# US 2013/0158052 A1 · Pyrimidine classical cannabinoid compounds and related methods of use

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- Number: US 2013/0158052 A1
- Document ID: US20130158052A1
- Status: Published application
- Kind: A1
- Application number: 13/692,719
- Filed: 2012-12-03
- Published: 2013-06-20
- Earliest claimed: 2008-05-19
- Inventors: Bob M. Moore, II; Steven Gurley; Suni Mustafa; Patrick Allison
- Web page: https://patentgrep.com/patent/US20130158052A1

## CPC

- C07D 491/052: the oxygen-containing ring being six-membered
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 21/02: Muscle relaxants, e.g. for tetanus or cramps
- A61P 27/06: Antiglaucoma agents or miotics
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 35/00: Antineoplastic agents
- C07D 491/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Disclosed are compounds of the formula I: wherein R1, R2, V, W, X, Y and Z are as defined herein. The compounds can be used in the treatment of disorders mediated by the cannabinoid receptors, such as, for example, inflammation.

## Claims

### Claim 1

A method of treating cancer mediated by a cannabinoid receptor comprising contacting said receptor with a compound in an amount to treat said cannabinoid receptor-mediated disorder, wherein the compound is of the formula
wherein
represents an optional double bond wherein the ring that optionally contains it is selected from hexahydro, 6a,10a-dehydro, 8,9-dehydro, and 9,10-dehydro;
----- Y is selected from S, O, CH2, CH(CH3), CH(OH), C(CH3)(OH), C(CH3)2, C(—U(CH2)nU—), C(O), NH, S(O), and S(O)2;
n is an integer ≧1;
U is selected from CH2, S, and O;
Z is selected from H, substituted and unsubstituted alkyl, and
cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocycloalkyl, and heterocycloalkylalkyl, wherein each alkyl portion is optionally substituted and the ring portion of each is optionally substituted with one, two, three, four or five substituents; and
R1 is selected from H and substituted and unsubstituted alkyl.

### Claim 2 (depends on 1)

A method according to claim 1 wherein
R1 is selected from H and alkyl;
Y is selected from carbonyl, dimethylmethylene and hydroxymethylene; and
Z is selected from substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted phenyl, and substituted or unsubstituted thiophenyl.

### Claim 3 (depends on 2)

A method according to claim 2 wherein Z is alkyl, cycloalkyl, phenyl or thiophenyl.

### Claim 4 (depends on 3)

A method according to claim 3 wherein Z is hexyl, cyclohexyl, phenyl or thiophenyl.

### Claim 5 (depends on 2)

A method according to claim 2 wherein Y is dimethylmethylene.

### Claim 6 (depends on 2)

A method according to claim 2 wherein the ring having ----- is hexahydro or 6a,10a-dehydro.

### Claim 7 (depends on 1)

A method according to claim 1 wherein the compound is selected from
a) 3-Benzyl-6,6,9-trimethyl-6a,7,8,9,10,10a-hexahydro-6H-isochromeno[3,4-d]pyrimidin-1-ol;
b) (6aS,9R,10aR)-6,6,9-Trimethyl-3-(2-methyloctan-2-yl)-6a,7,8,9,10,10a-hexahydro-6H-isochromeno[3,4-d]pyrimidin-1-ol;
c) (6aS,9R,10aR)-6,6,9-trimethyl-3-(2-phenylpropan-2-yl)-6a,7,8,9,10,10a-hexahydro-6H-isochromeno[3,4-d]pyrimidin-1-ol;
d) (6aS,9R,10aR)-3-(2-Cyclohexylpropan-2-yl)-6,6,9-trimethyl-6a,7,8,9,10,10a-hexahydro-6H-isochromeno[3,4-d]pyrimidin-1-ol;
e) (6aS,9R,10aR)-6,6,9-Trimethyl-3-(2-(thiophen-2-yl)propan-2-yl)-6a,7,8,9,10,10a-hexahydro-6H-isochromeno[3,4-d]pyrimidin-1-ol;
f) (6aR,9S,10aS)-6,6,9-Trimethyl-3-(2-phenylpropan-2-yl)-6a,7,8,9,10,10a-hexahydro-6H-isochromeno[3,4-d]pyrimidin-1-ol;
g) 3-Benzyl-6,6,9-trimethyl-tetrahydro-6H-isochromeno[3,4-d]pyrimidin-1-ol; and
h) 3-Benzyl-6,6,9-trimethyl-7,8,9,10-tetrahydro-6H-isochromeno[3,4-d]pyrimidin-1-ol.

### Claim 8 (depends on 1)

A method according to claim 1 wherein the cannabinoid receptor is selected from CB-1 and CB-2.