Method of preparing 4-amino-1 H -imidazo (4,5- c )...

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

C514S292000

Reexamination Certificate

active

08080662

ABSTRACT:
The present invention provides a method of preparing a 4-(arylmethyl)amino-1H-imidazo(4,5-c)quinoline of formula (4) by reacting an arylmethylamine of formula (3) with a 4-chloro-1H-imidazo(4,5-c)quinoline of formula (2). The present invention further provides a method of preparing an acid addition salt of formula (5) comprising the step of hydrolyzing a 4-(arylmethyl)amino-1H-imidazo(4,5-c)quinoline of formula (4) with a strong acid, HX. The present invention further provides a method of preparing a 4-amino-1H-imidazo(4,5-c)quinoline of formula (1) comprising the step of treating an acid addition salt of formula (5) with a base.

REFERENCES:
patent: 4689338 (1987-08-01), Gerster
patent: 4698348 (1987-10-01), Gerster
patent: 4929624 (1990-05-01), Gerster et al.
patent: 5037986 (1991-08-01), Gerster
patent: 5175296 (1992-12-01), Gerster
patent: 5346905 (1994-09-01), Gerster
patent: 5352784 (1994-10-01), Nikolaides et al.
patent: 5367076 (1994-11-01), Gerster
patent: 5389640 (1995-02-01), Gerster et al.
patent: 5395937 (1995-03-01), Nikolaides et al.
patent: 5494916 (1996-02-01), Lindstrom et al.
patent: 5578727 (1996-11-01), Andre et al.
patent: 5741908 (1998-04-01), Gerster et al.
patent: 6069149 (2000-05-01), Nanba et al.
patent: 6194425 (2001-02-01), Gerster et al.
patent: 6255502 (2001-07-01), Penkler et al.
patent: 6376669 (2002-04-01), Rice et al.
patent: 6583317 (2003-06-01), Moens
patent: 6608201 (2003-08-01), Gerster et al.
patent: 6624305 (2003-09-01), Gerster et al.
patent: 2004/0138459 (2004-07-01), Merli et al.
patent: 145340 (1985-06-01), None
patent: 310950 (1989-04-01), None
patent: WO-98/30562 (1998-07-01), None
patent: WO-9929693 (1999-06-01), None
patent: WO-2004009593 (2004-01-01), None
“Amine,” Wikipedia, <http://en.wikipedia.org/w/index.php?title=Amine&printable=yes>, accessed Feb. 1, 2008 (8 pages).
“Hydrolysis,” Wikipedia, http://en.wikipedia.org/w/index.php?title=Hydrolysis&printable=yes, accessed Dec. 15, 2008 (5 pages).
Aggarwal et al., “Highly diastereoselective nitrone cycloaddition onto a chiral ketene equivalent: Asymmetric synthesis of cispentacin,” Org. Lett., 2002, 4, 1227-1229.
B.L. Hutchings et al., “A Chemical Method for the Determination of Pteroylglutamic Acid and Related Compounds,” J. Biological Chem., v. 168 (1947) pp. 705-710.
G.V. Smith & F. Notheisz, “Heterogeneous Catalysis in Organic Chemistry,” Academic Press (1999) pp. 119, 160-180, 202-218.
H.T. Clarke et al., “The Action of Formaldehyde on Amines and Amino Acids,” J. Am. Chem. Soc., v. 55 (Nov. 1933) pp. 4571-4587.
International Search Report (Apr. 28, 2005) for PCT/US2004/032243.
International Preliminary Report on Patentability (Apr. 3, 2006) and Written Opinion (Apr. 28, 2005) for PCT/US2004/032243.
M.G. Loudon, “Organic Chemistry,” Addison-Wesley (1984) p. 1059.
R.T. Morrison & R.N. Boyd, “Organic Chemistry,” 3rd ed., Allyn and Bacon (1976) pp. 680-684.
S.L. Seager & M.R. Slabaugh, “Chemistry for Today: General, Organic, and Biochemistry,” Brooks/Cole (2000) pp. 285-286.
Shen et al., “Study on the synthesis of imiquimod,” Chem. Res. & Appln., 2001, 13, 249-252 (original Chinese and certified English translation).
Tam, James et al, “Mechanisms for the Removal of Benzyl Proecting Group in Synthetic Peptides by Trifluoromethanexulfonic Acid-Trifluoroacetic Acid-Dimethyl Sulfide”, Journal of the American Chemical Society. vol. 108, No. 17, pp. 5242-5251, 1986.
V.I. Maksimov & N. D. Zelinskii, “Fragmentation of activated n,n-dibenzyl-3-phenylalanine derivatives,” Russian Chem. Bulletin, v. 11, n. 1 (Jan. 1962) pp. 99-105 (English-language summary, http://www.springerlink.com/content/m54528x4607154x1/, accessed Nov. 29, 2006 (3 pages)).
Wikepedia definition of hydrogenolysis 2008.
Weast et al., eds., “CRC Handbook of Chemistry and Physics, 69th Edition,” CRC Press, Inc., Boca Raton, FL, pp. D-161 to D-163, 1988-1989.

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

Method of preparing 4-amino-1 H -imidazo (4,5- c )... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Method of preparing 4-amino-1 H -imidazo (4,5- c )..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method of preparing 4-amino-1 H -imidazo (4,5- c )... will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-4316271

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