Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
1999-11-16
2001-04-17
Kifle, Bruce (Department: 1611)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C548S537000
Reexamination Certificate
active
06218549
ABSTRACT:
BACKGROUND OF THE INVENTION
Throughout this application various patents and publications are referenced and citations are provided in parentheses. The disclosure of these patents and publications in their entireties are hereby incorporated by reference into this application in order to more fully describe the state of the art to which this invention pertains.
Many marine natural products contain the 2-aminoimidazole substructure. Certain members of this class of compounds appear to be biogenetically related, having diverged from a common, yet unidentified intermediate. Since the majority of these marine products have been isolated from depths ranging from 30 to 800 meters below sea level, metabolite availability has been a problem for chemical and biochemical investigations. Minute amounts contained in the marine source make it impractical to obtain suitable quantities of material necessary for further study. The present invention provides versatile and efficient methods of synthesizing these metabolites, and provides access to new compounds derived therefrom with anti-cancer, anti-hypertensive, anti-microbial and anti-viral properties. Certain new compounds are useful to treat central nervous system disorders such as shock, Parkinson's disease and ischemia.
SUMMARY OF THE INVENTION
The subject invention provides a bicyclic aminoimidazole compound having the structure
wherein n is an integer from 0 to about 5;
wherein R
1
is H; a C
1
to about C
10
alkyl group, which is a primary alkyl group, or a secondary branched alkyl group, or a tertiary branched alkyl group wherein the tertiary carbon of the tertiary branched alkyl group is separated from the ring structure of the bicyclic aminoimidazole compound by at least one carbon atom; a phenyl group; a thiophenyl group; a pyrrolyl group; a furanyl group; a benzyl group; or a pyridyl group;
which alkyl, phenyl, thiophenyl, pyrrolyl, furanyl, benzyl, or pyridyl groups are substituted or unsubstituted; and
wherein R
2
is H; a C
1
to about C
10
alkyl group, which is a straight chain alkyl group, or a branched alkyl group; or a phenyl group; which alkyl or phenyl groups are substituted or unsubstituted.
The subject invention provides a hydroxyalkyl aminoimidazole compound having the structure
wherein;
when R
3
is a substituted C
1
alkyl group; a C
2
to about C
10
alkyl group, which is a primary alkyl group, a secondary branched alkyl group, or a tertiary branched alkyl group wherein the tertiary carbon of the tertiary branched alkyl group is separated from the ring structure of the hydroxyalkyl aminoimidazole compound by at least one carbon atom, which alkyl groups are substituted or unsubstituted;
then R
4
is H; a C
1
to about C
10
straight chain alkyl group or branched alkyl group to which guanidine is attached wherein the guanidine is separated from the ring structure of the hydroxyalkyl aminoimidazole compound by at least one carbon atom; a C
1
to about C
10
straight chain alkyl group or branched alkyl group; a phenyl group; a thiophenyl group; a pyrrolyl group; a furanyl group; a benzyl group; or a pyridyl group; which alkyl to which guanidine is attached, alkyl, phenyl, thiophenyl, pyrrolyl, furanyl, benzyl, or pyridyl groups are substituted or unsubstituted; or;
when R
3
is H;
then R
4
is a C
1
to about C
10
straight chain alkyl group or branched alkyl group to which guanidine is attached wherein the guanidine is separated from the ring structure of the hydroxyalkyl aminoimidazole compound by at least one carbon atom; a C
1
to about C
10
straight chain alkyl group or branched alkyl group; a phenyl group; a thiophenyl group; a pyrrolyl group; a furanyl group; a benzyl group; or a pyridyl group; which alkyl to which guanidine is attached, alkyl, phenyl, thiophenyl, pyrrolyl, furanyl, benzyl, or pyridyl groups are substituted or unsubstituted.
The subject invention provides a bicyclic pyrrole compound having the structure
wherein n is an integer from 1 to about 6;
wherein R
5
and R
6
are the same or different, and are H; a C
1
to about C
10
straight chain alkyl group or branched alkyl group, which alkyl groups are substituted or unsubstituted; or halogen.
The subject invention provides a hymenin compound having the structure
wherein R
5
and R
6
are the same or different, and are H; a C
1
to about C
10
straight chain alkyl group or branched alkyl group, which alkyl group is substituted or unsubstituted; or F, Cl, or I.
The subject invention provides an aldehyde aminoimidazole compound having the structure
wherein R
5
and R
6
are the same or different, and are H; a C
1
to about C
10
straight chain alkyl group or branched alkyl group, which alkyl group is substituted or unsubstituted; or halogen.
The subject invention provides a ketal aminoimidazole compound having the structure
wherein R
5
and R
6
are the same or different, and are H; a C
1
to about C
10
straight chain alkyl group or branched alkyl group, which alkyl group is substituted or unsubstituted; or halogen.
The subject invention provides a tricyclic compound having the structure
The subject invention provides a tetrahydropurine compound having the structure
wherein R
7
is a C
1
to about C
10
alkyl group, which is a primary alkyl group, a secondary branched alkyl group, or a tertiary branched alkyl group wherein the tertiary carbon of the tertiary branched alkyl group is separated from the ring structure of the tetrahydropurine compound by at least one carbon atom, which alkyl groups are substituted or unsubstituted.
REFERENCES:
patent: 3746705 (1973-07-01), Cavalleri et al.
patent: 4812462 (1989-03-01), Blankley et al.
patent: 5091390 (1992-02-01), Ardecky et al.
patent: 5621099 (1997-04-01), Annovra et al.
patent: 2016437 (1990-11-01), None
patent: WO8707274 (1987-12-01), None
Abstract. Xu et al. (Tetrahedron Lett. (1994), 35(3), 351-4.*
Braun, M., et al., Journal of the American Chemical Society (1978), “Synthesis of Parazoanthoxanthins and Pseudozoanthoxanthins,” vol. 100, pp. 4208-4213; U.S.A.
Braun, M., et al., Journal of the American Chemical Society (1976), “Synthesis of Zoanthoxanthins,” vol. 32, pp. 3049-3050; U.S.A.
Colson, Genevieve et al., “Mode of Action of the Antitumor Compound Girodazole”, Chemical Abstracts 117: 82994y, (1992).
Commercon, A., et al., Tetrahedron Letters (1991), “A Diastereoselective Synthesis of Girolline,” vol. 32, pp. 1419-1422; U.K.
Dalkafouki, A., et al., Tetrahedron Letters (1991), “Sysnthesis of 2-Dimethylaminoimidazole Derivatives: A New Access to Indolyl-imidazole Alkaloids of Marine Origina,” vol. 32 pp., 5325-5328; U.K.
Fernandez-Bolanos, J., et al., “Synthesis of 1-Alkyl (or H) -4-(D-lyxo-tetritol-l-yl) -4-imidazolin-2-ylideneammonium Picrates and Chlorides” Chemical Abstracts 116: 255934p, (1992).
Grimmett, M.R., “imidazoles and their Benzo Derivatives: (ii) Reactivity,” in Comprehensive Heterocyclic Chemistry: The Structure, Reactions, Synthesis and Uses Heterocyclic Compounds, Potts, K.T., et.; Pergamon Press, New York (1984), vol. 5, pp. 404-405; U.S.A.
Kobayaski, J., et al., “&agr;-Adrenoceptor blocking action of hymenin, a novel marine alkaloid ”, Chemical Abstracts, 108(15): 124371q (1988).
Kobayaski, J., et al., “&agr;-Adrenoceptor blocking action of hymenin, a novel marine alkaloid”, Experientia 44(1), pp. 86-87 (1988).
Lancini, G., et al., United Kingdon patent 1,132,013, “Imidazole Derivatives,” published Oct. 30, 1968.
Lancini, G., et al., Journal of Heterocyclic Chemistry (1966), “A New Synthesis of Alkyl and Aryl 2-Amino-imidazoles,” vol. 3, pp. 152-154; U.S.A.
Ruccia, M., et al, Tetrahedron (1974), “Mononuclear Heterocyclic Rearrangements-VI: Conversion of 1,2,4-Oxadiazoles into Imidazoles,” vol. 30, pp. 3859-3864; U.K.
Walker, R., et al, Journal of the American Chemical Society (1981), “Sceptrin, an Antimicrobia Agent from the sponge Agelas Sceptrum,” vol. 103, pp. 6772-6773; U.S.A.
Xu, Y., et al., “Reactions 2-Aminoimidazoles with Aldehydes. Hydroxyalkylation and Cycloaddition”, Tetrahedron Letters (1993), 34(44):6981-6984.
Zurita, M., et al., Tetrahedron Let
Horne David A.
Yakushijin Kenichi
Cooper & Dunham LLP
Kifle Bruce
The Trustees of Columbia University in the City of New York
White John P.
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