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- Nachgewiesen in: USPTO Patent Grants
- Sprachen: English
- Patent Number: 9,175,001
- Publication Date: November 03, 2015
- Appl. No: 14/349230
- Application Filed: October 02, 2012
- Assignees: TRUSTEES OF BOSTON UNIVERSITY (Boston, MA, US)
- Claim: 1. A compound of structural formula XIV, XV or XVI; [chemical expression included] or a pharmaceutically acceptable salt thereof wherein, each X is independently O or S; R 1 is hydrogen or an alkyl, alkenyl, alkynyl, aryl, heteroaryl or arylalkyl group; R 2 is hydrogen or a hydroxyl, alkoxy, phenoxy, alkyl, alkenyl, alkynyl, aryl, heteroaryl or arylalkyl group; each R 3 and each R 6 is: (i) independently hydrogen, fluorine, chlorine, bromine, iodine or a hydroxyl, alkoxy, phenoxy, alkyl, alkenyl, alkynyl, aryl, heteroaryl or arylalkyl group; or (ii) the two R 6 moieties and/or the two R 3 moieties taken together with an alkylene, alkenylene or alkynylene group form a substituted or unsubstituted C3 to C6 ring; and R 4 , R 5 , R 7 , R 8 , R 9 , R 10 R 11 and R 12 are each independently hydrogen, fluorine, chlorine, bromine, iodine or a hydroxyl, alkoxy, phenoxy, alkyl, alkenyl, alkynyl, aryl, heteroaryl or arylalkyl group.
- Claim: 2. The compound of claim 1 , wherein for structural formulas XIV, XV or XVI: each X is O or S; R 1 is hydrogen or a methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, substituted or unsubstituted phenyl or substituted or unsubstituted benzyl group; R 2 is hydrogen or a hydroxyl, methoxy, ethoxy, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, phenyl or benzyl group; each R 3 and each R 6 is independently hydrogen, fluorine, chlorine, bromine, iodine or a hydroxyl, methoxy, ethoxy, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, phenyl or benzyl group; and R 4 , R 5 , R 7 , R 8 , R 9 , R 10 R 11 and R 12 are each independently hydrogen, fluorine, chlorine, bromine, iodine or a hydroxyl, methoxy, ethoxy, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, phenyl or benzyl group.
- Claim: 3. The compound of claim 2 , wherein the compound of structural formula XIV, XV or XVI is a compound having the structural formula IV, V or VI; [chemical expression included] or a pharmaceutically acceptable salt thereof.
- Claim: 4. A composition comprising a compound of formula XIV, XV or XVI; [chemical expression included] or a pharmaceutically acceptable salt thereof wherein, each X is independently O or S; R 1 is hydrogen or an alkyl, alkenyl, alkynyl, aryl, heteroaryl or arylalkyl group; R 2 is hydrogen or a hydroxyl, alkoxy, phenoxy, alkyl, alkenyl, alkynyl, aryl, heteroaryl or arylalkyl group; each R 3 and each R 6 is: (i) independently hydrogen, fluorine, chlorine, bromine, iodine or a hydroxyl, alkoxy, phenoxy, alkyl, alkenyl, alkynyl, aryl, heteroaryl or arylalkyl group; or (ii) the two R 6 moieties and/or the two R 3 moieties taken together with an alkylene, alkenylene or alkynylene group form a substituted or unsubstituted C3 to C6 ring; and R 4 , R 5 , R 7 , R 8 , R 9 , R 10 R 11 and R 12 are each independently hydrogen, fluorine, chlorine, bromine, iodine or a hydroxyl, alkoxy, phenoxy, alkyl, alkenyl, alkynyl, aryl, heteroaryl or arylalkyl group.
- Claim: 5. The composition of claim 4 , wherein for the compound of formula XIV, XV or XVI: each X is O or S; R 1 is hydrogen or a methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, substituted or unsubstituted phenyl or substituted or unsubstituted benzyl group; R 2 is hydrogen or a hydroxyl, methoxy, ethoxy, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, phenyl or benzyl group; each R 3 and each R 6 is independently hydrogen, fluorine, chlorine, bromine, iodine or a hydroxyl, methoxy, ethoxy, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, phenyl or benzyl group; and R 4 , R 5 , R 7 , R 8 , R 9 , R 10 R 11 and R 12 are each independently hydrogen, fluorine, chlorine, bromine, iodine or a hydroxyl, methoxy, ethoxy, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, phenyl or benzyl group.
- Claim: 6. The composition of claim 5 , wherein the compound of structural formula XIV, XV or XVI is a compound having the structural formula IV, V or VI: [chemical expression included] or a pharmaceutically acceptable salt thereof.
- Claim: 7. The composition of claim 4 , wherein said composition further comprises a pharmaceutically acceptable carrier.
- Claim: 8. A method comprising administering to a subject, to inhibit or treat LSF in said subject, an effective amount of a compound of structural formula XIV, XV or XVI; [chemical expression included] or a pharmaceutically acceptable salt thereof, wherein, each X is independently O or S; R 1 is hydrogen or an alkyl, alkenyl, alkynyl, aryl, heteroaryl or arylalkyl group; R 2 is hydrogen or a hydroxyl, alkoxy, phenoxy, alkyl, alkenyl, alkynyl, aryl, heteroaryl or arylalkyl group; each R 3 and each R 6 is: (i) independently hydrogen, fluorine, chlorine, bromine, iodine or a hydroxyl, alkoxy, phenoxy, alkyl, alkenyl, alkynyl, aryl, heteroaryl or arylalkyl group; or (ii) the two R 6 moieties and/or the two R 3 moieties taken together with an alkylene, alkenylene or alkynylene group form a substituted or unsubstituted C3 to C6 ring; and R 4 , R 5 , R 7 , R 8 , R 9 , R 10 R 11 and R 12 are each independently hydrogen, fluorine, chlorine, bromine, iodine or a hydroxyl, alkoxy, phenoxy, alkyl, alkenyl, alkynyl, aryl, heteroaryl or arylalkyl group.
- Claim: 9. A method of determining the expression or activity of LSF comprising: a) contacting a cancerous cell or cancerous tissue with a compound of claim 1 ; and b) monitoring, directly or indirectly, the expression or activity of LSF associated with said cancerous cell or cancerous tissue.
- Claim: 10. A method of determining the expression or activity of LSF comprising: a) contacting a cancerous cell or cancerous tissue with a composition of claim 4 ; and b) monitoring, directly or indirectly, the expression or activity of LSF associated with said cancerous cell or cancerous tissue.
- Patent References Cited: 5968952 October 1999 Venet et al. ; 2012050985 April 2012 ; WO2012050985 April 2012 ; 2012027392 May 2012
- Other References: CAPLUS 2008:1549605. cited by examiner ; CAPLUS 2008 1549605. cited by examiner ; Li-Ping Guan et al: “Synthesis and Anticonvulsant Activity of 5-Phenyl-[1,2,4]-triazolo[4,3- a ]quinolines”, Archiv Der Pharmazie, 341(12):774-779 (Dec. 1, 2008). cited by applicant ; Pragya Singh et al: “Design and Synthesis of C-Ring Lactone- and Lactam-Based Podophyllotoxin Analogues as Anticancer Agents”, Chemical & Pharmaceutical Bulletin, 58(2):242-246 (Feb. 1, 2010). cited by applicant ; Yu-Hsun Chang et al: “Design and Synthesis of 2-(3-Benzo[ b ]thienyl)-6,7-methylenedioxyquinolin-4-one Analogues as Potent Antitumor Agents that Inhibit Tubulin Assembly”, Journal of Medicinal Chemistry, 52 (15):4883-4891 (Aug. 13, 2009). cited by applicant
- Primary Examiner: Reese, Heidi
- Attorney, Agent or Firm: Nixon Peabody LLP
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