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US 8,697,710 B2Granted
Optionally substituted 3-amino-4-(thioxo or imino)-4,5-dihydro-2H-pyrazolo [3,4-d]pyrimidin-6(7H)-ones
AssigneeIntra-Cellular Therapies, Inc.
InventorsPeng Li, Jun Zhao, Hailin Zeng, Lawrence Wennogle
Life of this patent
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Abstract
The present invention relates to optionally substituted 3-amino-4,5-dihydro-(1H or 2H)-pyrazolo[3,4-d]pyrimidin-6(7H)-ones and their 4-imino or 4-thioxo derivatives, e.g., 3-amino-4-(thioxo or imino)-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-6(7H)-ones, 3-amino-4-(thioxo or imino)-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-6(7H)-ones, 3-amino-4-(thioxo or imino)-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6(7H)-ones, processes for their production, their use as pharmaceuticals and pharmaceutical compositions comprising them.
Claims29
A compound of Formula II:
- wherein
- (i) Q is —C(═S)—, —C(═N(R6))— or —C(R14)(R15)—;
- (ii) R1 is H or C1-6alkyl;
- (iii) R2 is
- H,
- C1-6alkyl wherein said alkyl group is optionally substituted with one or more halo or hydroxy,
- (iv) R3 is
- 1) -D-E-F wherein:
- D is a methylene;
- E is
- phenylene or —C6H4—, wherein the phenylene group is optionally substituted with halo,
- F is
- H,
- halo,
- C1-6alkyl,
- haloC1-6alkyl,
- aryl,
- C3-8cycloalkyl optionally containing one or more atom selected from a group consisting of N, S or O, and optionally substituted with one or more C1-6alkyl,
- heteroaryl, wherein said heteroaryl is optionally substituted with one or more C1-6alkyl, halo or haloC1-6alkyl;
- C1-6alkoxy,
- —O-haloC1-6alkyl,
- C1-6alkylsulfonyl,
- —C(O)—R13, wherein R13 is —N(R14)(R15), C1-6alkyl, —OC1-6alkyl, haloC1-6alkyl, aryl, or heteroaryl;
- —N(R14)(R15);
- or
- 2) attached to one of the nitrogens on the pyrazolo portion of Formula II and is a moiety of Formula A
- wherein:
- X, Y and Z are C,
- R8, R9, R11 and R12 are independently H or halogen;
- and
- R10 is
- halogen,
- C1-6alkyl,
- C3-8cycloalkyl,
- heteroC3-8cycloalkyl,
- haloC1-6alkyl,
- aryl or heteroaryl,
- C1-6alkyl sulfonyl,
- arylcarbonyl,
- heteroarylcarbonyl,
- C1-6alkoxycarbonyl,
- Aminocarbonyl,
- —N(R14)(R15);
- wherein said aryl, heteroaryl, cycloalkyl or heterocycloalkyl is optionally substituted with one or more C1-6alkyl, halogen, haloC1-6alkyl, hydroxy, carboxy, —SH or an additional aryl or heteroaryl;
- (v) R4 and R5 are independently:
- H,
- phenyl wherein said phenyl is optionally substituted with one or more halo, hydroxy, C1-6alkyl, C1-6alkoxy or another aryl group;
- (vi) R6 is H, C1-6alkyl or C3-8cycloalkyl;
- (vii) R14 and R15 are independently H or C1-6alkyl, in free or salt form.
46 more elements
Dependencies are inferred from the claim text.