Short-acting psychoactive compounds of the mdma class
AssigneeApoapsis Holdings, LLC
InventorsDenton W. Hoyer, Robert F. Roscow, Rong Ling, Chuanjun Gao
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Abstract
The present invention is directed to novel chemical compositions of matter, and in particular novel MDMA class of compounds having substituted methylenedioxyphenethylamine and substituted amphetamine, having a metabolically labile thioether group.
Claims44
A compound according to Formula (V) comprising:
- wherein:
- X is S, O, or CH;
- and
- R1 is NR2R3;
- R2 is H or CH3;
- R3 is CH3;
- and
- wherein said dashed lines represents possible double bond positions according to
- the configuration of X being S, O, or CH;
- or a pharmaceutically acceptable salt thereof.
A compound selected from the group consisting of:
- or a pharmaceutically acceptable salt thereof.
A compound according to Formula (I) comprising:
- or a pharmaceutically acceptable salt thereof.
A compound according to Formula (IA) comprising:
- or a pharmaceutically acceptable salt thereof.
A compound according to Formula (II) comprising:
- or a pharmaceutically acceptable salt thereof.
A compound according to Formula (III) comprising:
- or a pharmaceutically acceptable salt thereof.
A compound according to Formula (IV) comprising:
- or a pharmaceutically acceptable salt thereof.
A compound selected from the group consisting of:
- racemic 1-(2H-1,3-benzoxathiol-5-yl)-N-methylpropan-2-amine;
- (2R)-1-(2H-1,3-benzoxathiol-5-yl)-N-methylpropan-2-amine;
- (2S)-1-(2H-1,3-benzoxathiol-5-yl)-N-methylpropan-2-amine;
- 1-(2H-1,3-benzoxathiol-6-yl)-N-methylpropan-2-amine;
- (2R)-1-(2H-1,3-benzoxathiol-6-yl)-N-methylpropan-2-amine;
- (2S)-1-(2H-1,3-benzoxathiol-6-yl)-N-methylpropan-2-amine;
- 1-(1-benzothiophen-6-yl)-N-methylpropan-2-amine;
- (2R)-1-(1-benzothiophen-6-yl)-N-methylpropan-2-amine;
- (2S)-1-(1-benzothiophen-6-yl)-N-methylpropan-2-amine;
- 1-(1-benzothiophen-5-yl)-N-methylpropan-2-amine;
- (2R)-1-(1-benzothiophen-5-yl)-N-methylpropan-2-amine;
- and (2S)-1-(1-benzothiophen-5-yl)-N-methylpropan-2-amine, or a pharmaceutically acceptable salt, solvate, stereoisomer, tautomer, or prodrug thereof.
A compound or a prodrug, therapeutically active metabolite, hydrate, solvate, or pharmaceutically acceptable salt thereof comprising:
A compound or a prodrug, therapeutically active metabolite, hydrate, solvate, or pharmaceutically acceptable salt thereof comprising:
A compound or a prodrug, therapeutically active metabolite, hydrate, solvate, or pharmaceutically acceptable salt thereof comprising:
A compound or a prodrug, therapeutically active metabolite, hydrate, solvate, or pharmaceutically acceptable salt thereof comprising
A compound or a prodrug, therapeutically active metabolite, hydrate, solvate, or pharmaceutically acceptable salt thereof comprising:
A compound or a prodrug, therapeutically active metabolite, hydrate, solvate, or pharmaceutically acceptable salt thereof comprising:
A compound or a prodrug, therapeutically active metabolite, hydrate, solvate, or pharmaceutically acceptable salt thereof comprising:
A compound or a prodrug, therapeutically active metabolite, hydrate, solvate, or pharmaceutically acceptable salt thereof comprising:
A compound or a prodrug, therapeutically active metabolite, hydrate, solvate, or pharmaceutically acceptable salt thereof comprising:
A compound or a prodrug, therapeutically active metabolite, hydrate, solvate, or pharmaceutically acceptable salt thereof comprising:
The compound of any claim above, wherein the compound comprises a single isolated one enantiomeric form.
The compound of any claim above, wherein the compound comprises a mixture of enantiomeric forms.
The method of any claim above, wherein the compound comprises a single one isolated enantiomeric form.
The compound of any claim above, wherein the compound comprises a mixture of enantiomeric forms.
A method of synthesizing any of the compounds of any of the above claims, comprising performing the synthesis schemes selected from:
- 1, 2A, 3B, 3 and 4.
Dependencies are inferred from the claim text.