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Volumn 16, Issue 24, 2008, Pages 10295-10300

Polyethylene glycol-based homologated ligands for nicotinic acetylcholine receptors

Author keywords

A 84543; ADMP; DMPP; Pyridyl ethers; SAR

Indexed keywords

A 84543; CHOLINE DERIVATIVE; MACROGOL DERIVATIVE; NICOTINIC RECEPTOR; PIPERAZINE DERIVATIVE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 56349165633     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.10.045     Document Type: Article
Times cited : (13)

References (50)
  • 1
    • 56349096099 scopus 로고    scopus 로고
    • Nicotinic see: Brown, J. H.; Taylor, P. In Goodman and Gilman's Pharmacological Basis of Therapeutics, 10th ed.; Hardman, J. G.; Limbird, L. E., Eds., New York: McGraw-Hill, Chapter 9, pp. 193-213.
    • Nicotinic see: Brown, J. H.; Taylor, P. In Goodman and Gilman's Pharmacological Basis of Therapeutics, 10th ed.; Hardman, J. G.; Limbird, L. E., Eds., New York: McGraw-Hill, Chapter 9, pp. 193-213.
  • 2
    • 56349103815 scopus 로고    scopus 로고
    • Muscarinic, see: Brown, J. H.; Taylor, P. In Goodman and Gilman's Pharmacological Basis of Therapeutics, 10th ed.; Hardman, J. G.; Limbird, L. E., Eds., New York: McGraw-Hill, Chapter, Chapter 7 pp. 154-173.
    • Muscarinic, see: Brown, J. H.; Taylor, P. In Goodman and Gilman's Pharmacological Basis of Therapeutics, 10th ed.; Hardman, J. G.; Limbird, L. E., Eds., New York: McGraw-Hill, Chapter, Chapter 7 pp. 154-173.
  • 11
    • 56349117776 scopus 로고    scopus 로고
    • Lin, N. H.; He, Y.; Holladay, M. W.; Ryther, K.; Li, Y. 3-Pyridyloxymethyl Heterocyclic Ether Compounds Useful in Controlling Chemical Synaptic Transmission. Patent US 5,629,325, 1997.
    • Lin, N. H.; He, Y.; Holladay, M. W.; Ryther, K.; Li, Y. 3-Pyridyloxymethyl Heterocyclic Ether Compounds Useful in Controlling Chemical Synaptic Transmission. Patent US 5,629,325, 1997.
  • 20
    • 56349109231 scopus 로고    scopus 로고
    • Bentley, M.D.; Bossard, M.J.; Burton, K.W.; Viegas, Tacey X. Poly(ethylene) Glycol Conjugates of Biopharmaceuticals, In Drug Delivery in Modern Biopharmaceuticals. Berlin: Wiley-VCH, 2005; Vol. 4, pp. 1193-1418.
    • Bentley, M.D.; Bossard, M.J.; Burton, K.W.; Viegas, Tacey X. Poly(ethylene) Glycol Conjugates of Biopharmaceuticals, In Drug Delivery in Modern Biopharmaceuticals. Berlin: Wiley-VCH, 2005; Vol. 4, pp. 1193-1418.
  • 27
    • 56349148055 scopus 로고    scopus 로고
    • note
    • For consistency the letter system for each series is such that a-g represent 0-6 ethylene oxide units. Thus, compound 4a is simply methanol and mesylate 5a does not appear.
  • 33
    • 56349112101 scopus 로고    scopus 로고
    • Matter, M.; Rossi, A.; von Sprecher, H. Polyglycol Ether Acid Anilides. US Patent 2,769,838, 1956.
    • Matter, M.; Rossi, A.; von Sprecher, H. Polyglycol Ether Acid Anilides. US Patent 2,769,838, 1956.
  • 34
    • 56349160337 scopus 로고    scopus 로고
    • Belaby, R.; Hazard, R.; Cheymol, J.; Chabrier, P.; Najer, H. "Diuréthans et Leur Préparation" Fr. 1,173,901, 1959, Chem. Abstr. 1962, 56, 1354f.
    • Belaby, R.; Hazard, R.; Cheymol, J.; Chabrier, P.; Najer, H. "Diuréthans et Leur Préparation" Fr. 1,173,901, 1959, Chem. Abstr. 1962, 56, 1354f.
  • 37
    • 56349156763 scopus 로고    scopus 로고
    • note
    • This is a fairly standard method for quaternization of amines and worked well for the preparation of ADMP, AaCh and lower mPEG oligomers (n = 0-2), affording crystalline compounds. However, crystallization of the higher oligomers proved more difficult and in many cases, we were unable to obtain precipitates from acetone or acetonitrile and addition of ether or hydrocarbon solvents produced only oils. While we do not have an explanation for this, the compounds gave satisfactory HRMS and NMR data (see Section 4).
  • 41
    • 56349140827 scopus 로고    scopus 로고
    • note
    • An excess of the alkyne is required as the alkynylpyridine product is virtually inseparable from the starting bromopyridine and thus the reaction must be forced to completion.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.