Ring fused dihydropyrans, process for preparation and use...

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

Reexamination Certificate

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C514S455000, C514S456000, C514S459000, C514S460000, C549S361000, C549S364000, C549S386000, C549S387000, C549S398000, C549S399000

Reexamination Certificate

active

06399653

ABSTRACT:

The invention relates to compounds of the formula I
in which:
R
1
is
1. (C
1
-C
14
)-alkyl,
2. (C
2
-C
6
)-alkenyl,
3. (C
0
-C
6
)-alkyl-(C
3
-C
10
)-cycloalkyl-(C
0
-C
6
)-alkyl, where the alkyl moiety is optionally substituted by one or more OH groups,
4. (C
0
-C
6
)-alkyl-(C
6
-C
14
)-aryl,
5. (C
0
-C
6
)-alkyl-(C
3
-C
9
)-heteroaryl,
6. (C
2
-C
6
)-alkenyl-(C
6
-C
14
)-aryl,
7. (C
2
-C
6
)-alkenyl-(C
3
-C
9
)-heteroaryl,
8. (C
1
-C
6
)-alkanoyl,
9. a radical as defined under 4., 5., 6. or 7., where the (C
6
-C
14
)-aryl or (C
3
-C
9
)-heteroaryl moiety is substituted by 1, 2 or 3 identical or different radicals from the group consisting of (C
1
-C
10
)-alkyl, carboxyl, amino, nitro, (C
1
-C
4
)-alkylamino, hydroxyl, (C
1
-C
4
)-alkoxy, where one to all hydrogen atoms can be replaced by fluorine atoms, (C
6
-C
12
)-aryloxy, halogen, cyano, di-(C
1
-C
4
)-alkylamino, carbamoyl, sulfamoyl and (C
1
-C
4
)-alkoxycarbonyl, or two adjacent radicals on the (C
6
-C
12
)-aryl ring together are alkylenedioxy, preferably methylenedioxy;
R
2
is hydrogen, (C
1
-C
10
)-alkyl, (C
0
-C
6
)-alkyl-(C
6
-C
12
)-aryl or (C
0
-C
6
)-alkyl-(C
3
-C
9
)-heteroaryl, where the C
6
-C
12
-aryl or C
3
-C
9
-heteroaryl moiety is optionally substituted by 1, 2 or 3 identical or different radicals from the group consisting of carboxyl, amino, (C
1
-C
4
)-alkylamino, hydroxyl, (C
1
-C
4
)-alkoxy, halogen, cyano, di-(C
1
-C
4
)-alkylamino, carbamoyl, sulfamoyl and (C
1
-C
4
)-alkoxycarbonyl;
R
3
is —X—R
4
;
X is —O—, —NR
5
— or —S—;
R
4
is defined as R
1
;
 where R
4
together with R
2
can form a bridge member —CH
2
—CH
2
— or —CH
2
—CH
2
—CH
2
—;
R
5
is hydrogen or (C
1
-C
6
)-alkyl;
A is a fused cyclic ring system which
a) is substituted by one, two or three, preferably by one or two, oxo or hydroxyl functions, where one hydroxyl or oxo function is in the neighboring position to the dihydropyran ring, and
b) is mono, di- or polysubstituted, preferably mono- or disubstituted, by a (C
1
-C
10
)-alkyl radical or a carboxyl group, where at least one alkyl substituent carries a functional group, such as hydroxyl, carboxyl or amino;
and physiologically tolerable salts thereof.


REFERENCES:
patent: 3775435 (1973-11-01), Sellstedt et al.
patent: 5767116 (1998-06-01), Kerrigan et al.
Garrat, Vollhardt, Aromatizität, “7. Heterocyclische Systeme” pp. 131-153 (1973) Stuttgart.
Früchtel et al., “Organic Chemistry on Solid Supports”, Agnew. Chem. Int. Ed. Engl. 35:17-42 (1996).
L.F. Tietze, “Domino-Reactions: The Tandem-Knoevenagel-Hetero-Diels-Alder Reaction And Its Application In Natural Product Synthesis”, J. Heterocyclic Chem., 27(47):47-71 (1990).

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