US 2004/0176593 A1 · Hydroxyalkyl cyclic diamine compound

Abstract

The present invention is directed to a compound represented by the following formula (1) and to a process for producing a compound (5) from the compound (1). 1 By use of the compound (1) of the present invention, a variety of cyclic diamine derivatives (5) or salts thereof, useful as drugs, can be produced in an industrially advantageous manner with a constant yield.

Claims5

Dependent claims

A hydroxyalkyl cyclic diamine compound represented by the following formula (1):

7
(wherein R1 denotes a halogen atom, m is 1 or 2, and n is an integer of 1 to 6):

A process for producing a cyclic diamine derivative represented by the following formula (5) or a salt thereof:

8
(wherein A denotes NH, an oxygen atom, or a sulfur atom;
each of W1 to W4 denotes CH or any one of the W1 to W4 denotes a nitrogen atom, R2 denotes a lower alkylthio group, a mono- or di-lower-alkylamino group, a cyclic amino group, a lower alkoxy group, a halo-lower alkoxy group, or a lower alkoxy lower alkoxy group, and each of R3, R4, and R5 denotes a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxycarbonyl group, a halo-lower alkyl group, a halo-lower alkoxy group, a lower alkoxy lower alkyl group, a lower alkoxy lower alkoxy group, a hydroxy lower alkyl group, a hydroxy lower alkoxy group, a lower alkylcarbonyl group, a lower alkylthio group, a lower alkylsulfinyl group, a lower alkylsulfonyl group, a nitro group, or a cyano group, m is 1 or 2, and n is an integer of 1 to 6), characterized in that the method comprises reacting a hydroxyalkyl cyclic diamine compound represented by the following formula (1):
9
(wherein R1 denotes a halogen atom, and each of m and n has the same meaning as defined above) with R2H (wherein R2 has the same meaning as defined above), to thereby form a compound represented by the following formula (2):
10
(wherein each of R2, m, and n has the same meaning as mentioned above);
transforming the hydroxyl group of the compound represented by formula (2) into a leaving group, to thereby form a compound represented by the following formula (3):
11
(wherein X denotes a leaving group, and each of R2, m, and n has the same meaning as defined above);
and reacting the compound (3) with a thiol derivative represented by the following formula (4):
12
(wherein each of A, W1 to W4, R3, R4, and R5 has the same meaning as defined above), or reacting the compound (2) with a thiol derivative represented by the following formula (4) or (4′):
13
(wherein each of A, W1 to W4, and R3 to R5 has the same meaning as defined above) in the presence of a phosphorus compound.

12 more elements

Dependencies are inferred from the claim text.

Facts

Application

10/733,243Filed 12 Dec 2003

Priority

JP 2002-36089912 Dec 2002

Published

9 Sep 2004

Term ends

Not estimatedThe source records don’t support an estimate.

Classification11 codes

C07D 401/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links
A61P 3/06
Drugs for disorders of the metabolism: antihyperlipidemics
A61P 9/10
Drugs for disorders of the cardiovascular system: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary…
A61P 43/00
Drugs for specific purposes, not provided for in groups a61p1/00-a61p41/00

Abstract

Claims5

Dependent claims

A hydroxyalkyl cyclic diamine compound represented by the following formula (1):

7
(wherein R1 denotes a halogen atom, m is 1 or 2, and n is an integer of 1 to 6):

A process for producing a cyclic diamine derivative represented by the following formula (5) or a salt thereof:

8
(wherein A denotes NH, an oxygen atom, or a sulfur atom;
each of W1 to W4 denotes CH or any one of the W1 to W4 denotes a nitrogen atom, R2 denotes a lower alkylthio group, a mono- or di-lower-alkylamino group, a cyclic amino group, a lower alkoxy group, a halo-lower alkoxy group, or a lower alkoxy lower alkoxy group, and each of R3, R4, and R5 denotes a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxycarbonyl group, a halo-lower alkyl group, a halo-lower alkoxy group, a lower alkoxy lower alkyl group, a lower alkoxy lower alkoxy group, a hydroxy lower alkyl group, a hydroxy lower alkoxy group, a lower alkylcarbonyl group, a lower alkylthio group, a lower alkylsulfinyl group, a lower alkylsulfonyl group, a nitro group, or a cyano group, m is 1 or 2, and n is an integer of 1 to 6), characterized in that the method comprises reacting a hydroxyalkyl cyclic diamine compound represented by the following formula (1):
9
(wherein R1 denotes a halogen atom, and each of m and n has the same meaning as defined above) with R2H (wherein R2 has the same meaning as defined above), to thereby form a compound represented by the following formula (2):
10
(wherein each of R2, m, and n has the same meaning as mentioned above);
transforming the hydroxyl group of the compound represented by formula (2) into a leaving group, to thereby form a compound represented by the following formula (3):
11
(wherein X denotes a leaving group, and each of R2, m, and n has the same meaning as defined above);
and reacting the compound (3) with a thiol derivative represented by the following formula (4):
12
(wherein each of A, W1 to W4, R3, R4, and R5 has the same meaning as defined above), or reacting the compound (2) with a thiol derivative represented by the following formula (4) or (4′):
13
(wherein each of A, W1 to W4, and R3 to R5 has the same meaning as defined above) in the presence of a phosphorus compound.

12 more elements

Dependencies are inferred from the claim text.

Hydroxyalkyl cyclic diamine compound

Life of this patent

Abstract

Claims5

Hydroxyalkyl cyclic diamine compound

Life of this patent

Abstract

Claims5