# US 2013/0158094 A1 · Fused tricyclic ether carbamates and their use > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2013/0158094 A1 - Document ID: US20130158094A1 - Status: Published application - Kind: A1 - Application number: 13/819,141 - Filed: 2011-09-02 - Published: 2013-06-20 - Earliest claimed: 2010-09-02 - Assignees: Purdue Research Foundation - Inventors: Arun K. Ghosh; Chun-Xiao Xu; Hiroaki Mitsuya; Garth Parham - Web page: https://patentgrep.com/patent/US20130158094A1 ## CPC - C07D 495/14: Ortho-condensed systems - A61P 31/18: for HIV - C07D 493/04: Ortho-condensed systems - C07D 493/14: Ortho-condensed systems - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS ## Abstract Tricylic ether carbamates that inhibit HIV proteolytic enzymes and processes for preparing the compounds are describes. Methods of using the disclosed compounds for treating patients infected with HIV are also described. ## Claims ### Claim 1 A compound of the formula or a pharmaceutically acceptable salt thereof, wherein X1 is a bond or optionally substituted alkylene; X2 is a bond, C(O), S(O), S(O)2, optionally substituted amino, or optionally substituted alkylene; R1 and R2 are in each instance independently selected from the group consisting of hydrogen, P(O)(OR)2, and a prodrug forming group, where R is independently selected in each instance from hydrogen or alkyl; R3 is sulfonyl, acyl, amino, alkyl, heteroalkyl, cycloalkyl, cycloheteroalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl, each of which is optionally substituted; R4 is hydrogen, halogen, —OH, or —NO2, or R4 is amino, alkoxyl, sulfonyl, acyl, alkyl, heteroalkyl, cycloalkyl, cycloheteroalkyl, aryl, and heteroaryl, each of which is optionally substituted; or R3, R4, X2 and the attached nitrogen form an optionally substituted heterocyclyl; R5 and R6 are independently in each instance hydrogen or selected from the group consisting of alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, arylalkyl, heteroaryl, and heteroarylalkyl, each of which is optionally substituted; Z is wherein * indicates the point of attachment; m is 0, 1, or 2; W1 and W2 are in each instance independently selected from the group consisting of optionally substituted alkylene, alkyleneoxy, alkyleneamino, alkylenethio, alkylenesulfoxyl, and alkylenesulfonyl; W3 and W4 are in each instance independently selected from the group consisting of amino, oxygen, alkylene, alkyleneoxy, alkyleneamino, and heteroalkylene, wherein at least one of W1 or W2 is oxygen, and wherein when one of W1 or W2 is optionally substituted methylene, at least one of W3 or W4 is oxygen or alkyleneoxy, and wherein Z does not include a peroxide bond, a sulfenate bond, or a sulfenamide bond; X3 is a bond or optionally substituted methylene; and Y is hydrogen, hydroxyl, or carbonyl, or amino, acyl, sulfonyl, alkyl, or heteroalkyl, each of which is optionally substituted is described; or Z is wherein * indicates the point of attachment; n is 1, 2, or 3; W1 and W2 are in each instance independently selected from the group consisting of optionally substituted methylene, oxygen, and amino; W3 and W4 are in each instance independently selected from the group consisting of amino, oxygen, alkylene, and heteroalkylene, wherein at least one of W1 or W2 is oxygen, and wherein when one of W1 or W2 is optionally substituted methylene, at least one of W3 or W4 is oxygen, and wherein Z does not include a peroxide bond, a sulfenate bond, or a sulfenamide bond; X3 is a bond or optionally substituted methylene; and Y is hydrogen, hydroxyl, or carbonyl, or amino, acyl, sulfonyl, alkyl, or heteroalkyl, each of which is optionally substituted. ### Claim 2 (canceled) ### Claim 3 (depends on 1) The compound of claim 1 wherein Z is wherein * indicates the point of attachment. ### Claim 4 (canceled) ### Claim 5 (depends on 1) The compound of claim 1 wherein X3 is a bond. ### Claim 6 (depends on 1) The compound of claim 1 wherein Z is n is 1 or 2, and W4 is optionally substituted ethylene or propylene. ### Claim 7 (canceled) ### Claim 8 (depends on 1) The compound of claim 1 wherein Z is n is 1, and W4 is optionally substituted ethylene. ### Claim 9 (canceled) ### Claim 10 (depends on 1) The compound of claim 1 wherein Y is hydrogen. ### Claim 11 (depends on 1) The compound of claim 1 wherein W1, W2, and W3 are oxygen. ### Claim 12 (depends on 1) The compound of claim 1 wherein Z is ### Claim 13 (depends on 1) The compound of claim 1 wherein Z is ### Claim 14 (depends on 1) The compound of claim 1 wherein R1 and R2 are each hydrogen. ### Claim 15 (depends on 1) The compound of claim 1 wherein R5 is optionally substituted arylalkyl, X1 is a bond, R6 is hydrogen, X2 is S(O)2, R4 is optionally substituted aryl, and R3 is iso-butyl. ### Claim 16 (canceled) ### Claim 17 (canceled) ### Claim 18 (canceled) ### Claim 19 (canceled) ### Claim 20 (canceled) ### Claim 21 (depends on 1) The compound of claim 1 wherein R3 is optionally substituted arylalkyl. ### Claim 22 (depends on 1) The compound of claim 1 wherein W2 is oxygen. ### Claim 23 (depends on 1) The compound of claim 1 wherein W3 or W4 is oxygen. ### Claim 24 (depends on 1) The compound of claim 1 wherein W2 and one of W3 or W4 is oxygen. ### Claim 25 (depends on 1) The compound of claim 1 wherein W2 and W3 are oxygen. ### Claim 26 (depends on 1) The compound of claim 1 wherein each of W1, W2, and W3 is oxygen. ### Claim 27 (depends on 1) The compound of claim 1 wherein W1 is optionally substituted methylene. ### Claim 28 (canceled) ### Claim 29 (depends on 1) A pharmaceutical composition comprising one or more compounds of claim 1 and further comprising one or more carriers, diluents, or excipients, or a combination thereof for treating HIV infection. ### Claim 30 (canceled) ### Claim 31 (depends on 1) A method for treating a patient in need of relieve of an HIV infection, the method comprising the step of administering to a patient in need of relief from the HIV infection a therapeutically effective amount of one or more compounds of claim 1 or a pharmaceutical composition thereof.