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US 12,077,495 B2Granted
Compounds for the treatment of acute brain injury
AssigneesKøbenhavns Universitet, Otago Innovation Limited
InventorsAnders Bue Klein, Andrew Neil Clarkson, Joshua Macdonald Houlton, Ulrike Leurs, Rasmus Prætorius Clausen, Bente Frølund, Petrine Wellendorph
Life of this patent
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Abstract
The invention relates to a compound according to formula I wherein when R5 is H, and R1 and R2 form a ring system, then said compound is selected from the following compounds of formula II or formula IV or when R2 is H, and R1 and R5 form a ring system, then said compound has formula III.
Claims19
A compound according to formula I
- or a pharmaceutically acceptance salt thereof, wherein:
- i) R5 is H, R1 and R2 form a ring system, and said compound is selected from:
- or a compound of formula IV:
- wherein:
- n is 1;
- X is selected from O and NH
- Y is selected from NH, O, and CH2
- R3 is selected from H, linear or branched C1-C6 alkyl, benzyl, polyethylenglycolyl,
- R9 is selected from linear and branched C1-C6 alkyl;
- R10 is selected from H, -Me, -Et, —Pr, -iPr, -Bu, -iBu, -tBu, pentyl, neopentyl, and hexyl;
- R4 is selected from H, —C(═O)—C1-C6-alkyl;
- —C(═O)-benzyl, polyethylenglycolyl,
- R11 is selected from linear and branched C1-C6 alkyl;
- each instance of is a bond;
- R12 is selected from H, -Me, -Et, —Pr, -iPr, -Bu, -iBu, -tBu, pentyl, neopentyl, and hexyl;
- R6 and R7 are each independently selected from H, F, Cl, Br, I, aryl, straight linear or branched C1-8 alkyl, —CH2(CH2)p-aryl, —CH═CH-aryl, NH2, NO2, OH, SH, linear or branched —O—C1-8 alkyl, linear or branched —S—C1-8 alkyl, linear or branched —NH—C1-8 alkyl, —O-aryl, —S-aryl, and —NH-aryl;
- wherein aryl optionally includes one or more heteroatoms selected from O, N and S;
- and
- wherein p is 0 or 1;
- or
- ii) R2 is H, R1 and R5 form a ring system, and said compound is a compound of formula IIIb, formula IIIc, or formula IIId:
- wherein:
- n is 0 or 1;
- X is selected from O and NH;
- m is 0 or 1;
- R3 is selected from H, linear or branched C1-C6-alkyl;
- -benzyl, polyethylenglycolyl,
- R9 is selected from linear and branched C1-C6 alkyl;
- R10 is selected from H, -Me, -Et, —Pr, -iPr, -Bu, -iBu, -tBu, pentyl, neopentyl, and hexyl;
- R4 is selected from H, —C(═O)—C1-C6-alkyl;
- —C(═O)-benzyl, polyethylenglycolyl,
- each instance of is a bond;
- R1 is selected from linear and branched C1-C6 alkyl;
- R12 is selected from H, -Me, -Et, —Pr, -iPr, -Bu, -iBu, -tBu, pentyl, neopentyl, and hexyl;
- R13, is selected from H, F, Br, aryl, linear or branched C1-8 alkyl, —CH2(CH2)p-aryl, —CH═CH-aryl, NH2, NO2, OH, SH, linear or branched —O—C2-8 alkyl, linear or branched —S—C1-8 alkyl, linear or branched —NH—C1-8 alkyl, —O-aryl, —S-aryl, and —NH-aryl,
- R14 is selected from H, F, Cl, Br, aryl, linear or branched C1-8 alkyl, —CH2(CH2)p-aryl, —CH═CH-aryl, NH2, OH, SH, linear or branched —O—C1-8 alkyl, linear or branched —S—C1-8 alkyl, linear or branched —NH—C1-8 alkyl, —O-aryl, —S-aryl, and —NH-aryl,
- each aryl optionally includes one or more heteroatoms selected from O, N and S, and wherein each instance of p is independently 0 or 1;
- with the proviso that the compounds of formula IV, when R4 is H or H3 or CH3, then:
- i) R6 and R7 are not both Cl,
- ii) R6 and R7 are not both methyl,
- iii) when R6 is Cl then R7 is not F, and
- iv) when R6 is F then R7 is not Cl . . .
39 more elements
Dependencies are inferred from the claim text.