Process for the preparation of quaternary N-alkyl morphinan...

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C546S045000, C546S046000

Reexamination Certificate

active

10530446

ABSTRACT:
A process for the preparation of a quaternary derivative of the morphinan alkaloid, the process comprising contacting a tertiary N-substituted morphinan alkaloid with an alkyl halide in an anhydrous solvent system, wherein the solvent system comprises an aprotic dipolar solvent with the aprotic dipolar solvent constituting at least 25 wt. % of the solvent system.

REFERENCES:
patent: 3101339 (1963-08-01), Zeile et al.
patent: 4141897 (1979-02-01), Olofson et al.
patent: 4176186 (1979-11-01), Goldberg et al.
patent: 4322426 (1982-03-01), Hermann et al.
patent: 4535157 (1985-08-01), Meltzer et al.
patent: 5240933 (1993-08-01), Merz et al.
patent: 5352680 (1994-10-01), Portoghese et al.
patent: 5574159 (1996-11-01), Chang et al.
patent: 5668285 (1997-09-01), Rice et al.
patent: 5869669 (1999-02-01), Huang et al.
patent: 5907069 (1999-05-01), Becnel et al.
patent: 5922876 (1999-07-01), Huang et al.
patent: 5948788 (1999-09-01), Huang et al.
patent: 5952495 (1999-09-01), Huang et al.
patent: 5981474 (1999-11-01), Manning et al.
patent: 6008354 (1999-12-01), Huang et al.
patent: 6008355 (1999-12-01), Huang et al.
patent: 6013796 (2000-01-01), Huang et al.
patent: 6365742 (2002-04-01), Mudryk et al.
patent: 2005/0182258 (2005-08-01), Schmidhammer et al.
patent: 124 001 (1985-07-01), None
patent: WO95/31463 (1995-11-01), None
patent: WO 2004/005294 (2004-01-01), None
Bognár, R., et al., “Selective Quaternization in the Morphine Series,”Tetrahedron Letters, 1964, pp. 2867-2871, No. 39.
International Search Report for PCT/US03/35463 dated Jul. 1, 2004, 3 pages.
Iorio, M.A., et al., “Diastereoisomeric Quaternary Morphinium Salts: Synthesis, Stereochemistry and Analgesic Properties,”European Journal of Medicinal Chemistry, 1984, pp. 11-16, vol. 19, No. 1.
Manoharan, T.S., et al., “Convenient Method for Replacement of Tertiary N-Methyl by Other Alkyl Groups: Application to Morphine Alkaloids,”Indian Journal of Chemistry, Jan. 1984, pp. 5-11, vol. 23B.
Musich et al., Reaction of O-methyl-N, N1-Diisopropylisourea with Amino Acids and Amines, Journal of Organic Chemistry (1977), 42(1), pp. 139-141.
Giger et al., Synthesis and Reactions of the diels-Alder Adduct of Thebaine with 4-phenyl-1,2,4-triazoline-3,5-dione, Tetrahedron (1973), 29(16), pp. 2387-2391.
Koczka et al., Selective Quaternization of Compounds with Morphine Skeleton, Acta. Chim. Acad. Sci. Hung. (1967), 51(4), pp. 393-402.
Seki, Isao, Studies on the Morphine Alkaloids and its Related Compounds. XIV. Preparation of 6-Amino-hydrophenanthrene Compounds from Hofmann Degradation Products of the Morphine Alkaloids, Chemical & Pharmaceutical Bulletin (1966), 14(5), pp. 453-461.
Fry et al., Mannich Derivatives of Analgesic Agents, Journal of Organic Chemistry (1959), 24, pp. 116-117.
Bentley et al., The Reduction of Thebaine and Dihydrothebaine by Sodium and Ammonia, Journal of the Chemical Society, Abstracts (1952), pp. 958-966.
Schultz et al., Thebaine Cyclopropanation, Russian Journal of Organic chemistry (Translation of Zhurnal Organicheskoi Khimii) (2003), 39(8), pp. 1083-1088.
Otto et al., Selection and Amplification of Hosts from Dynamic combinatorial Libraries of Macrocyclic Disulfides, Science (Washington, DC, United States) (2002), 297(5581), pp. 590-593 & Supporting Online Material.
Lopez et al., Photoxidation of Thebaine. A Route to 14-Hydroxymorphinones and Hydrodibenzofuran Analogs of Methadone, Tetrahedron Letters (1994), 35(31), pp. 5727-5730.
Manoharan et al., Stereoselectivity in Quaternization of Thebaine: 270 MHz PMR Spectroscopic Studies, Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal chemistry (1987), 26B(2), pp. 140-142.
Shults et al., Tranformations of Quaternary Tetrahydrothebaine Sulfones, Zh. Org. Khim. (1993), 29(6), pp. 1149-1162, (English pp. 953-963).
Funke et al., A1H and13C Nuclear Magnetic Resonance Study of Three Quaternary Salts of Naloxone and Oxymorphone, J. Chem. Soc. Perkin Trans. (1986) 2, pp. 735-738.
Lopez et al., The [4+2] Addition of Singlet Oxygen to Thebaine: New Access to Highly Functionalized Morphine Derivatives via Opioid Endoperoxides, J. Org. Chem. (2000), 65(15), pp. 4671-4678.

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Process for the preparation of quaternary N-alkyl morphinan... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for the preparation of quaternary N-alkyl morphinan..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the preparation of quaternary N-alkyl morphinan... will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-3902360

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.