, wherein R1 is H.
- Claim: 20. The method of claim 18 or 19, wherein Rc is ORd.
- Claim: 21. The method of claim 20, wherein Rc is OH.
- Claim: 22. The method of claim 18 or 19, wherein Rc is optionally substituted C1-C6 alkyl.
- Claim: 23. The method of claim 22, wherein Rc is methyl substituted with one or two optionally substituted C6-C16 aryl or C1-C15 heterocyclyl.
- Claim: 24. The method of claim 16, wherein Rc is [chemical expression included]
- Claim: 25. The method of claim 18 or 19, wherein Rc is optionally substituted C6-C16 aryl.
- Claim: 26. The method of claim 25, wherein Rc is [chemical expression included]
- Claim: 27. The method of claim 18 or 19, wherein Rc is optionally substituted C1-C15 heterocyclyl.
- Claim: 28. The method of claim 27, wherein Rc is [chemical expression included]
- Claim: 29. The method of claim 18 or 19, wherein Rc is optionally substituted C4-C13 cycloalkenyl.
- Claim: 30. The method of claim 29, wherein Rc is [chemical expression included]
- Claim: 31. The method of claim 18 or 19, wherein Rc is NRfRg.
- Claim: 32. The method of claim 31, wherein Rf and Rg are independently H, optionally substituted C1-C6 alkyl, optionally substituted C3-C8 cycloalkyl, optionally substituted 6- to 10-membered heterocyclyl, or optionally substituted C6-C16 aryl.
- Claim: 33. The method of claim 32, wherein Rc is NH2.
- Claim: 34. The method of claim 31, wherein Rf and Rg are independently H or optionally substituted C8-C18 aryl, wherein at least one of Rf and Rg is optionally substituted C6-C16 aryl.
- Claim: 35. The method of claim 34, wherein Rc is [chemical expression included]
- Claim: 36. The method of claim 31, wherein Rf and Rg are independently H or optionally substituted C1-C6 alkyl, wherein at least one of Rf and Rg is optionally substituted C1-C6 alkyl.
- Claim: 37. The method of claim 36, the compound is a compound of formula (Ib-2): [chemical expression included] or a pharmaceutically acceptable salt thereof, wherein Rh is optionally substituted C1-C6 alkyl, optionally substituted C3-C8 cycloalkyl, optionally substituted C6-C16 aryl, or optionally substituted C1-C15 heterocyclyl.
- Claim: 38. The method of claim 37, wherein Rh is optionally substituted C1-C6 alkyl.
- Claim: 39. The method of claim 38, wherein Rh is CH2N(CH3)2.
- Claim: 40. The method of claim 37, wherein Rh is optionally substituted C3-C8 cycloalkyl.
- Claim: 41. The method of claim 40, wherein Rh is [chemical expression included]
- Claim: 42. The method of claim 37, wherein Rh is optionally substituted C6-C14 aryl.
- Claim: 43. The method of claim 42, wherein Rh is [chemical expression included]
- Claim: 44. The method of claim 37, wherein Rh is optionally substituted C1-C15 heterocyclyl.
- Claim: 45. The method of claim 44, wherein Rh is [chemical expression included]
- Claim: 46. The method of claim 31, wherein Rf and Rg are independently H or optionally substituted C3-C8 cycloalkyl, wherein at least one of Rf and Rg is optionally substituted C3-C8 cycloalkyl.
- Claim: 47. The method of claim 46, wherein Rc is [chemical expression included]
- Claim: 48. The method of claim 31, wherein Rf and Rg are independently H or optionally substituted C1-C15 heterocyclyl, wherein at least one of Rf and Rg is optionally substituted C1-C15 heterocyclyl.
- Claim: 49. The method of claim 48, wherein Rc is [chemical expression included]
- Claim: 50. The method of claim 31, wherein Rf and Rg, together with the nitrogen atom to which they are attached, forms an optionally substituted 6- to 10-membered heterocyclyl.
- Claim: 51. The method of claim 50, wherein Rc is [chemical expression included]
- Claim: 52. The method of claim 18 or 19, wherein Rc is N═C(R1′)Q′.
- Claim: 53. The method of claim 52, wherein R1′ is H.
- Claim: 54. The method of claim 52 or 53, wherein Q′ and Q are identical.
- Claim: 55. The method of any one of claims 1 to 9, wherein is a single bond, and Ri and Z, together with the carbon atom to which they are attached, form an optionally substituted oxazolidinyl or optionally substituted thiazolidinyl.
- Claim: 56. The method of claim 55, wherein R1 and Z, together with the carbon atom to which they are attached, form an optionally substituted thiazolidinyl.
- Claim: 57. The method of claim 56, wherein R1 and Z, together with the carbon atom to which they are attached, form [chemical expression included]
- Claim: 58. The method of any one of claims 1 to 57, wherein Q is [chemical expression included] wherein each R2 is independently halo or NRaRb, wherein Ra and Rb are independently H; optionally substituted C1-C6 alkyl; optionally substituted C8-C18 aryl; or SO2Ri, wherein Ri is H or C1-C6 alkyl; or Ra and Rb, together with the nitrogen atom to which they are attached, forms an optionally substituted 5- to 10-membered heterocyclyl; and m is 0 to 5.
- Claim: 59. The method of claim 58, wherein m is 0.
- Claim: 60. The method of claim 58, wherein m is 1.
- Claim: 61. The method of claim 60, wherein Q is [chemical expression included]
- Claim: 62. The method of claim 60, wherein Q is [chemical expression included]
- Claim: 63. The method of claim 60, wherein Q is [chemical expression included]
- Claim: 64. The method of any one of claims 60 to 63, wherein R2 is halo.
- Claim: 65. The method of any one of claims 60 to 63, wherein R2 is NRaRb.
- Claim: 66. The method of claim 65, wherein Ra and Rb are independently H or optionally substituted C1-C6 alkyl.
- Claim: 67. The method of claim 66, wherein R2 is NH2, NH(CH3), NH(CH2CH3), N(CH3)2, N(CH2CH3)2, N(CH2CH2CH3)2, or N(CH2CH2CH2CH3)2.
- Claim: 68. The method of claim 67, wherein R2 is N(CH2CH3)2.
- Claim: 69. The method of claim 65, wherein Ra and Rb, together with the nitrogen atom to which they are attached, forms an optionally substituted 5- to 10-membered heterocyclyl.
- Claim: 70. The method of claim 69, wherein R2 is [chemical expression included]
- Claim: 71. The method of claim 65, wherein Ra and Rb are independently H or optionally substituted c6-C16 aryl.
- Claim: 72. The method of claim 71, wherein R2 is [chemical expression included]
- Claim: 73. The method of claim 65, wherein R2 is NH(SO2CH3).
- Claim: 74. The method of claim 58, wherein m is 2.
- Claim: 75. The method of claim 74, wherein Q is [chemical expression included]
- Claim: 76. The method of any one of claims 1-57, wherein Q is optionally substituted 6- to 10-membered heterocyclyl.
- Claim: 77. The method of claim 76, wherein Q is [chemical expression included]
- Claim: 78. The method of any one of claims 1 to 9, wherein the compound is: [chemical expression included] [chemical expression included] or a pharmaceutically acceptable salt thereof.
- Claim: 79. The method of any one of claims 1 to 9, wherein the compound is: [chemical expression included] [chemical expression included] [chemical expression included] [chemical expression included] or a pharmaceutically acceptable salt thereof.
- Claim: 80. A compound of formula (I′): [chemical expression included] or a pharmaceutically acceptable salt or a tautomer thereof, wherein Q is optionally substituted C6-C10 aryl or optionally substituted 6- to 10-membered heterocyclyl; R1 is H; and Z is NRc and is a double bond, wherein Rc is a group of formula: [chemical expression included] wherein Rh is substituted C3-C8 cycloalkyl or optionally substituted C1-C15 heterocyclyl; or Rc is a group of formula N═C(R1′)Q′, wherein R1′ is H and Q′ is optionally substituted C6-C10 aryl or optionally substituted 6- to 10-membered heterocyclyl; or Rc is a group of formula: [chemical expression included] or is a single bond, and R1 and Z, together with the carbon atom to which they are attached, form an optionally substituted oxazolidinyl or optionally substituted thiazolidinyl.
- Claim: 81. The compound of claim 80, wherein the compound is a compound of formula (Ib′): [chemical expression included] or a pharmaceutically acceptable salt or a tautomer thereof.
- Claim: 82. The compound of claim 81, wherein the compound is a compound of formula (Ib′-2): [chemical expression included] or a pharmaceutically acceptable salt thereof.
- Claim: 83. The compound of claim 82, wherein Rh is C3-C8 cycloalkyl having at least one substituent.
- Claim: 84. The compound of claim 83, wherein Rh is [chemical expression included]
- Claim: 85. The compound of claim 82, wherein Rh is optionally substituted C1-C15 heterocyclyl.
- Claim: 86. The compound of claim 85, wherein Rh is [chemical expression included]
- Claim: 87. The compound of claim 81, wherein Rc is N═C(R1′)Q′.
- Claim: 88. The compound of claim 87, wherein Q′ and Q are identical.
- Claim: 89. The compound of claim 80, wherein Ri and Z, together with the carbon atom to which they are attached, form an optionally substituted oxazolidinyl or optionally substituted thiazolidinyl.
- Claim: 90. The compound of claim 89, wherein R1 and Z, together with the carbon atom to which they are attached, form an optionally substituted thiazolidinyl.
- Claim: 91. The compound of claim 90, wherein R1 and Z, together with the carbon atom to which they are attached, form [chemical expression included]
- Claim: 92. The compound of any one of claims 80 to 91, wherein Q is [chemical expression included] wherein each R2 is independently halo or NRaRb, wherein Ra and Rb are independently H; optionally substituted C1-C6 alkyl; optionally substituted C6-C16 aryl; or SO2Ri, wherein Ri is H or C1-C6 alkyl; or Ra and Rb, together with the nitrogen atom to which they are attached, form an optionally substituted 5- to 10-membered heterocyclyl; and m is 0 to 5.
- Claim: 93. The compound of claim 92, wherein m is 0.
- Claim: 94. The compound of claim 92, wherein m is 1.
- Claim: 95. The compound of claim 94, wherein Q is [chemical expression included]
- Claim: 96. The compound of claim 94, wherein Q is [chemical expression included]
- Claim: 97. The compound of claim 94, wherein Q is [chemical expression included]
- Claim: 98. The compound of any one of claims 94 to 97, wherein R2 is halo.
- Claim: 99. The compound of any one of claims 94 to 97, wherein Rz is NRaRb.
- Claim: 100. The compound of claim 99, wherein Ra and Rb are independently H or optionally substituted C1-C6 alkyl.
- Claim: 101. The compound of claim 100, wherein R2 is NH2, NH(CH3), NH(CH2CH3), N(CH3)2, N(CH2CH3)2, N(CH2CH2CH3)2, or N(CH2CH2CH2CH3)2.
- Claim: 102. The compound of claim 101, wherein R2 is N(CH2CH3)2.
- Claim: 103. The compound of claim 99, wherein Ra and Rb, together with the nitrogen atom to which they are attached, form an optionally substituted 5- to 10-membered heterocyclyl.
- Claim: 104. The compound of claim 103, wherein R2 is [chemical expression included]
- Claim: 105. The compound of claim 99, wherein Ra and Rb are independently H or optionally substituted C6-C16 aryl.
- Claim: 106. The compound of claim 105, wherein R2 is [chemical expression included]
- Claim: 107. The compound of claim 99, wherein R2 is NH(SO2CH3).
- Claim: 108. The compound of claim 92, wherein m is 2.
- Claim: 109. The compound of claim 108, wherein Q is [chemical expression included]
- Claim: 110. The compound of any one of claims 80-91, wherein Q is optionally substituted 6- to 10-membered heterocyclyl.
- Claim: 111. The compound of claim 110, wherein Q is [chemical expression included]
- Claim: 112. The compound of claim 80, wherein the compound is: [chemical expression included] [chemical expression included] or a pharmaceutically acceptable salt thereof.
- Claim: 113. A pharmaceutical composition comprising a compound of any one of claims 80 to 112 or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient.
- Claim: 114. A pharmaceutical composition comprising a compound of formula (I): [chemical expression included] wherein Q is optionally substituted C6-C10 aryl, or optionally substituted 6- to 10-membered heterocyclyl; R1 is H, OH, optionally substituted C1-C6 alkyl, optionally substituted C6-C16 aryl or optionally substituted 6- to 12-membered heteroaryl; and Z is O or NRc, and is a double bond, wherein Rc is H; optionally substituted C1-C6 alkyl; optionally substituted C2-C6 alkenyl; optionally substituted C2-C6 alkynyl; optionally substituted C3-C8 cycloalkyl; optionally substituted C4-C13 cycloalkenyl; optionally substituted C1-C15 heterocyclyl; optionally substituted C6-C16 aryl; ORd; SRe; or NRfRg, wherein Ra and Re are independently H or C1-C6 alkyl and wherein Rf and Rg are independently H, optionally substituted C1-C6 alkyl, optionally substituted C3-C8 cycloalkyl, optionally substituted 6- to 10-membered heterocyclyl, or optionally substituted C6-C16 aryl, or Rf and Rg, together with the nitrogen atom to which they are attached, forms an optionally substituted 6- to 10-membered heterocyclyl, or or Rf and Rg, together with the nitrogen atom to which they are attached, form N═C(R1′)Q′, wherein R1′ is H, OH, optionally substituted C1-C6 alkyl, optionally substituted C6-C16 aryl, or optionally substituted 6- to 12-membered heteroaryl and Q′ is optionally substituted C6-C10 aryl or optionally substituted 6- to 10-membered heterocyclyl; or is a single bond, and R1 and Z, together with the carbon atom to which they are attached, form an optionally substituted oxazolidinyl or optionally substituted thiazolidinyl, or a pharmaceutically acceptable salt or a tautomer thereof, and a pharmaceutically acceptable excipient.
- Claim: 115. The pharmaceutical composition of claim 114, wherein the compound is a compound of formula (la): [chemical expression included] or a pharmaceutically acceptable salt thereof.
- Claim: 116. The pharmaceutical composition of claim 115, wherein R1 is H.
- Claim: 117. The pharmaceutical composition of claim 115, wherein R1 is C1-C6 alkyl.
- Claim: 118. The pharmaceutical composition of claim 115, wherein R1 is optionally substituted C8-16 aryl
- Claim: 119. The pharmaceutical composition of claim 118, wherein R1 is optionally substituted phenyl.
- Claim: 120. The pharmaceutical composition of claim 119, wherein R1 is [chemical expression included]
- Claim: 121. The pharmaceutical composition of claim 115, wherein R1 is optionally substituted 6- to 12-membered heteroaryl.
- Claim: 122. The pharmaceutical composition of claim 121, wherein R1 is [chemical expression included]
- Claim: 123. The pharmaceutical composition of claim 114, wherein the compound is a compound of formula (Ib): [chemical expression included] or a pharmaceutically acceptable salt or a tautomer thereof.
- Claim: 124. The pharmaceutical composition of claim 123, wherein R1 is H.
- Claim: 125. The pharmaceutical composition of claim 123 or 124, wherein Rc is ORd.
- Claim: 126. The pharmaceutical composition of claim 125, wherein Rc is OH.
- Claim: 127. The pharmaceutical composition of claim 123 or 124, wherein Rc is optionally substituted C1-C6 alkyl.
- Claim: 128. The pharmaceutical composition of claim 127, wherein Rc is methyl substituted with one or two optionally substituted C6-C16 aryl or C1-C15 heterocyclyl.
- Claim: 129. The pharmaceutical composition of claim 128, wherein Rc is [chemical expression included]
- Claim: 130. The pharmaceutical composition of claim 123 or 124, wherein Rc is optionally substituted C6-C16 aryl.
- Claim: 131. The pharmaceutical composition of claim 130, wherein Rc is [chemical expression included]
- Claim: 132. The pharmaceutical composition of claim 123 or 124, wherein Rc is optionally substituted C1-C15 heterocyclyl.
- Claim: 133. The pharmaceutical composition of claim 132, wherein Rc is [chemical expression included]
- Claim: 134. The pharmaceutical composition of claim 123 or 124, wherein Rc is optionally substituted C4-C13 cycloalkenyl.
- Claim: 135. The pharmaceutical composition of claim 134, wherein Rc is [chemical expression included]
- Claim: 136. The pharmaceutical composition of claim 123 or 124, wherein Rc is NRfRg.
- Claim: 137. The pharmaceutical composition of claim 136, wherein Rf and Rg are independently H, optionally substituted C1-C6 alkyl, optionally substituted C3-C8 cycloalkyl, optionally substituted 6- to 10-membered heterocyclyl, or optionally substituted C8-C16 aryl.
- Claim: 138. The pharmaceutical composition of claim 137, wherein Rc is NH2.
- Claim: 139. The pharmaceutical composition of claim 136, wherein Rf and Rg are independently H or optionally substituted C8-C16 aryl, wherein at least one of Rf and Rg is optionally substituted C8-C18 aryl.
- Claim: 140. The pharmaceutical composition of claim 139, wherein Rc is [chemical expression included]
- Claim: 141. The pharmaceutical composition of claim 136, wherein Rf and Rg are independently H or optionally substituted C1-C6 alkyl, wherein at least one of Rf and Rg is optionally substituted C1-C6 alkyl.
- Claim: 142. The pharmaceutical composition of claim 141, the compound is a compound of formula (Ib-2): [chemical expression included] or a pharmaceutically acceptable salt thereof, wherein Rh is optionally substituted C1-C6 alkyl, optionally substituted C3-C8 cycloalkyl, optionally substituted C6-C16 aryl, or optionally substituted C1-C15 heterocyclyl.
- Claim: 143. The pharmaceutical composition of claim 142, wherein Rh is optionally substituted C1-C6 alkyl.
- Claim: 144. The pharmaceutical composition of claim 143, wherein Rh is CH2N(CH3)2.
- Claim: 145. The pharmaceutical composition of claim 142, wherein Rh is optionally substituted C3-C8 cycloalkyl.
- Claim: 146. The pharmaceutical composition of claim 145, wherein Rh is [chemical expression included]
- Claim: 147. The pharmaceutical composition of claim 142, wherein Rh is optionally substituted C6-C14 aryl.
- Claim: 148. The pharmaceutical composition of claim 147, wherein Rh is [chemical expression included]
- Claim: 149. The pharmaceutical composition of claim 142, wherein Rh is optionally substituted C1-C15 heterocyclyl.
- Claim: 150. The pharmaceutical composition of claim 149, wherein Rh is [chemical expression included]
- Claim: 151. The pharmaceutical composition of claim 136, wherein Rf and Rg are independently H or optionally substituted C3-C8 cycloalkyl, wherein at least one of Rf and Rg is optionally substituted C3-C8 cycloalkyl.
- Claim: 152. The pharmaceutical composition of claim 151, wherein Rc is [chemical expression included]
- Claim: 153. The pharmaceutical composition of claim 136, wherein Rf and Rg are independently H or optionally substituted C1-C15 heterocyclyl, wherein at least one of Rf and Rg is optionally substituted C1-C15 heterocyclyl.
- Claim: 154. The pharmaceutical composition of claim 153, wherein Rc is [chemical expression included]
- Claim: 155. The pharmaceutical composition of claim 136, wherein Rf and Rg, together with the nitrogen atom to which they are attached, forms an optionally substituted 6- to 10-membered heterocyclyl.
- Claim: 156. The pharmaceutical composition of claim 155, wherein Rc is [chemical expression included]
- Claim: 157. The pharmaceutical composition of claim 123 or 124, wherein Rc is N═C(R1′)Q′.
- Claim: 158. The pharmaceutical composition of claim 157, wherein R1′ is H.
- Claim: 159. The pharmaceutical composition of claim 157 or 158, wherein Q′ and Q are identical.
- Claim: 160. The pharmaceutical composition of claim 114, wherein is a single bond, and R1 and Z, together with the carbon atom to which they are attached, form an optionally substituted oxazolidinyl or optionally substituted thiazolidinyl.
- Claim: 161. The pharmaceutical composition of claim 160, wherein R1 and Z, together with the carbon atom to which they are attached, form an optionally substituted thiazolidinyl.
- Claim: 162. The pharmaceutical composition of claim 161, wherein R1 and Z, together with the carbon atom to which they are attached, form [chemical expression included]
- Claim: 163. The pharmaceutical composition of any one of claims 114 to 162, wherein Q is [chemical expression included] wherein each R2 is independently halo or NRaRb, wherein Ra and Rb are independently H; optionally substituted C1-C6 alkyl; optionally substituted C6-C16 aryl; or SO2Ri, wherein Ri is H or C1-C6 alkyl; or Ra and Rb, together with the nitrogen atom to which they are attached, forms an optionally substituted 5- to 10-membered heterocyclyl; and m is 0 to 5.
- Claim: 164. The pharmaceutical composition of claim 163, wherein m is 0.
- Claim: 165. The pharmaceutical composition of claim 163, wherein m is 1.
- Claim: 166. The pharmaceutical composition of claim 165, wherein Q is [chemical expression included]
- Claim: 167. The pharmaceutical composition of claim 165, wherein Q is [chemical expression included]
- Claim: 168. The pharmaceutical composition of claim 165, wherein Q is [chemical expression included]
- Claim: 169. The pharmaceutical composition of any one of claims 165 to 168, wherein R2 is halo.
- Claim: 170. The pharmaceutical composition of any one of claims 165 to 168, wherein R2 is NRaRb.
- Claim: 171. The pharmaceutical composition of claim 170, wherein Ra and Rb are independently H or optionally substituted C1-C6 alkyl.
- Claim: 172. The pharmaceutical composition of claim 171, wherein R2 is NH2, NH(CH3), NH(CH2CH3), N(CH3)2, N(CH2CH3)2, N(CH2CH2CH3)2, or N(CH2CH2CH2CH3)2.
- Claim: 173. The pharmaceutical composition of claim 172, wherein R2 is N(CH2CH3)2.
- Claim: 174. The pharmaceutical composition of claim 170, wherein Ra and Rb, together with the nitrogen atom to which they are attached, forms an optionally substituted 5- to 10-membered heterocyclyl.
- Claim: 175. The pharmaceutical composition of claim 174, wherein R2 is [chemical expression included]
- Claim: 176. The pharmaceutical composition of claim 170, wherein Ra and Rb are independently H or optionally substituted C6-C16 aryl.
- Claim: 177. The pharmaceutical composition of claim 176, wherein R2 is [chemical expression included]
- Claim: 178. The pharmaceutical composition of claim 170, wherein R2 is NH(SO2CH3).
- Claim: 179. The pharmaceutical composition of claim 163 wherein m is 2.
- Claim: 180. The pharmaceutical composition of claim 179, wherein Q is [chemical expression included]
- Claim: 181. The pharmaceutical composition of any one of claims 114 to 162, wherein Q is optionally substituted 6- to 10-membered heterocyclyl.
- Claim: 182. The pharmaceutical composition of claim 181, wherein Q is [chemical expression included]
- Claim: 183. The pharmaceutical composition of claim 114, wherein the compound is: [chemical expression included] [chemical expression included] or a pharmaceutically acceptable salt thereof.
- Claim: 184. The pharmaceutical composition of claim 114, wherein the compound is: [chemical expression included] [chemical expression included] [chemical expression included] [chemical expression included] or a pharmaceutically acceptable salt thereof.
- Claim: 185. The pharmaceutical composition of any one of claims 114 to 184 for use in the treatment of a disease or injury in a subject.
- Claim: 186. The pharmaceutical composition of claim 185, wherein the disease or injury is stroke; congenital hypogonadotropic hypogonadism; cerebral hemorrhage; traumatic brain injury (TBI); spinal cord injury (SCI); peripheral vascular disease (PVD); wounds; bone or cartilage injury; hearing loss; depression; anxiety; post-traumatic stress disorder (PTSD); substance abuse; peripheral nerve injury; hematopoietic disorders; amyotrophic lateral sclerosis (ALS); Alzheimer's disease; Parkinson's disease; heart disease; non-arteritic ischemic optic neuropathy (NAION); retinal artery occlusion; bronchopulmonary dysplasia, muscular dystrophy, anosmia, aging, memory disturbance, or viral infection.
- Claim: 187. The pharmaceutical composition of claim 186, wherein the disease or injury is stroke, provided that: when Q is optionally substituted C6-C10 aryl, R1 is H, Z is NRc, and Rc is NRRg, Rf and Rg, together with the nitrogen atom to which they are attached, do not form optionally substituted piperazinyl; when Z is NRc, and Rc is NRfRg, one of Rf and Rg is H, and the other of Rf and Rg is C1-C6 alkyl substituted with one oxo, Rg is not further substituted with unsaturated heterocyclyl; piperazinyl; aryl; oxo; ORk, wherein Rk is aryl or heterocyclyl; or NHRI, wherein Ri is aryl, cycloalkyl, or alkyl substituted with oxo; and when Q is optionally substituted Ce-C10 aryl and Z is O, R1 not C1-C6 alkyl substituted with NHRm, wherein Rm is aryl.
- Claim: 188. The pharmaceutical composition of claim 187, wherein the stroke is acute stroke.
- Claim: 189. The pharmaceutical composition of claim 187, wherein the stroke is in a recovery phase.
- Claim: 190. The pharmaceutical composition of claim 186, wherein the disease or injury is congenital hypogonadotropic hypogonadism.
- Claim: 191. The pharmaceutical composition of claim 190, wherein the congenital hypogonadotropic hypogonadism is Kallmann Syndrome.
- Claim: 192. The pharmaceutical composition of claim 186, wherein the disease or injury is viral infection.
- Claim: 193. The pharmaceutical composition of any one of claims 114 to 184 for use in increasing spermatogenesis in a subject.
- Claim: 194. The method of claim 22, wherein the compound is a compound of formula (Ib-1): [chemical expression included] or a pharmaceutically acceptable salt or a tautomer thereof.
- Claim: 195. The compound of claim 81, wherein the compound is a compound of formula (Ib′-1): [chemical expression included] or a pharmaceutically acceptable salt or a tautomer thereof.
- Claim: 196. The pharmaceutical composition of claim 127, wherein the compound is a compound of formula(Ib-1): [chemical expression included] or a pharmaceutically acceptable salt or a tautomer thereof.
- Current International Class: 61; 61; 61; 61; 61; 61; 61; 61; 61; 61
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