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Indole alkaloid derivatives having opioid receptor agonistic effect, and therapeutic compositions and methods relating to same

Foreign code F130007259
File No. P07-074US-D1
Posted date Apr 3, 2013
Country United States of America
Application number 201213549564
Gazette No. 20120276195
Gazette No. 8648090
Date of filing Jul 16, 2012
Gazette Date Nov 1, 2012
Gazette Date Feb 11, 2014
Priority data
  • 2007US-60986370 (Nov 8, 2007) US
  • 2008US-12266579 (Nov 7, 2008) US
Title Indole alkaloid derivatives having opioid receptor agonistic effect, and therapeutic compositions and methods relating to same
Abstract (US8648090)
Indole alkaloid derivatives having an opioid receptor agonistic effect, their synthesis, and therapeutic compositions containing these derivatives, and methods of treating conditions with these compounds and therapeutic compositions, are provided.
Scope of claims [claim1]
1. A compound having the formula:

wherein R1 is a halogen atom, hydrogen atom, or a nitro group or alkoxy group and R2 is a hydrogen atom or halogen atom or nitro group.
[claim2]
2. A compound having the formula:

wherein R1.dbd.F, R2.dbd.H; R1.dbd.Cl, R2.dbd.H; R1.dbd.H, R2.dbd.Cl; R1.dbd.Br, R2.dbd.H; R1.dbd.H, R2.dbd.Br; R1.dbd.NO2, R2.dbd.H; R1.dbd.H, R2.dbd.NO2; or R1.dbd.OMe, R2.dbd.H.
[claim3]
3. A pharmaceutical composition comprising a therapeutic amount of a compound of claim 1 or a pharmaceutically acceptable salt thereof.
[claim4]
4. The pharmaceutical composition of claim 3 in a pharmaceutically deliverable form selected from the group consisting of solutions, suspensions, emulsions, tablets, pills, pellets, granules, lozenges, capsules, capsules containing liquids, powders, sustained-release formulations, syrups, elixirs, creams, gels, suppositories, emulsions, aerosols, and sprays.
[claim5]
5. A pharmaceutical composition containing 0.1% to 100% of said compound of claim 1 or a pharmaceutically acceptable salt thereof.
[claim6]
6. A method for eliciting a therapeutic effect in a patient in need thereof, comprising the step of administering to said patient an effective dose of the 2,3-ethylene glycol bridged indoline adduct compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein said therapeutic effect is an analgesic effect.
[claim7]
7. The method of claim 6 wherein said step of administering is performed by a delivery route selected from the group consisting of oral, transdermal, inhalation, injection, infusion, and suppository.
[claim8]
8. The method of claim 6 wherein said patient is an animal.
[claim9]
9. The method of claim 6 wherein said patient is a mammal.
[claim10]
10. The method of claim 6 wherein said patient is a human.
[claim11]
11. The method of claim 6 wherein patient is a human and the therapeutic effect is pain treatment, where an effective total daily dosage of said compound ranges from about 0.1 mg to about 1,000 mg active compound/kg body weight of said patient.
[claim12]
12. A method for making the 2,3-ethylene glycol bridged indoline adduct compound of claim 1, comprising the steps of: reacting a Corynanthe-type indole alkaloid with hypervalent iodine in the presence of ethylene glycol effective to provide a 2,3-ethylene glycol bridged indoline adduct, effective to mask a 2,3-n bond of an indole nucleus of said adduct.
[claim13]
13. The method of claim 12 further comprising introducing a halogen atom at a C10 position of the adduct via electrophilic aromatic substitution, providing a C10-halogenated adduct derivative.
  • Inventor, and Inventor/Applicant
  • TAKAYAMA HIROMITSU
  • KITAJIMA MARIKO
  • MATSUMOTO KENJIRO
  • HORIE SYUNJI
  • CHIBA UNIVERSITY
  • JOSAI UNIVERSITY
IPC(International Patent Classification)
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