Carbazole-containing sulfonamides as cryptochrome modulators
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C07D-405/12
C07D-405/14
C07D-403/12
C07D-401/12
C07D-413/12
C07D-417/12
C07D-493/08
C07D-209/86
C07D-209/88
A61K-031/403
A61K-031/541
A61K-031/549
A61K-031/404
A61K-031/428
A61K-031/454
A61K-031/5415
G01N-033/68
A61K-031/4155
A61K-031/427
A61K-045/06
C07D-417/06
C07D-401/06
C07D-403/06
C07D-409/12
출원번호
US-0994005
(2016-01-12)
등록번호
US-9775845
(2017-10-03)
발명자
/ 주소
Bersot, Ross
Humphries, Paul
출원인 / 주소
Reset Therapeutics, Inc.
대리인 / 주소
Cooley LLP
인용정보
피인용 횟수 :
1인용 특허 :
85
초록▼
The subject matter herein is directed to carbazole-containing sulfonamide derivatives and pharmaceutically acceptable salts or hydrates thereof of structural formula I wherein the variable R1, R2, R3, R4, R5, R6, R7, A, B, C′, D, E, F, G, H′, a, and b are accordingly described. Also provided are pha
The subject matter herein is directed to carbazole-containing sulfonamide derivatives and pharmaceutically acceptable salts or hydrates thereof of structural formula I wherein the variable R1, R2, R3, R4, R5, R6, R7, A, B, C′, D, E, F, G, H′, a, and b are accordingly described. Also provided are pharmaceutical compositions comprising the compounds of formula I to treat a Cry-mediated disease or disorder, such as diabetes, obesity, metabolic syndrome, Cushing's syndrome, and glaucoma.
대표청구항▼
1. A compound of formula I or an enantiomer thereof, or a pharmaceutically acceptable salt or hydrate thereof, whereineach of A, B, C′, D, E, F, G, and H′ is carbon;each of R1 and R2, is independently selected from the group consisting of hydrogen, halogen, cyano, nitro, —CF3, —CHF2, —CH2F, trifluor
1. A compound of formula I or an enantiomer thereof, or a pharmaceutically acceptable salt or hydrate thereof, whereineach of A, B, C′, D, E, F, G, and H′ is carbon;each of R1 and R2, is independently selected from the group consisting of hydrogen, halogen, cyano, nitro, —CF3, —CHF2, —CH2F, trifluoromethoxy, azido, hydroxyl, (C1-C6)alkoxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, —(C═O)—R8, —(C═O)—O—R8, —O—(C═O)—R8, —NR8(C═O)—R10, —(C═O)—NR8R9, —NR8R9, —NR8OR9, —S(O)cNR8R9, —S(O)d(C1-C8)alkyl, —O—SO2—R8, —(CR8R9)d(3-10)-membered cycloalkyl, —(CR8R9)e(C6-C10)aryl, —(CR8R9)e(4-10)-membered heterocyclyl, —(CR8R9)f(C═O)(CR8R9)e(C6-C10)aryl, —(CR8R9)f(C═O)(CR8R9)e(4-10)-membered heterocyclyl, —(CR8R9)eO(CR8R9)f(C6-C10)aryl, —(CR8R9)eO(CR8R9)f(4-10)-membered heterocyclyl, —(CR8R9)fS(O)d(CR8R9)e(C6-C10)aryl, and —(CR8R9)fS(O)d(CR8R9)e(4-10)-membered heterocyclyl;each of R3 and each of R5 is independently selected from the group consisting of hydrogen, cyano, —CF3, —CHF2, —CH2F, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, —(C═O)—R8, —(C═O)—O—R8, —(C═O)—NR8R9, —S(O)cNR8R9, —S(O)d(C1-C8)alkyl, —(CR8R9)d(3-10)-membered cycloalkyl, —(CR8R9)e(C6-C10)aryl, —(CR8R9)e(4-10)-membered heterocyclyl, —(CR8R9)f(C═O)(CR8R9)e(C6-C10)aryl, —(CR8R9)f(C═O)(CR8R9)e(4-10)-membered heterocyclyl, —(CR8R9)eO(CR8R9)f(C6-C10)aryl, —(CR8R9)eO(CR8R9)f(4-10)-membered heterocyclyl, —(CR8R9)fS(O)d(CR8R9)e(C6-C10)aryl, and —(CR8R9)fS(O)d(CR8R9)e(4-10)-membered heterocyclyl;wherein each of the R3 groups are optionally linked to each other as a 4-12 membered mono- or bicyclic ring;wherein each of the R5 groups are optionally linked to each other as a 4-12 membered mono- or bicyclic ring;R4 is selected from the group consisting of hydrogen, —CF3, —CHF2, —CH2F, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, —(C═O)—R8, —(C═O)—O—R8, —(C═O)—NR8R9, —(CR8R9)d(3-10)-membered cycloalkyl, —(CR8R9)e(C6-C10)aryl, —(CR8R9)e(4-10)-membered heterocyclyl, —(CR8R9)f(C═O)(CR8R9)e(C6-C10)aryl, —(CR8R9)f(C═O)(CR8R9)e(4-10)-membered heterocyclyl, —(CR8R9)eO(CR8R9)f(C6-C10)aryl, —(CR8R9)eO(CR8R9)f(4-10)-membered heterocyclyl, —(CR8R9)fS(O)d(CR8R9)e(C6-C10)aryl, and —(CR8R9)fS(O)d(CR8R9)e(4-10)-membered heterocyclyl;R6 is selected from the group consisting of hydrogen, —CF3, —CHF2, —CH2F, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, —(C═O)—R8, —(C═O)—O—R8, —(C═O)—NR8R9, —(CR8R9)d(3-10)-membered cycloalkyl, —(CR8R9)e(C6-C10)aryl, —(CR8R9)e(4-10)-membered heterocyclyl, —(CR8R9)f(C═O)(CR8R9)e(C6-C10)aryl, —(CR8R9)f(C═O)(CR8R9)e(4-10)-membered heterocyclyl, —(CR8R9)eO(CR8R9)f(C6-C10)aryl, —(CR8R9)eO(CR8R9)f(4-10)-membered heterocyclyl, —(CR8R9)fS(O)d(CR8R9)e(C6-C10)aryl, and —(CR8R9)fS(O)d(CR8R9)e(4-10)-membered heterocyclyl;wherein one R5 group and R6 are optionally linked to each other as a 4-12 membered mono- or bicyclic ring;R7 is selected from the group consisting of —CF3, —CHF2, —CH2F, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, —(C═O)—R8, —(C═O)—O—R8, —NR8(C═O)—R10, —(C═O)—NR8R9, —NR8R9, —NR8OR9, —(CR8R9)d(3-10)-membered cycloalkyl, —(CR8R9)e(4-10)-membered heterocyclyl, —(CR8R9)f(C═O)(CR8R9)e(C6-C10)aryl, —(CR8R9)f(C═O)(CR8R9)e(4-10)-membered heterocyclyl, —(CR8R9)eO(CR8R9)f(C6-C10)aryl, —(CR8R9)eO(CR8R9)f(4-10)-membered heterocyclyl, —(CR8R9)fS(O)d(CR8R9)e(C6-C10)aryl, and —(CR8R9)fS(O)dS(CR8R9)e(4-10)-membered heterocyclyl;R6 and R7 can be linked to each other as a 4-12 membered mono- or bicyclic ring optionally substituted with 1 or more halogen, (C1-C6)alkyl, (C1-C6)alkoxy, or (3-10)-membered cycloalkyl;each of R8, R9 and R10 are independently selected from the group consisting of hydrogen, (C1-C6)alkyl, —(CR11R12)e(3-10)-membered cycloalkyl, —(CR11R12)g(C6-C10)aryl, and —(CR11R12)g(4-10)-membered heterocyclyl;any carbon atoms of the (C1-C6)alkyl, the (3-10)-membered cycloalkyl, the (C6-C10)aryl and the (4-10)-membered heterocyclyl of the foregoing R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R15, and R16 are independently optionally substituted with 1 to 3 R14 substituents each independently selected from the group consisting of halogen, cyano, nitro, —CF3, —CHF2, —CH2F, trifluoromethoxy, azido, hydroxyl, —O—R15, (C1-C6)alkoxy, —(CR8R9)e(C1-C6)alkoxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, —(C═O)—R11, —(C═O)—R15, —(C═O)—O—R11, —(C═O)—O—R15, —O—(C═O)—R11, —O—(C═O)—R15, —NR11(C═O)—R13, —(C═O)—NR11R12, —(C═O)—NR11R15, —NR11R12, —NR11R15, —NR11OR12, —NR11OR15, —S(O)cNR11R12, —S(O)cNR11R15, —S(O)d(C1-C6)alkyl, —S(O)dR15, —O—SO2—R11, —O—SO2—R15, —(CR11R12)e(3-10)-membered cycloalkyl, —(CR11R12)e(C6-C10)aryl, —(CR11R12)e(4-10)-membered heterocyclyl, —(CR11R12)f(C═O)(CR11R12)e(C6-C10)aryl, —(CR11R12)f(C═O)(CR11R12)e(4-10)-membered heterocyclyl, —(CR11R12)eO(CR11R12)f(C6-C10)aryl, —(CR11R12)eO(CR11R12)f(4-10)-membered heterocyclyl, —(CR11R12)fS(O)d(CR11R12)e(C6-C10)aryl, and —(CR11R12)fS(O)d(CR11R12)e(4-10)- membered heterocyclyl;any carbon atoms of the (C1-C6)alkyl, the (3-10)-membered cycloalkyl, the (C6-C10)aryl and the (4-10)-membered heterocyclyl of the foregoing R14 are independently optionally substituted with 1 to 3 R16 substituents each independently selected from the group consisting of halogen, cyano, nitro, —CF3, —CHF2, —CH2F, trifluoromethoxy, azido, (CH2)eOH, (C1-C6)alkoxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, —(C═O)—R11, —(C═O)—R15, —(C═O)—O—R11, —(C═O)—O—R15, —O—(C═O)—R11, —O—(C═O)—R15, —NR11(C═O)—R13, —(C═O)—NR11R12, —NR11R12, and —NR11R15;any nitrogen atoms of the (4-10)-membered heterocyclyl of the foregoing R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R14, and R15 are independently optionally substituted with (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, —(C═O)—R11, —(C═O)—O—R11, —(C═O)—NR11R12, —(CR11R12)e(3-10)- membered cycloalkyl, —(CR11R12)e(C6-C10)aryl, —(CR11R12)f(4-10)-membered heterocyclyl, —(CR11R12)f(C═O)(CR11R12)e(C6-C10)aryl, or —(CR11R12)f(C═O)(CR11R12)e(4-10)-membered heterocyclyl;each R11, R12, and R13 are independently hydrogen or (C1-C6)alkyl;R15 is —(CR11R12)e(3-10)-membered cycloalkyl, —(CR11R12)e(C6-C10)aryl, or —(CR11R12)e(4-10)-membered heterocyclyl;a and b are each independently 1, 2, 3, or 4;c is 1 or 2;d is 0, 1, or 2; ande, f, and g are each independently 0, 1, 2, 3, 4, or 5,and wherein when R7 is (C1-C6)alkyl, R6 is selected from the group consisting of —CF3, —CHF2, —CH2F, (C2-C6)alkenyl, (C2-C6)alkynyl, —(C═O)—R8, —(C═O)—O—R8, —(C═O)—NR8R9, —(CR8R9)d(3-10)-membered cycloalkyl, —(CR8R9)e(4-10)-membered non-aromatic heterocyclyl, —(CR8R9)f(C═O)(CR8R9)e(C6-C10)aryl, —(CR8R9)f(C═O)(CR8R9)e(4-10)-membered heterocyclyl, —(CR8R9)eO(CR8R9)f(C6-C10)aryl, —(CR8R9)eO(CR8R9)f(4-10)-membered heterocyclyl, —(CR8R9)fS(O)d(CR8R9)e(C6-C10)aryl, and —(CR8R9)fS(O)d(CR8R9)e(4-10)-membered heterocyclyl, and wherein the (3-10)-membered cycloalkyl of the (CR8R9)d(3-10)-membered cycloalkyl is optionally substituted with one or more halogen, CF3, CN, (C1-C6)alkyl, or (C1-C6)alkoxy. 2. The compound according to claim 1, wherein each of R1 and R2 is independently selected from hydrogen or halogen; R4 is hydrogen or (C1-C6)alkyl; R3 and R5 are hydrogen; R6 is —CF3, —CHF2, —CH2F, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, —(CR8R9)d(3-10)-membered cycloalkyl, —(CR8R9)e(C6-C10)aryl, —(CR8R9)e(4-10)-membered heterocyclyl, —(CR8R9)eO(CR8R9)f(C6-C10)aryl, —(CR8R9)eO(CR8R9)f(4-10)-membered heterocyclyl, —(CR8R9)fS(O)d(CR8R9)e(C6-C10)aryl, or —(CR8R9)fS(O)d(CR8R9)e(4-10)-membered heterocyclyl; R7 is —CF3, —CHF2, —CH2F, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, —(CR8R9)d(3-10)-membered cycloalkyl, —(CR8R9)e(4-10)-membered heterocyclyl, —(CR8R9)eO(CR8R9)f(C6-C10)aryl, —(CR8R9)eO(CR8R9)f(4-10)-membered heterocyclyl, —(CR8R9)fS(O)d(CR8R9)e(C6-C10)aryl, or —(CR8R9)fS(O)d(CR8R9)e(4-10)-membered heterocyclyl. 3. The compound according to claim 1, wherein each of R1 and R2 is independently selected from hydrogen or halogen; R4 is hydrogen or (C1-C6)alkyl; R3 and R5 are hydrogen; R6 and R7 are linked to each other as a 4-12 membered mono- or bicyclic ring optionally substituted with 1 or more halogen, (C1-C6)alkyl, (C1-C6)alkoxy, or (3-10)-membered cycloalkyl. 4. The compound according to claim 1, wherein each of R1 and R2 is independently selected from hydrogen or halogen; R4 is hydrogen or (C1-C6)alkyl; R3 and one R5 are hydrogen; one R5 and R6 are linked to each other as a 4-12 membered mono- or bicyclic ring; R7 is —CF3, —CHF2, —CH2F, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, —(CR8R9)d(3-10)-membered cycloalkyl, —(CR8R9)e(4-10)-membered heterocyclyl, —(CR8R9)eO(CR8R9)f(C6-C10)aryl, —(CR8R9)eO(CR8R9)f(4-10)-membered heterocyclyl, —(CR8R9)fS(O)d(CR8R9)e(C6-C10)aryl, or —(CR8R9)fS(O)d(CR8R9)e(4-10)-membered heterocyclyl. 5. The compound according to claim 1 wherein the compound is the single enantiomer bearing an (S)-configuration at C-3; each of R1 and R2 is independently selected from hydrogen or halogen; R4 is hydrogen or (C1-C6)alkyl, R3 and R5 are hydrogen; R6 is —CF3, —CHF2, —CH2F, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, —(CR8R9)d(3-10)-membered cycloalkyl, —(CR8R9)e(C6-C10)aryl, —(CR8R9)e(4-10)-membered heterocyclyl, —(CR8R9)eO(CR8R9)f(C6-C10)aryl, —(CR8R9)eO(CR8R9)f(4-10)-membered heterocyclyl, —(CR8R9)fS(O)d(CR8R9)e(C6-C10)aryl, or —(CR8R9)fS(O)d(CR8R9)e(4-10)-membered heterocyclyl; R7 is —CF3, —CHF2, —CH2F, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, —(CR8R9)d(3-10)-membered cycloalkyl, —(CR8R9)e(4-10)-membered heterocyclyl, —(CR8R9)eO(CR8R9)f(C6-C10)aryl, —(CR8R9)eO(CR8R9)f(4-10)-membered heterocyclyl, —(CR8R9)fS(O)d(CR8R9)e(C6-C10)aryl, or —(CR8R9)fS(O)d(CR8R9)e(4-10)-membered heterocyclyl. 6. The compound according to claim 1, wherein the compound is the single enantiomer bearing an (S)-configuration at C-3; each of R1 and R2 is independently selected from hydrogen or halogen; R4 is hydrogen or (C1-C6)alkyl; R3 and R5 are hydrogen; R6 and R7 are linked to each other as a 4-12 membered mono- or bicyclic ring optionally substituted with 1 or more halogen, (C1-C6)alkyl, (C1-C6)alkoxy, or (3-10)-membered cycloalkyl. 7. The compound according to claim 1, wherein said compound modulates Cry1 or Cry2. 8. The compound according to claim 7, wherein said modulation comprises any one of the following: (i) binding to Cry1 or Cry2;(ii) inhibiting modification of Cry1 or Cry2;(iii) altering Cry1 or Cry2 localization;(iv) increasing or decreasing Cry1 or Cry2 stabilization;(v) increasing or decreasing the binding between Cry1 or Cry2 to a target;(vi) increasing or decreasing Cry1 or Cry2 activity; and(vii) increasing or decreasing activity of a Cry1 or Cry2 target. 9. The compound according to claim 8, wherein said target is Per1, Per2, glucocorticoid receptor (GR), CLOCK, BMAL1, or a CLOCK-BMAL1 promoter sequence. 10. A pharmaceutical composition comprising a compound according to claim 1, or a pharmaceutically acceptable salt or hydrate thereof, and a pharmaceutically acceptable carrier, adjuvant, or diluent. 11. The pharmaceutical composition according to claim 10, further comprising one or more additional therapeutic agents.
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