# US 10,865,208 B2 · ATG7 inhibitors and the uses thereof

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- Number: US 10,865,208 B2
- Document ID: US10865208B2
- Status: Granted
- Kind: B2
- Application number: 16/348,940
- Filed: 2017-11-10
- Published: 2019-12-19
- Granted: 2020-12-15
- Earliest claimed: 2016-11-11
- Assignees: Millennium Pharmaceuticals, Inc.
- Applicants: Millennium Pharmaceuticals, Inc.
- Inventors: Sharmila Adhikari; Emily Frances Calderwood; Dylan Bradley England; Alexandra E. Gould; Sean J. Harrison; Shih-Chung Huang; Liting Ma
- Web page: https://patentgrep.com/patent/US10865208B2

## CPC

- C07D 487/04: Ortho-condensed systems
- C07H 19/23: Heterocyclic radicals containing two or more heterocyclic rings condensed among themselves or condensed with a common carbocyclic ring system, not provided for in groups C07H19/14 - C07H19/22
- A61K 31/519: ortho- or peri-condensed with heterocyclic rings
- A61P 35/04: specific for metastasis
- C07D 231/12: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 237/08: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 333/54: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Disclosed are chemical entities which are compounds of formula (I): or a pharmaceutically acceptable salt thereof, wherein R1, R2, and Ra have the values described herein. Chemical entities according to the disclosure can be useful as inhibitors of ATG7. Further provided are pharmaceutical compositions comprising a chemical entity of the disclosure and methods of using the compositions in the treatment of cancer.

## Claims

### Claim 1

A chemical entity which is a compound or a pharmaceutically acceptable salt of formula (I):
wherein:
R1 is H and R2 is H; or R1 is H and R2 is —OH; or R1 is F and R2 is H;
Ra is H, I, —CN, —CO2CH3, —C(O)CH3, —C(S)NH2, —C(O)NH2, —S(O)CH3, C1-3 fluoroaliphatic, —O—C1-3 fluoroaliphatic, —S—C1-3 fluoroaliphatic, -T1-Rb, Rbb, —O-T1-Rb, —O—Rdd, —S-T1-Rc, or —S—Ree;
T1 is absent or C1-C3 alkylene optionally substituted with 1 or 2 independent occurrences of —CH3,
Rb is 3-7 membered cycloaliphatic; 4-10-membered heterocyclyl having 1-4 heteroatoms independently selected from nitrogen, oxygen, and sulfur; 6-10-membered aryl; or 5-10-membered heteroaryl having 1-5 heteroatoms independently selected from nitrogen, oxygen, and sulfur; wherein each Rb is substituted with 0-5 Rd;
Rc is 3-7 membered cycloaliphatic; 4-10-membered heterocyclyl having 1-4 heteroatoms independently selected from nitrogen, oxygen, and sulfur; 6-10-membered aryl; or 5-10-membered heteroaryl having 1-5 heteroatoms independently selected from nitrogen, oxygen, and sulfur; wherein each Rc is substituted with 0-5 Rf;
each occurrence of Rd is independently halo, —OH, —CN, —NO2, C1-4 aliphatic, —O—C1-3 aliphatic, C1-3 fluoroaliphatic, —O—C1-3 fluoroaliphatic, —S—C1-3 aliphatic, —S—C1-3 fluoroaliphatic, —N(Re)2, —C(O)—N(Re)2, —SO2CH3, —S(O)CH3, or —O—CH2-phenyl wherein the phenyl ring is optionally substituted with 1 or 2 independent occurrences of halo, —CN, C1-3 aliphatic, or —O—C1-3 aliphatic; or two occurrences of Rd are taken together to form a 5 or 6 membered cycloaliphatic or heterocyclic ring, having 1-2 heteroatoms independently selected from nitrogen, oxygen, and sulfur, which is further optionally substituted with one occurrence of ═O and optionally substituted with one occurrence of Rg;
each occurrence of Rf is independently halo, —OH, —CN, —NO2, C1-4 aliphatic, —O—C1-3 aliphatic, C1-3 fluoroaliphatic, —O—C1-3 fluoroaliphatic, —S—C1-3 aliphatic, —S—C1-3 fluoroaliphatic, —N(Re)2, —C(O)—N(Re)2, —SO2CH3, —S(O)CH3, or —O—CH2-phenyl wherein the phenyl ring is optionally substituted with 1 or 2 independent occurrences of halo, —CN, C1-3 aliphatic, or —O—C1-3 aliphatic; or two occurrences of Rf are taken together to form a 5 or 6 membered cycloaliphatic or heterocyclic ring, having 1-2 heteroatoms independently selected from nitrogen, oxygen, and sulfur, which is further optionally substituted with one occurrence of ═O and optionally substituted with one occurrence of Rg;
Rbb is C1-3 aliphatic substituted with 0-5 Rbx;
Rdd is C1-3 aliphatic substituted with 0-5 Rdx;
Ree is C1-3 aliphatic substituted with 0-5 Rfx;
each occurrence of Rbx is independently —OH, —CN, —NO2, C1-4 aliphatic, —O—C1-3 aliphatic, C1-3 fluoroaliphatic, —O—C1-3 fluoroaliphatic, —S—C1-3 aliphatic, —S—C1-3 fluoroaliphatic, —N(Re)2, —C(O)—N(Re)2, —SO2CH3, —S(O)CH3, or —O—CH2-phenyl wherein the phenyl ring is optionally substituted with 1 or 2 independent occurrences of halo, —CN, C1-3 aliphatic, or —O—C1-3 aliphatic; or two occurrences of Rbx are taken together to form a 5 or 6 membered cycloaliphatic or heterocyclic ring, having 1-2 heteroatoms independently selected from nitrogen, oxygen, and sulfur, which is further optionally substituted with one occurrence of ═O and optionally substituted with one occurrence of R8;
each occurrence of Rdx is independently —Cl, —OH, —CN, —NO2, C1-4 aliphatic, —O—C1-3 aliphatic, C1-3 fluoroaliphatic, —O—C1-3 fluoroaliphatic, —S—C1-3 aliphatic, —S—C1-3 fluoroaliphatic, —N(Re)2, —C(O)—N(Re)2, —SO2CH3, —S(O)CH3, or —O—CH2-phenyl wherein the phenyl ring is optionally substituted with 1 or 2 independent occurrences of halo, —CN, C1-3 aliphatic, or —O—C1-3 aliphatic; or two occurrences of Rdx are taken together to form a 5 or 6 membered cycloaliphatic or heterocyclic ring, having 1-2 heteroatoms independently selected from nitrogen, oxygen, and sulfur, which is further optionally substituted with one occurrence of ═O and optionally substituted with one occurrence of R8;
each occurrence of Rfx is independently —OH, —CN, —NO2, C1-4 aliphatic, —O—C1-3 aliphatic, C1-3 fluoroaliphatic, —O—C1-3 fluoroaliphatic, —S—C1-3 aliphatic, —S—C1-3 fluoroaliphatic, —N(Re)2, —C(O)—N(Re)2, —SO2CH3, —S(O)CH3, or —O—CH2-phenyl wherein the phenyl ring is optionally substituted with 1 or 2 independent occurrences of halo, —CN, C1-3 aliphatic, or —O—C1-3 aliphatic; or two occurrences of Rfx are taken together to form a 5 or 6 membered cycloaliphatic or heterocyclic ring, having 1-2 heteroatoms independently selected from nitrogen, oxygen, and sulfur, which is further optionally substituted with one occurrence of ═O and optionally substituted with one occurrence of Rg;
Rg is C1-3 aliphatic; and
Re is hydrogen or C1-3 aliphatic.

### Claim 2 (depends on 1)

The chemical entity of claim 1, wherein R1 is H and R2 is H.

### Claim 3 (depends on 1)

The chemical entity of claim 1, wherein Ra is I, C1-3 fluoroaliphatic, —O—C1-3 fluoroaliphatic, —S—C1-3 fluoroaliphatic, -T1-Rb, Rbb, —O-T1-Rb, —O—Rdd, —S-T1-Rc, or —S—Ree.

### Claim 4 (depends on 1)

The chemical entity of claim 1 wherein Ra is —O—C1-3 fluoroaliphatic, or —O—Rdd.

### Claim 5 (depends on 1)

The chemical entity of claim 1 wherein:
Ra is —S—C1-3 fluoroaliphatic, —S-T1-Rc, or —S—Ree;
each occurrence of Rf is independently halo, —OH, —CN, C1-4 aliphatic, —O—C1-3 aliphatic, —O—C1-3 fluoroaliphatic, —N(Re)2, or —C(O)—N(Re)2; or two occurrences of Rf are taken together to form a 5 or 6 membered cycloaliphatic or heterocyclic ring, having 1-2 heteroatoms independently selected from nitrogen, oxygen, and sulfur, which is further optionally substituted with one occurrence of ═O and optionally substituted with one occurrence of Rg; and
each occurrence of Rfx is independently —OH, —CN, C1-4 aliphatic, —O—C1-3 aliphatic, C1-3 fluoroaliphatic, —N(Re)2, or —C(O)—N(Re)2, or 5 or 6 membered cycloaliphatic or heterocyclic ring, having 1-2 heteroatoms independently selected from nitrogen, oxygen, and sulfur, which is further optionally substituted with one occurrence of ═O and optionally substituted with one occurrence of Rg.

### Claim 6 (depends on 1)

The chemical entity of claim 1 which is a compound or a pharmaceutically acceptable salt of formulas (III-a)-(III-d):

### Claim 7 (depends on 6)

The chemical entity of claim 6, wherein Ra is I, —CN, C1-3 fluoroaliphatic, —O—C1-3 fluoroaliphatic, —S—C1-3 fluoroaliphatic, -T1-Rb, Rbb, —O-T1-Rb, —O—Rdd, —S-T1-Rc, or —S—Ree.

### Claim 8 (depends on 7)

The chemical entity of claim 7, wherein Ra is I, —CN, C1-3 fluoroaliphatic, —O—C1-3 fluoroaliphatic, Rbb, or O—Rdd.

### Claim 9 (depends on 7)

The chemical entity of claim 7, wherein:
Ra is —S—C1-3 fluoroaliphatic or —S—Ree;
Ree is C1-3 aliphatic substituted with 0-2 Rfx; and
each occurrence of Rfx is independently —OH, —CN, C1-4 aliphatic, —O—C1-3 aliphatic, C1-3 fluoroaliphatic, —N(Re)2, or —C(O)—N(Re)2.

### Claim 10 (depends on 7)

The chemical entity of claim 7, wherein Ra is -T1-Rb, —O-T1-Rb, or —S-T1-Rc.

### Claim 11 (depends on 10)

The chemical entity of claim 10, wherein:
Ra is -T1-Rb, —O-T1-Rb;
T1 is absent, —CH2— or —CH2CH2—; and
Rb is substituted with 0-2 Rd.

### Claim 12 (depends on 10)

The chemical entity of claim 10, wherein:
Ra is —S-T1-Rc; and
T1 is absent, —CH2— or —CH2CH2—.

### Claim 13 (depends on 12)

The chemical entity of claim 12, wherein:
Rc is 3-7 membered cycloaliphatic or 4-10-membered heterocyclyl having 1-4 heteroatoms independently selected from nitrogen, oxygen, and sulfur;
Rc is substituted with 0-2 Rf;
each occurrence of Rf is independently Rfa; and
Rfa is halo, —OH, —CN, or C1-4 aliphatic.

### Claim 14 (depends on 12)

The chemical entity of claim 12, wherein:
Rc is a 6-10-membered aryl; or 5-10-membered heteroaryl having 1-5 heteroatoms,
Rc is substituted with 0-2 Rf; and
Re is —H, —CH3, or —CH2CH3.

### Claim 15 (depends on 14)

The chemical entity of claim 14, wherein:
two occurrences of Rf are taken together to form a 5 or 6 membered cycloaliphatic or heterocyclic ring, having 1-2 heteroatoms independently selected from nitrogen, oxygen, and sulfur, which is further optionally substituted with one occurrence of ═O and optionally substituted with one occurrence of Rg; and
Rg is methyl.

### Claim 16 (depends on 14)

The chemical entity of claim 14, wherein:
each occurrence of Rf is independently Rfb; and
Rfb is halo, —OH, —CN, C1-4 aliphatic, —O—C1-3 aliphatic, —O—C1-3 fluoroaliphatic, —N(Re)2, or —C(O)—N(Re)2.

### Claim 17 (depends on 14)

The chemical entity of claim 14, wherein Rc is phenyl, pyridyl, furanyl or pyrazolyl optionally substituted by one occurrence of —CH3, —OCH3, or —F, and optionally substituted by one occurrence of —CH3, —OCH3, —F, —Cl, —CF3, or —OCF3.

### Claim 18 (depends on 1)

The chemical entity of claim 1, wherein the chemical entity is selected from the group consisting of:
[(2R,3S,4R,5R)-5-(4-amino-3-methoxy-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-3-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(benzyloxy)methyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-3-ethoxy-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-3-ethyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-3-isopropoxy-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3S,4R,5R)-5-[4-amino-3-(hydroxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-3-ethynyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3S,4R,5R)-5-[4-amino-3-(trifluoromethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2R,3S,4R,5R)-5-[4-amino-3-(3-methoxyprop-1-yn-1-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2R,3S,4R,5R)-5-[4-amino-3-(2-phenylethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-3-cyano-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3S,4R,5R)-5-[4-amino-3-(prop-1-yn-1-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2R,3S,4R,5R)-5-[4-amino-3-(aminomethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-3-carbamoyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3S,4R,5R)-5-[4-amino-3-(3-aminoprop-1-yn-1-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-3-vinyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3S,4R,5R)-5-[4-amino-3-(methoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate
methyl 4-amino-1-{(2R,3R,4S,5R)-3,4-dihydroxy-5-[(sulfamoyloxy)methyl]tetrahydrofuran-2-yl}-1H-pyrazolo[3,4-d]pyrimidine-3-carboxylate;
[(2R,3S,4R,5R)-5-(3-acetyl-4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(1R)-1-methoxyethyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(1S)-1-methoxyethyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(1R)-1-hydroxyethyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(1S)-1-hydroxyethyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(1R)-1-hydroxyethyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(1S)-1-hydroxyethyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3S,4R,5R)-5-[4-amino-3-(2-hydroxypropan-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2R,3S,4R,5R)-5-[4-amino-3-(difluoromethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-3-cyclopropyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3S,4R,5R)-5-[4-amino-3-(difluoromethoxy)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(2-hydroxy-2-methylpropyl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3S,4R,5R)-5-[4-amino-3-(cyanomethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2R,3S,4R,5R)-5-[4-amino-3-(1,3-thiazol-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(3-methylbenzyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-3-{[4-(trifluoromethoxy)benzyl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-3-{[4-(trifluoromethyl)benzyl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(2,4-dichlorophenyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(2-methoxyethyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3S,4R,5R)-5-[4-amino-3-(1H-pyrazol-4-ylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-3-phenoxy-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(4-methoxybenzyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(2-methylbenzyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(3-chlorophenyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(4-methylbenzyl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3S,4R,5R)-5-[4-amino-3-(methylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2R,3S,4R,5R)-5-[4-amino-3-(prop-2-yn-1-ylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(3-fluorobenzyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(pyridin-3-ylmethyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(2-hydroxyethyl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-3-{[(1R,2R)-2-hydroxycyclohexyl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-3-{[(1S,2S)-2-hydroxycyclohexyl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-3-phenyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(cyclopropylmethyl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3S,4R,5R)-5-[4-amino-3-(ethylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2R,3S,4R,5R)-5-[4-amino-3-(benzylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2R,3S,4R,5R)-5-[4-amino-3-(tert-butylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-3-{[(1R,2R)-2-hydroxycyclopentyl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-3-{[(1S,2S)-2-hydroxycyclopentyl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-3-{[(2R)-2-hydroxypropyl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-3-{[(2S)-2-hydroxypropyl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-3-{[(2R)-2-hydroxypropyl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-3-{[(2S)-2-hydroxypropyl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3S,4R,5R)-5-[4-amino-3-(cyclobutylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2R,3S,4R,5R)-5-[4-amino-3-(1,3-oxazol-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2R,3S,4R,5R)-5-[4-amino-3-(isopropylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(pyridin-2-ylmethyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-3-carbamothioyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(1-methyl-1H-pyrazol-4-yl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3S,4R,5R)-5-[4-amino-3-(cyclopentylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(4-fluorobenz yl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(4-chlorophenyl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3S,4R,5R)-5-[4-amino-3-(cyclopropylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2R,3S,4R,5R)-5-[4-amino-3-(pyridin-4-ylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(1-naphthylmethyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3S,4R,5R)-5-[4-amino-3-(1H-pyrazol-5-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(3-methylphenyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-3-{[(1R)-1-phenylethyl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-3-{[(1S)-1-phenylethyl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3S,4R,5R)-5-[3-(allyloxy)-4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2R,3S,4R,5R)-5-[4-amino-3-(azetidin-3-ylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-3-{[(5-chloro-2-furyl)methyl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(2-methylphenyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3S,4R,5R)-5-[4-amino-3-(2-chloroethoxy)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2R,3S,4R,5R)-5-[4-amino-3-(benzyloxy)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2R,3S,4R,5R)-5-[4-amino-3-(isobutylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(2-chlorophenyl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-3-{[2-(dimethylamino)ethyl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(2-methyl-3-furyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3S,4R,5R)-5-[4-amino-3-(phenylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(2,2,2-trifluoroethyl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3S,4R,5R)-5-[4-amino-3-(1-naphthylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(difluoromethyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-3-{[(1-hydroxycyclohexyl)methyl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3S,4R,5R)-5-[4-amino-3-(methylsulfinyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(2-phenylethyl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(4-methylphenyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(cyanomethyl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(cyclohex-1-en-1-ylmethyl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-3-{[(2S,3R)-2-methyltetrahydrofuran-3-yl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-3-{[(2R,3R)-2-methyltetrahydrofuran-3-yl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-3-{[(2R,3S)-2-methyltetrahydrofuran-3-yl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-(4-amino-3-{[(2S,3S)-2-methyltetrahydrofuran-3-yl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,4R,5R)-5-{4-amino-3-[(methylsulfanyl)methyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2S,3S,4R,5R)-5-[4-amino-3-(methylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2S,3S,4R,5R)-5-[4-amino-3-(isopropylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2S,3R,4S,5R)-5-[4-amino-3-(methylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-4-fluoro-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3R,4S,5R)-5-(4-amino-3-{[(3,3-difluorocyclobutyl)methyl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(difluoromethyl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3R,4S,5R)-5-[4-amino-3-(difluoromethoxy)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-4-fluoro-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(2-methyl-3-furyl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-(4-amino-3-{[(2R)-1,1,1-trifluoropropan-2-yl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-(4-amino-3-{[(2S)-1,1,1-trifluoropropan-2-yl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(6-methylpyridin-2-yl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3R,4S,5R)-5-[4-amino-3-(cyclopentylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-4-fluoro-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3R,4S,5R)-5-(4-amino-3-{[2-(diethylamino)ethyl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-(4-amino-3-methoxy-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(3-chlorophenyl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(6-methoxypyridin-2-yl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-(4-amino-3-cyclopropyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(2-fluorophenyl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(2,5-dimethyl-3-furyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(5-nitropyridin-2-yl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-(4-amino-3-{[(1-methyl-1H-imidazol-2-yl)methyl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3R,4S,5R)-5-[4-amino-3-(pyridin-2-ylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-4-fluoro-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(4-methylpyridin-2-yl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3R,4S,5R)-5-[4-amino-3-(methylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-4-fluoro-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(3-fluorophenyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-(4-amino-3-{[4-(trifluoromethyl)pyridin-2-yl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3R,4S,5R)-5-[4-amino-3-(tert-butylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-4-fluoro-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(pyridin-2-ylmethyl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3R,4S,5R)-5-[4-amino-3-(pentan-3-ylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-4-fluoro-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(pyridin-3-ylmethyl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3R,4S,5R)-5-[4-amino-3-(cyclohexylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-4-fluoro-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(3R)-tetrahydrofuran-3-ylsulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(3S)-tetrahydrofuran-3-ylsulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(pyridin-4-ylmethyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(1-methyl-1H-imidazol-2-yl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(4-fluorophenyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(pyridazin-3-ylmethyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(pyridazin-4-ylmethyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-(4-amino-3-{[(2R)-3-methylbutan-2-yl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-(4-amino-3-{[(2S)-3-methylbutan-2-yl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(4-cyanopyridin-2-yl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3R,4S,5R)-5-[4-amino-3-({[(1R)-2,2-difluorocyclopropyl]methyl}sulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-4-fluoro-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2R,3R,4S,5R)-5-[4-amino-3-({[(1S)-2,2-difluorocyclopropyl]methyl}sulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-4-fluoro-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3R,4S,5R)-5-(4-amino-3-{[4-(trifluoromethyl)phenyl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(4-chlorophenyl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(1-methyl-1H-imidazol-5-yl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(cyclopropylmethyl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(2R)-butan-2-ylsulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(2S)-butan-2-ylsulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(2R)-butan-2-ylsulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(2S)-butan-2-ylsulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(2R)-butan-2-ylsulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(2S)-butan-2-ylsulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(1-methyl-1H-imidazol-4-yl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3R,4S,5R)-5-[4-amino-3-(pyridin-3-ylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-4-fluoro-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2R,3R,4S,5R)-5-[4-amino-3-(isopropylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-4-fluoro-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2R,3R,4S,5R)-5-[4-amino-3-({[(1R,2R)-2-methylcyclopropyl]methyl}sulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-4-fluoro-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2R,3R,4S,5R)-5-[4-amino-3-({[(1S,2R)-2-methylcyclopropyl]methyl}sulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-4-fluoro-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2R,3R,4S,5R)-5-[4-amino-3-({[(1R,2S)-2-methylcyclopropyl]methyl}sulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-4-fluoro-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2R,3R,4S,5R)-5-[4-amino-3-({[(15,25)-2-methylcyclopropyl]methyl}sulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-4-fluoro-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(3-methylphenyl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(trifluoromethyl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-(4-amino-3-{[5-(trifluoromethyl)pyridin-2-yl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-(4-amino-3-{[(2R)-1-hydroxypropan-2-yl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-(4-amino-3-{[(2S)-1-hydroxypropan-2-yl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-(4-amino-3-{R 1-methyl-1H-pyrazol-4-yl)methyl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(5-chloropyridin-2-yl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3R,4S,5R)-5-[4-amino-3-(cyclobutylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-4-fluoro-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(cyclobutylmethyl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-(4-amino-3-{[(1R)-1-cyanoethyl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-(4-amino-3-{[(1S)-1-cyanoethyl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3R,4S,5R)-5-[4-amino-3-(pyridin-4-ylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-4-fluoro-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(2-hydroxyethyl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(5-methylpyridin-2-yl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(3-cyanophenyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-{4-amino-3-[(2-methoxyethyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3R,4S,5R)-5-[4-amino-3-(benzylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-4-fluoro-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2R,3R,4S,5R)-5-[4-amino-3-([1,2,4]triazolo[4,3-a]pyridin-3-ylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-4-fluoro-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3R,4S,5R)-5-(4-amino-3-{[(1R)-1-cyclopropylethyl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-(4-amino-3-{[(1S)-1-cyclopropylethyl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3R,4S,5R)-5-(4-amino-3-{[3-(trifluoromethyl)phenyl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,5R)-5-{4-amino-3-[(2-amino-2-oxoethyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3S,5R)-5-[4-amino-3-(2,3-dihydro-1H-inden-5-ylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3S,5R)-5-{4-amino-3-[(2-fluoro-4-methylphenyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,5R)-5-{4-amino-3-[(2-hydroxyethyl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,5R)-5-{4-amino-3-[(4-tert-butylphenyl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3S,5R)-5-[4-amino-3-(cyclobutylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3S,5R)-5-{4-amino-3-[(2,2-difluoroethyl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3S,5R)-5-[4-amino-3-(2-naphthylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2R,3S,5R)-5-[4-amino-3-(cyclopropylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2R,3S,5R)-5-[4-amino-3-(2,3-dihydro-1-benzofuran-6-ylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3S,5R)-5-{4-amino-3-[(difluoromethyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3S,5R)-5-[4-amino-3-(1H-indol-3-ylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2R,3S,5R)-5-[4-amino-3-(trifluoromethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2R,3S,5R)-5-[4-amino-3-(ethylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3S,5R)-5-{4-amino-3-[(2-fluoro-5-methoxyphenyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3S,5R)-5-[4-amino-3-(1,3-thiazol-2-ylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2R,3S,5R)-5-[4-amino-3-(1,3-benzodioxol-5-ylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3S,5R)-5-{4-amino-3-[(2-methylphenyl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3S,5R)-5-[4-amino-3-(tert-butylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3S,5R)-5-{4-amino-3-[(2-fluoro-4-methoxyphenyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,5R)-5-{4-amino-3-[(3-chlorophenyl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,5R)-5-(4-amino-3-{[2-(dimethylamino)-2-oxoethyl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3S,5R)-5-[4-amino-3-(isopropylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3S,5R)-5-{4-amino-3-[(2-fluorophenyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3S,5R)-5-[4-amino-3-(quinolin-2-ylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3S,5R)-5-{4-amino-3-[(4-isopropoxyphenyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,5R)-5-{4-amino-3-[(1-methyl-2-oxo-2,3-dihydro-1H-indol-5-yl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3S,5R)-5-[4-amino-3-(2,3-dihydro-1-benzofuran-5-ylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3S,5R)-5-{4-amino-3-[(4-fluorophenyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,5R)-5-{4-amino-3-[(cyanomethyl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,5R)-5-{4-amino-3-[(5-chloropyridin-2-yl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,5R)-5-(4-amino-3-methoxy-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,5R)-5-{4-amino-3-[(2-fluoro-5-methylphenyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,5R)-5-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,5R)-5-{4-amino-3-[(4-methylphenyl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3S,5R)-5-[4-amino-3-(pyridin-2-ylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2R,3S,5R)-5-[4-amino-3-(difluoromethoxy)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3S,5R)-5-{4-amino-3-[(3,4-dimethylphenyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,5R)-5-(4-amino-3-{[4-(trifluoromethoxy)phenyl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,5R)-5-(4-amino-3-{[3-(trifluoromethoxy)phenyl]sulfanyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,5R)-5-{4-amino-3-[(3-methoxyphenyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2R,3S,5R)-5-[4-amino-3-(methylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2R,3S,5R)-5-[4-amino-3-(2,3-dihydro-1,4-benzodioxin-6-ylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2R,3S,5R)-5-{4-amino-3-[(cyclopropylmethyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,5R)-5-{4-amino-3-[(6-fluoro-2,3-dihydro-1H-inden-5-yl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,5R)-5-{4-amino-3-[(1-benzothiophen-2-ylmethyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,5R)-5-{4-amino-3-[(3-methylphenyl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,5R)-5-{4-amino-3-[(3-fluorophenyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,5R)-5-{4-amino-3-[(3,4-dimethoxyphenyl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2R,3S,5R)-5-{4-amino-3-[(4-methyl-1,3-thiazol-2-yl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2S,3S,5R)-5-[4-amino-3-(trifluoromethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2S,3S,5R)-5-[4-amino-3-(2-naphthylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2S,3S,5R)-5-{4-amino-3-[(2-fluoro-4-methylphenyl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2S,3S,5R)-5-(4-amino-3-ethyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2S,3S,5R)-5-[4-amino-3-(ethylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2S,3S,5R)-5-{4-amino-3-[(4-methylphenyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2S,3S,5R)-5-{4-amino-3-[(2-fluorophenyl)sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2S,3S,5R)-5-[4-amino-3-(2,3-dihydro-1H-inden-5-ylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2S,3S,5R)-5-[4-amino-3-(difluoromethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2S,3S,5R)-5-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
{(2S,3S,5R)-5-[4-amino-3-(methylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2S,3S,5R)-5-[4-amino-3-(isopropylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
{(2S,3S,5R)-5-[4-amino-3-(benzylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate;
[(2S,3S,5R)-5-{4-amino-3-[(5-chloropyridin-2-yl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2S,3S,5R)-5-{4-amino-3-[(4-fluorophenyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2S,3S,5R)-5-{4-amino-3-[(3-chlorophenyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2S,3S,5R)-5-(4-amino-3-methoxy-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate;
[(2S,3S,5R)-5-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate; and
[(2S,3S,5R)-5-{4-amino-3-[(2,2-difluoroethyl) sulfanyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3-hydroxytetrahydrofuran-2-yl]methyl sulfamate, or a pharmaceutically acceptable salt thereof.

### Claim 19 (depends on 1)

A pharmaceutical composition comprising a chemical entity of claim 1, and a pharmaceutically acceptable carrier.