# US 2010/0168176 A1 · Novel compounds, pharmaceutical compositions containing same, and methods of use for same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2010/0168176 A1 - Document ID: US20100168176A1 - Status: Published application - Kind: A1 - Application number: 12/513,888 - Filed: 2007-11-08 - Published: 2010-07-01 - Earliest claimed: 2006-11-08 - Assignees: FASgen, Inc.; The Johns Hopkins University - Inventors: Craig Townsend; Francis Kuhajda; Kandasamy Subburaj; Jill Marie Sturdivant - Web page: https://patentgrep.com/patent/US20100168176A1 ## CPC - C07D 409/12: linked by a chain containing hetero atoms as chain links - A61P 3/04: Anorexiants; Antiobesity agents - A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics - A61P 31/04: Antibacterial agents - A61P 35/00: Antineoplastic agents - A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 - C07D 333/32: Oxygen atoms - C07D 417/12: linked by a chain containing hetero atoms as chain links - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS ## Abstract Compounds having the following general formula, pharmaceutical compositions comprising the compounds, and methods of treating cancer, obesity, and microbial infections using such compositions: wherein: R1=H, C1-C20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl, cyanomethyl, —OCH3, OC(O)CH3 or OC(O)CF3 R2=-OCH2C(O)NHNH—R5, where R5 is (a) phenyl, optionally substituted with one or more of halogen, C1-C8 alkyl, optionally substituted with halogen, —OH, —OR6, where R6 is C1-C8 alkyl, optionally substituted with halogen, or (b) 2-, 3-, or 4-pyridyl, optionally substituted with halogen, —OH, —OR6, where R6 is C1-C8 alkyl, optionally substituted with halogen, or (c) a heterocycle selected from the group consisting of imidazole, thiazole, benzimidazole, benzoxazole, benzthiazole, tetrazole, triazole, and aminothiazole; or (d) —C(O)R7, where R7 is a C1-C20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl, or a heterocycle selected from the group consisting of pyridyl, imidazole, thiazole, benzimidizole, benzoxazole, benzthiazole, tetrazole, triazole, and aminothiazole; and R3 and R4, the same or different from each other, are C1-C20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl. ## Claims ### Claim at position 1 1-25. (canceled) ### Claim 26 A compound of formula: wherein: R1 is selected from the group consisting of H, C1-C20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, alkylaryl, —OCH3, —OC(O)CH3 and —OC(O)CF3; R2 is —OCH2C(O)NHNH—R5, wherein R5 is selected from the group consisting of (a) a phenyl group, optionally substituted with one or more of a halogen or a C1-C8 alkyl, which is optionally substituted with one or more of a first substitution group selected from the group consisting of a halogen, —OH, and —OR6, wherein R6 is C1-C8 alkyl, optionally substituted with one or more halogens; (b) a 2-, 3-, or 4-pyridyl, optionally substituted with one or more of a second substitution group selected from the group consisting of a halogen, —OH, and —OR6, where R6 is C1-C8 alkyl, optionally substituted with one or more halogens; (c) a heterocycle selected from the group consisting of imidazole, thiazole, benzimidizole, benzoxazole, benzthiazole, tetrazole, triazole, and aminothiazole; and (d) −C(O)R7, where R7 is selected from the group consisting of a C1-C20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, alkylaryl, and heterocycle, which is selected from the group consisting of pyridyl, imidazole, thiazole, benzimidizole, benzoxazole, benzthiazole, tetrazole, triazole, and aminothiazole; and R3 and R4 are independently selected from the group consisting of C1-C20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, and alkylaryl; with the proviso that when R1 is —H, —OCH3, or —OC(O)CF3 and R3 is —(CH2)7CH3, then R2 is not —OCH2C(O)NHNH—R5, where R5 is -p-C6H4Cl, —C(O)CH3, or ### Claim 27 (depends on 26) A compound according to claim 26, wherein R1 is H. ### Claim 28 (depends on 26) A compound according to claim 26, wherein R5 is selected from the group consisting of C1-C10 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, and alkylaryl. ### Claim 29 (depends on 26) A compound according to claim 26, wherein R3 is —H or —CH3. ### Claim 30 (depends on 26) A compound according to claim 26, wherein R4 is n-C6-C8 alkyl. ### Claim 31 (depends on 26) A compound according to claim 26, wherein the compound is selected from the group consisting of ### Claim 32 A pharmaceutical composition comprising a pharmaceutical diluent and a compound of formula I: wherein: R1 is selected from the group consisting of H, C1-C20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, alkylaryl, —OCH3, —OC(O)CH3 and —OC(O)CF3; R2 is —OCH2C(O)NHNH—R5, wherein R5 is selected from the group consisting of (a) a phenyl group, optionally substituted with one or more of a halogen or a C1-C8 alkyl, which is optionally substituted with one or more of a first substitution group selected from the group consisting of a halogen, —OH, and —OR6, wherein R6 is C1-C8 alkyl, optionally substituted with one or more halogens; (b) a 2-, 3-, or 4-pyridyl, optionally substituted with one or more of a second substitution group selected from the group consisting of a halogen, —OH, and —OR6, where R6 is C1-C8 alkyl, optionally substituted with one or more halogens; (c) a heterocycle selected from the group consisting of imidazole, thiazole, benzimidizole, benzoxazole, benzthiazole, tetrazole, triazole, and aminothiazole; and (d) —C(O)R7, where R7 is selected from the group consisting of a C1-C20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, alkylaryl, and heterocycle, which is selected from the group consisting of pyridyl, imidazole, thiazole, benzimidizole, benzoxazole, benzthiazole, tetrazole, triazole, and aminothiazole; and R3 and R4 are independently selected from the group consisting of C1-C20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, and alkylaryl; with the proviso that when R1 is —H, —OCH3, or —OC(O)CF3 and R3 is —(CH2)7CH3, then R2 is not —OCH2C(O)NHNH—R5, where R5 is -p-C6H4Cl, —C(O)CH3, or ### Claim 33 (depends on 32) A pharmaceutical composition according to claim 32, wherein R1 is H. ### Claim 34 (depends on 32) A pharmaceutical composition according to claim 32, wherein R5 is selected from the group consisting of C1-C10 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, and alkylaryl. ### Claim 35 (depends on 32) A pharmaceutical composition according to claim 32, wherein R3 is —H or —CH3. ### Claim 36 (depends on 32) A pharmaceutical composition according to claim 32, wherein R4 is n-C6-C8 alkyl. ### Claim 37 (depends on 32) A pharmaceutical composition according to claim 32, wherein the compound is selected from the group consisting of: ### Claim 38 A method of treating cancer in a subject, comprising administering an effective amount of a pharmaceutical composition comprising a pharmaceutical diluent and a compound of formula I: wherein: R1 is selected from the group consisting of H, C1-C20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, alkylaryl, —OCH3, —OC(O)CH3 and —OC(O)CF3; R2 is —OCH2C(O)NHNH—R5, wherein R5 is selected from the group consisting of (a) a phenyl group, optionally substituted with one or more of a halogen or a C1-C8 alkyl, which is optionally substituted with one or more of a first substitution group selected from the group consisting of a halogen, —OH, and —OR6, wherein R6 is C1-C8 alkyl, optionally substituted with one or more halogens; (b) a 2-, 3-, or 4-pyridyl, optionally substituted with one or more of a second substitution group selected from the group consisting of a halogen, —OH, and —OR6, where R6 is C1-C8 alkyl, optionally substituted with one or more halogens; (c) a heterocycle selected from the group consisting of imidazole, thiazole, benzimidizole, benzoxazole, benzthiazole, tetrazole, triazole, and aminothiazole; and (d) —C(O)R7, where R7 is selected from the group consisting of a C1-C20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, alkylaryl, and heterocycle, which is selected from the group consisting of pyridyl, imidazole, thiazole, benzimidizole, benzoxazole, benzthiazole, tetrazole, triazole, and aminothiazole; and R3 and R4 and independently selected from the group consisting of C1-C20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, and alkylaryl; with the proviso that when R1 is —H, —OCH3, or —OC(O)CF3 and R3 is —(CH2)7CH3, then R2 is not —OCH2C(O)NHNH—R5, where R5 is -p-C6H4Cl, —C(O)CH3, or ### Claim 39 (depends on 38) The method of claim 38, wherein the subject is a human. ### Claim 40 (depends on 39) The method of claim 39 wherein the pharmaceutical composition comprises a compound selected from the group consisting of: ### Claim 41 (depends on 38) The method of claim 38, wherein the subject is an animal. ### Claim 42 (depends on 41) The method of claim 41, wherein the pharmaceutical composition comprises a compound selected from the group consisting of: ### Claim 43 A method of inhibiting fatty acid synthase activity in a subject comprising administering an effective amount of a pharmaceutical composition comprising a pharmaceutical diluent and a compound of formula I: wherein: R1 is selected from the group consisting of H, C1-C20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, alkylaryl, —OCH3, —OC(O)CH3 and —OC(O)CF3; R2 is —OCH2C(O)NHNH—R5, wherein R5 is selected from the group consisting of (a) a phenyl group, optionally substituted with one or more of a halogen or a C1-C8 alkyl, which is optionally substituted with one or more of a first substitution group selected from the group consisting of a halogen, —OH, and —OR6, wherein R6 is C1-C8 alkyl, optionally substituted with one or more halogens; (b) a 2-, 3-, or 4-pyridyl, optionally substituted with one or more of a second substitution group selected from the group consisting of a halogen, —OH, and —OR6, where R6 is C1-C8 alkyl, optionally substituted with one or more halogens; (c) a heterocycle selected from the group consisting of imidazole, thiazole, benzimidizole, benzoxazole, benzthiazole, tetrazole, triazole, and aminothiazole; and (d) —C(O)R7, where R7 is selected from the group consisting of a C1-C20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, alkylaryl, and heterocycle, which is selected from the group consisting of pyridyl, imidazole, thiazole, benzimidizole, benzoxazole, benzthiazole, tetrazole, triazole, and aminothiazole; and R3 and R4 and independently selected from the group consisting of C1-C20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, and alkylaryl; with the proviso that when R1 is —H, —OCH3, or —OC(O)CF3 and R3 is —(CH2)7CH3, then R2 is not —OCH2C(O)NHNH—R5, where R5 is -p-C6H4Cl, —C(O)CH3, or ### Claim 44 (depends on 43) The method of claim 43, wherein the subject is a human. ### Claim 45 (depends on 43) The method of claim 43, wherein the subject is an animal. ### Claim 46 A method of inhibiting growth of invasive microbial cells in a subject comprising the administration of an effective amount of a pharmaceutical composition comprising a pharmaceutical diluent and a compound of formula I: wherein: R1 is selected from the group consisting of H, C1-C20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, alkylaryl, —OCH3, —OC(O)CH3 and —OC(O)CF3; R2 is —OCH2C(O)NHNH—R5, wherein R5 is selected from the group consisting of (a) a phenyl group, optionally substituted with one or more of a halogen or a C1-C8 alkyl, which is optionally substituted with one or more of a first substitution group selected from the group consisting of a halogen, —OH, and —OR6, wherein R6 is C1-C8 alkyl, optionally substituted with one or more halogens; (b) a 2-, 3-, or 4-pyridyl, optionally substituted with one or more of a second substitution group selected from the group consisting of a halogen, —OH, and —OR6, where R6 is C1-C8 alkyl, optionally substituted with one or more halogens; (c) a heterocycle selected from the group consisting of imidazole, thiazole, benzimidizole, benzoxazole, benzthiazole, tetrazole, triazole, and aminothiazole; and (d) —C(O)R7, where R7 is selected from the group consisting of a C1-C20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, alkylaryl, and heterocycle, which is selected from the group consisting of pyridyl, imidazole, thiazole, benzimidizole, benzoxazole, benzthiazole, tetrazole, triazole, and aminothiazole; and R3 and R4 and independently selected from the group consisting of C1-C20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, and alkylaryl; with the proviso that when R1 is —H, —OCH3, or —OC(O)CF3 and R3 is —(CH2)7CH3, then R2 is not —OCH2C(O)NHNH—R5, where R5 is -p-C6H4Cl, —C(O)CH3, or ### Claim 47 (depends on 46) The method of claim 46, wherein the subject is a human. ### Claim 48 (depends on 47) The method of claim 47, wherein the compound is selected from the group consisting of: ### Claim 49 (depends on 46) The method of claim 46, wherein the subject is an animal. ### Claim 50 (depends on 49) The method of claim 49, wherein the compound is selected from the group consisting of: