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US 10,544,100 B2Granted
Autophagy inhibitors
AssigneesThe Translational Genomics Research Institute, Van Andel Research Institute
InventorsJeffrey Paul MacKeigan, Katie Renee Martin, Megan Lynne Goodall, Stephen T. Gately, Tong Wang
Life of this patent
Estimating the term…
Abstract
The present invention relates to compounds of formulas III and V that are useful as pharmaceutical agents, particularly as autophagy inhibitors.
Claims14
A compound of formula III
- or a pharmaceutically acceptable salt thereof, wherein:
- Q is —CH;
- RN is —H;
- R1 is —H, —F, —Cl, —Br, or —CF3;
- R2 is —CH(R2-1)-(CH2)n2—X;
- R2-1 is —H, or —C3 cycloalkyl;
- n2 is 3;
- X is —NX1-2X1-3, wherein
- X1-2 is —H, linear or branched —C1-C4 alkyl, -cyclopropyl, -cyclobutyl, or —SO2—X1-4, wherein X1-4 is selected from the group consisting of:
- —H, —C1-C3 alkyl, and —CO—X1-4, wherein X1-4 is as defined above;
- X1-3 is linear or branched —C1-C4 alkyl substituted with one cyclopropyl;
- R3 is —H, —CF3, —OR3-1, wherein R3-1 is —H, —C1-C6 alkyl, —CO—R3-2, wherein R3-2 is —C1-C3 alkyl or -phenyl, —N(R3-1)2, wherein the R3-1 are the same or different and are as defined above, —SR3-1, wherein R3-1 is as defined above, —S(O)—R3-1 wherein R3-1 is as defined above, or —SO2—R3-1, wherein R3-1 is as defined above;
- R4 is —H, —F, —Cl, —Br, —CF3, —OR4-1, wherein R4-1 is —H, C1-C6 alkyl or —CO—R4-2, wherein R4-2 is C1-C3 alkyl or phenyl, —N(R4-1)2, wherein the R4-1 are the same or different and are as defined above, —SR4-1, wherein R4-1 is as defined above, —S(O)—R4-1, wherein R4-1 is as defined above, or —SO2—R4-1, wherein R4-1 is as defined above;
- and
- R5 is —H, —F, —Cl, —Br, —CF3, —OR5-1, wherein R5-1 is —H, —C1-C6 alkyl or —CO—R5-2 wherein R5-2 is —C1-C3 alkyl or -phenyl, —N(R5-1)2, wherein the R5-1 are the same or different and are as defined above, —SR5-1, wherein R5-1 is as defined above, —S(O)—R5-1, wherein R5-1 is as defined above, or —SO2—R5-1, wherein R5-1 is as defined above;
- with the proviso that one of R1, R3, R4 and R5 must be other than —H.
13 more elements
A compound selected from the group consisting of:
- Example
- Structure
- Name
- 10
- N1-(6-Chloro-2- methoxyacridin-9-yl)-N4- (cyclopropylmethyl)-N4- methylbutane-1,4-diamine
- 12
- N1-(6-Chloro-2- methoxyacridin-9-yl)-N4- cyclopropyl-N4-ethylbutane- 1,4-diamine
- 13
- N1-(6-Chloro-2- methoxyacridin-9-yl)-N4- (cyclopropylmethyl)-N4- ethylbutane-1,4-diamine
- 30
- N1-(acridin-9-yl)-N4- (cyclopropylmethyl)-N4- methylbutane-1,4-diamine
- 31
- N1-(cyclopropylmethyl)-N4- (2-fluoroacridin-9-yl)-N1- methylbutane-1,4-diamine
- 32
- N1-(2-chloroacridin-9-yl)-N4- (cyclopropylmethyl)-N4- methylbutane-1,4-diamine
- 33
- N1-(cyclopropylmethyl)-N4- (2-methoxyacridin-9-yl)-N1- methylbutane-1,4-diamine
- 34
- N1-(6-bromo-2- methoxyacridin-9-yl)-N4- (cyclopropylmethyl)-N4- methylbutane-1,4-diamine
- 35
- N1-(cyclopropyl-methyl)-N4- (6-fluoro-2-methoxyacridin-9- yl)-N1-methylbutane-1,4- diamine
- 36
- N1-(6-chloro-2-fluoroacridin- 9-yl)-N4-(cyclopropylmethyl)- N4-methylbutane-1,4-diamine
- 37
- N1-(cyclopropylmethyl)-N4- (2,6-dichloroacridin-9-yl)-N1- methylbutane-1,4-diamine
- 38
- N1-(3-chloroacridin-9-yl)-N4- (cyclopropylmethyl)-N4- methylbutane-1,4-diamine
- 41
- N1-(cyclopropylmethyl)-N4-(2,7- dichlorobenzo[b][1,5]naphthyridin- 10-yl)-N1-methylbutane-1,4- diamine
- 49
- N4-(6-chloro-2-methoxyacridin-9- yl)-N1-(cyclopropylmethyl)-5- methoxy-N1-methylpentane-1,4- diamine
- 53
- N-(4-(6-chloro-2-methoxyacridin- 9-ylamino)butyl)-N- (cyclopropylmethyl) methanesulfonamide
- 54
- N1-(6-chloro-2- methoxyacridin-9-yl)-N4- (cyclopropylmethyl)butane- 1,4-diamine
- 56
- N1-(6-chloro-2-methoxyacridin-9- yl)-N4-cyclopropyl-N4- methylbutane-1,4-diamine.
34 more elements
Dependencies are inferred from the claim text.