Acid addition salts of piperazine derivatives
AssigneeAsceneuron SA
InventorsAnna QUATTROPANI, Santosh S. KULKARNI, Awadut Gajendra GIRI, Dawn V. TORONTO, David Malcolm CROWE
Life of this patent
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Abstract
The invention relates to acid addition salts of piperazine derivatives, as well as solid forms, such as polymorphic forms, thereof, which are useful as pharmaceutical ingredients and, in particular, as glycosidase inhibitors.
Claims19
-14. (canceled)
An acid addition salt of hydrochloric acid, maleic acid, tartaric acid, sulfuric acid or p-toluolsulfonic acid with compounds of formula I
- wherein:
- X denotes O or CH2;
- n denotes 0 or 1;
- and
- Q denotes one of the following groups:
- Z1 is S, O, NR3;
- Z2, Z2′, Z3 independently denote CR5, CR6 or N;
- R5, R5′, R6, R7 independently denote H, Hal, NR3R4, NO2, straight chain or branched alkyl having 1 to 12 carbon atoms, wherein 1 to 3 CH2-groups may be replaced by a group selected from O, NR3, S, SO, SO2, CO, COO, OCO, CONR3, NR3CO and wherein 1 to 5 hydrogen atoms may be replaced by Hal, NR3R4, NO2, OR3, Het, Ar, Cyc, or denote Ar, Het or Cyc;
- R8 denotes H, methyl or straight chain or branched alkyl having 2 to 12 carbon atoms, wherein 1 to 3 CH2-groups may be replaced by a group selected from O, NR3, S, SO, SO2, CO, COO, OCO, CONR3, NR3CO and wherein 1 to 5 hydrogen atoms may be replaced by Hal, NR3R4 or NO2;
- R3, R4 denote each independently H or a straight chain or branched alkyl group having 1 to 12 carbon atoms;
- Hal denotes F, Cl, Br or I;
- Het denotes a saturated, unsaturated or aromatic ring, being monocyclic or bicyclic or fused-bicyclic and having 3- to 8-members and containing 1 to 4 heteroatoms selected from N, O and S, which may be substituted by 1 to 3 substituents selected from R5, Hal and OR3;
- Ar denotes a 6-membered carbocyclic aromatic ring or a fused or non-fused bicyclic aromatic ring system, which is optionally substituted by 1 to 3 substituents independently selected from R5, OR3 and Hal;
- Cyc denotes a saturated or an unsaturated carbocyclic ring having from 3 to 8 carbon atoms which is optionally substituted by 1 to 3 substituents independently selected from R5 or Hal or OH;
- as well as solid forms thereof.
N-(5-{4-[(1S)-1-(2H-1,3-benzodioxol-5-yl)ethyl]piperazin-1-yl}-1,3,4-thiadiazol-2-yl)acetamide, mono-hydrochloride in a solid form having the characteristic X-ray powder diffraction pattern as shown on FIG. 11.
Dependencies are inferred from the claim text.