Carboxamide-substituted phenylurea derivatives, process for...

Details Carboxamide-substituted phenylurea derivatives, process for... Carboxamide-substituted phenylurea derivatives, process for...

2002-05-24

2004-11-02

Desai, Rita (Department: 1625)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Nitrogen containing other than solely as a nitrogen in an...

C514S596000, C514S597000, C564S044000, C564S047000

Reexamination Certificate

active

06812250

ABSTRACT:

This application claims the benefit of foreign priority under 35 U.S.C. §119 of German patent application no. 10125567.5, filed on May 25, 2001 and German patent application no10207369.4, filed on Jan. 21, 2002 the contents of both of which are incorporated by reference herein.
The invention relates to carboxamide-substituted phenylurea derivatives and their physiologically tolerated salts and physiologically functional derivatives.
Acylphenylurea derivatives of similar structure have already been described in the prior art as insecticides (EP 0 136 745, EP 0 167 197, DE 29 26 480, J. Agric. Food Chem. 1999, 47, 3116-3424).
In one embodiment, the invention is based on the object of providing compounds which display a blood glucose-lowering effect which can be utilized in therapy.
The invention therefore, for example, relates to compounds of the formula I,
in which
A is phenyl or naphthyl, where the phenyl or naphthyl is unsubstituted or substituted 1, 2, or 3 times wherein each substituent is independently chosen from F, Cl, Br, OH, CF
3
, NO
2
, CN, OCF
3
, O—(C
1
-C
6
)-alkyl, O—(C
2
-C
6
)-alkenyl, O—(C
2
-C
6
)-alkynyl, S—(C
1
-C
6
)-alkyl, S—(C
2
-C
6
)-alkenyl, S—(C
2
-C
6
)-alkynyl, SO—(C
1
-C
6
)-alkyl, SO
2
—(C
1
-C
6
)-alkyl, SO
2
—NH
2
, (C
1
-C
6
)-alkyl, (C
2
-C
6
)-alkenyl, (C
2
-C
6
)-alkynyl, (C
3
-C
7
)-cycloalkyl, (C
3
-C
7
)-cycloalkyl-(C
1
-C
4
)-alkylene, (C
0
-C
6
)-alkylene-COOH, (C
0
-C
6
)-alkylene-COO—(C
1
-C
7
)-alkyl, (C
0
-C
6
)-alkylene-COO—(C
2
-C
7
)-alkenyl, CONH
2
, CONH—(C
1
-C
6
)-alkyl, CON—[(C
1
-C
6
)-alkyl]
2
, CONH—(C
3
-C
6
)-cycloalkyl, (C
0
-C
6
)-alkylene-NH
2
, (C
0
-C
6
)-alkylene-NH—(C
2
-C
6
)-alkyl, (C
0
-C
6
)-alkylene-N—[(C
1
-C
6
)-alkyl]
2
, NH—CO—(C
1
-C
6
)-alkyl, NH—CO-phenyl, and NH—SO
2
-phenyl, wherein the phenyl of NH—CO-phenyl and NH—SO
2
-phenyl is unsubstituted or substituted 1 or 2 times wherein each substituent is independently chosen from F, Cl, CN, OH, (C
1
-C
6
)-alkyl, O—(C
1
-C
6
)-alkyl, CF
3
, OCF
3
, COOH, COO—(C
1
-C
6
)-alkyl and CONH
2
;
R1, R2 are, independently of one another, H, (C
1
-C
6
)-alkyl, O—(C
1
-C
6
)-alkyl, CO—(C
1
-C
6
)-alkyl, or COO—(C
1
-C
6
)-alkyl;
R3, R4, R5, R6 are, independently of one another, H, F, Cl, Br, OH, CF
3
, NO
2
, CN, OCF
3
, O—(C
1
-C
6
)-alkyl, O—(C
2
-C
6
)-alkenyl, O—(C
2
-C
6
)-alkynyl, S—(C
1
-C
6
)-alkyl, S—(C
2
-C
6
)-alkenyl, S—(C
2
-C
6
)-alkynyl, SO—(C
1
-C
6
)-alkyl, SO
2
—(C
1
-C
6
)-alkyl, SO
2
—NH
2
, (C
1
-C
6
)-alkyl, (C
2
-C
6
)-alkenyl, (C
2
-C
6
)-alkynyl, (C
3
-C
7
)-cycloalkyl, (C
3
-C
7
)-cycloalkyl-(C
1
-C
4
)-alkylene, COOH, COO—(C
1
-C
6
)-alkyl, CO—NH
2
, CO—NH—(C
1
-C
6
)-alkyl, CO—N—[(C
1
-C
6
)-alkyl]
2
, CO—NH—(C
3
-C
7
)-cycloalkyl, NH
2
, NH—(C
1
-C
6
)-alkyl, N—[(C
1
-C
6
)-alkyl]
2
, NH—CO—(C
1
-C
6
)-alkyl, NH—CO-phenyl, or NH—SO
2
-phenyl, wherein the phenyl of NH—CO-phenyl and NH—SO
2
-phenyl is unsubstituted or substituted 1 or 2 times wherein each substituent is independently chosen from F, Cl, CN, OH, (C1-C6)-alkyl, O—(C1-C
6
)-alkyl, CF
3
, OCF
3
, COOH, COO—(C
1
-C
6
)-alkyl and CO—NH
2
;
R7 is H, (C
1
-C
6
)-alkyl, or CO(C
1
-C
6
)-alkyl;
R8 is H, (C
1
-C
10
)-alkyl, where the alkyl is unsubstituted or substituted 1, 2, or 3 times wherein each substituent is independently chosen from OH, CF
3
, CN, COOH, COO—(C
1
-C
6
)-alkyl, CO—NH
2
, NH
2
, NH—(C
1
-C
6
)-alkyl, N—[(C
1
-C
6
)-alkyl]
2
, NCO—(C
1
-C
6
)-alkyl, NCOO—(C
1
-C
6
)-alkyl, NCOO—(C
1
-C
6
)-alkenyl, NCOO—(C
1
-C
6
)-alkynyl and NCOO—(C
1
-C
4
)-alkylene-(C
6
-C
10
)-aryl; or
(CH
2
)
m
-aryl, where m ranges from 0-6, and aryl is phenyl, O-phenyl, CO-phenyl, benzo[1,3]dioxolyl, heterocycloalkyl, pyridyl, indolyl, piperidinyl, tetrahydronaphthyl, naphthyl, 2,3-dihydro-benzo[1,4]dioxinyl, benzo[1,2,5]thiadiazolyl, pyrrolidinyl, or morpholinyl, where the aryl is unsubstituted or substituted by at least one R9;
R9 is F, Cl, Br; OH, NO
2
, CF
3
, OCF
3
, (C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl-OH, O—(C
1
-C
6
)-alkyl, S—(C
1
-C
6
)-alkyl, (C
1
-C
4
)-alkylphenyl, COOH, or COO—(C
1
-C
6
)-alkyl;
and their physiologically tolerable salts.
In one embodiment, the compounds of the formula I are those in which
A is phenyl, where the phenyl is unsubstituted or substituted 1, 2, or 3 times wherein each substituent is independently chosen from F, Cl, and Br;
R1, R2 are H;
R3, R4, R5, R6 are, independently of one another, H, F, Cl, Br, NO
2
, O—(C
1
-C
6
)-alkyl, or (C
1
-C
6
)-alkyl;
R7 is H, or CH
3
;
R8 is H, (C
1
-C
10
)-alkyl, where the alkyl is unsubstituted or substituted 1, 2, or 3 times wherein each substituent is independently chosen from OH, CF
3
, CN, COOH, COO—(C
1
-C
6
)-alkyl, CO—NH
2
, NH
2
, NH—(C
1
-C
6
)-alkyl, N—[(C
1
-C
6
)-alkyl]
2
, NCO—(C
1
-C
6
)-alkyl, NCOO—(C
1
-C
6
)-alkyl, NCOO—(C
1
-C
6
)-alkenyl, NCOO—(C
1
-C
6
)-alkynyl or NCOO—(C
1
-C
4
)-alkylene-(C
6
-C
10
)-aryl; or
(CH2)m-aryl, where m ranges from 0-6, and aryl is phenyl, O-phenyl, CO-phenyl, benzo[1,3]dioxolyl, heterocycloalkyl, pyridyl, indolyl, piperidinyl, tetrahydronaphthyl, naphthyl, 2,3-dihydro-benzo[1,4]dioxinyl, benzo[1,2,5]thiadiazolyl, pyrrolidinyl, morpholinyl, where the aryl is unsubstituted or substituted by at least one R9;
R9 is F, Cl, Br; OH, NO
2
, CF
3
, OCF
3
, (C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl-OH, O—(C
1
-C
6
)-alkyl, S—(C
1
-C
6
)-alkyl, (C
1
-C
4
)-alkylphenyl, COOH, or COO—(C
1
-C
6
)-alkyl;
and their physiologically tolerable salts.
In another embodiment, the compounds of the formula I are those in which
A is phenyl, where the phenyl is unsubstituted or substituted 1, 2, or 3 times wherein each substituent is independently chosen from F, Cl, and Br;
R1, R2 are H;
R3, R4, R5, R6 are, independently of one another, H, F, Cl, Br, NO
2
, O—(C
1
-C
6
)-alkyl, or (C
1
-C
6
)-alkyl;
R7 is H, or CH
3
;
R8 is (C
1
-C
10
)-alkyl, where the alkyl is unsubstituted or substituted 1, 2, or 3 times wherein each substituent is independently chosen from OH, CF
3
, CN, COOH, COO—(C
1
-C
6
)-alkyl, CO—NH
2
, NH
2
, NH—(C
1
-C
6
)-alkyl, N—[(C
1
-C
6
)-alkyl]
2
, NCO—(C
1
-C
6
)-alkyl, NCOO—(C
1
-C
6
)-alkyl, NCOO—(C
1
-C
6
)-alkenyl, NCOO—(C
1
-C
6
)-alkynyl or NCOO—(C
1
-C
4
)-alkylene-(C
6
-C
10
)-aryl; or
 (CH
2
)
m
-aryl, where m ranges from 0-6, and aryl is phenyl, O-phenyl, CO-phenyl, benzo[1,3]dioxolyl, heterocycloalkyl, pyridyl, indolyl, piperidinyl, tetrahydronaphthyl, naphthyl, 2,3-dihydro-benzo[1,4]dioxinyl, benzo[1,2,5]thiadiazolyl, pyrrolidinyl, morpholinyl, where the aryl is unsubstituted or substituted by at least one R9;
R9 is F, Cl, Br; OH, NO
2
, CF
3
, OCF
3
, (C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl-OH, O—(C
1
-C
6
)-alkyl, S—(C
1
-C
6
)-alkyl, (C
1
-C
4
)-alkylphenyl, COOH, or COO—(C
1
-C
6
)-alkyl; and their physiologically tolerable salts.
In one embodiment, the invention further relates to the use of the compounds of the formula I
in which
A is phenyl or naphthyl, where the phenyl or naphthyl is unsubstituted or substituted 1, 2, or 3 times wherein each substituent is independently chosen from F, Cl, Br, OH, CF
3
, NO
2
, CN, OCF
3
, O—(C
1
-C
6
)-alkyl, O—(C
2
-C
6
)-alkenyl, O—(C
2
-C
6
)-alkynyl, S—(C
1
-C
6
)-alkyl, S—(C
2
-C
6
)-alkenyl, S—(C
2
-C
6
)-alkynyl, SO—(C
1
-C
6
)-alkyl, SO
2
—(C
1
-C
6
)-alkyl, SO
2
—NH
2
, (C
1
-C
6
)-alkyl, (C
2
-C
6
)-alkenyl, (C
2
-C
6
)-alkynyl, (C
3
-C
7
)-cycloalkyl, (C
3
-C
7
)-cycloalkyl-(C
1
-C
4
)-alkylene, (C
0
-C
6
)-alkylene-COOH, (C
0
-C
6
)-alkylene-COO—(C
1
-C
7
)-alkyl, (C
0
-C
6
)-alkylene-COO—(C
2
-C
7
)-alkenyl, CONH
2
, CONH—(C
1
-C
6
)-alkyl, CON—[(C
1
-C
6
)-alkyl]
2
, CONH—(C
3
-C
6
)-cycloalkyl, (C
0
-C
6
)-alkylene-NH
2
, (C
0
-C
6
)-alkylene-NH—(C
1
-C
6
)-alkyl, (C
0
-C
6
)-alkylene-N—[(C
1
-C
6
)-alkyl]
2
, NH—CO—(C
1
-C
6
)-alkyl, NH—CO-phenyl, NH—SO
2
-phenyl, wherein the phenyl of NH—CO-phenyl and NH—SO
2
-phenyl is unsubstituted or substituted 1 or 2 times wherein each substituent is independently chosen from F, Cl,

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