Organic compounds -- part of the class 532-570 series – Organic compounds – Nitrogen attached directly or indirectly to the purine ring...
Reexamination Certificate
1999-12-03
2001-01-09
Shah, Mukund J. (Department: 1611)
Organic compounds -- part of the class 532-570 series
Organic compounds
Nitrogen attached directly or indirectly to the purine ring...
C544S398000
Reexamination Certificate
active
06172228
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a process for preparing a piperazinesulfonamide derivative and a pharmaceutically acceptable salt thereof. More specifically, the present invention relates to a process for preparing a piperazinesulfonamide derivative and a pharmaceutically acceptable salt thereof which have excellent antiallergic activity and thereby are useful as a medicament for preventing and treating diseases such as bronchial asthma, allergic rhinitis, atopic dermatitis, urticaria and the like.
2. Discussion of the Related Art
Conventionally, as processes for preparing a piperazinesulfonamide derivative, there have been known, for instance, process A, process B and process C which are described in WO95/19345 Pamphlet.
However, since the reaction processes of process A and process C are long, and the yield of the piperazinesulfonamide derivative is low, it cannot be said that these processes are industrially advantageous. In addition, since process B requires a long period of time for completion of the reaction, and the yield is not a satisfactory level, it cannot be said that process B is industrially advantageous.
Therefore, recently, it has been required to develop a process capable of industrially advantageously preparing a piperazinesulfonamide derivative in a short period of time and at high yield.
In view of the above prior art, the present invention has been accomplished, and an object of the present invention is to provide a process for efficiently and industrially advantageously preparing a piperazinesulfonamide derivative and a pharmaceutically acceptable salt thereof.
These and other objects of the present invention will be apparent from the following description.
SUMMARY OF THE INVENTION
In sum, the present invention pertains to:
(1) a process for preparing a piperazinesulfonamide derivative represented by the general formula (III):
wherein R
1
is hydrogen atom, a straight or branched chain alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen atom, hydroxyl group, trifluoromethyl group, nitro group or amino group; R
2
is a phenyl group which may have as substituents on its phenyl ring 1 to 3 groups selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen atom, hydroxyl group, trifluoromethyl group, nitro group and amino group, 2-pyridyl group, 3-pyridyl group or 4-pyridyl group; each of R
3
and R
4
is independently hydrogen atom, a straight or branched chain alkyl group having 1 to 6 carbon atoms, a hydroxyalkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, or a phenyl group which may have as substituents on its phenyl ring 1 to 3 groups selected from the group consisting of an alkyl group having 1 to
4
carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen atom, hydroxyl group, trifluoromethyl group, nitro group and amino group; and Y is an alkylene group having 1 to 12 carbon atoms,
characterized by reacting a piperazine derivative represented by the general formula (I):
wherein R
1
and R
2
are as defined above, with a halogenoalkylsulfonamide derivative represented by the general formula (II):
wherein R
3
, R
4
and Y are as defined above; and X is chlorine atom, bromine atom or iodine atom, in the presence of an organic base and in the absence of a solvent; and
(2) a process for preparing a pharmaceutically acceptable salt of a piperazinesulfonamide derivative represented by the general formula (III):
wherein R
1
is hydrogen atom, a straight or branched chain alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen atom, hydroxyl group, trifluoromethyl group, nitro group or amino group; R
2
is a phenyl group which may have as substituents on its phenyl ring 1 to 3 groups selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen atom, hydroxyl group, trifluoromethyl group, nitro group and amino group, 2-pyridyl group, 3-pyridyl group or 4-pyridyl group; each of R
3
and R
4
is independently hydrogen atom, a straight or branched chain alkyl group having 1 to 6 carbon atoms, a hydroxyalkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, or a phenyl group which may have as substituents on its phenyl ring 1 to 3 groups selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen atom, hydroxyl group, trifluoromethyl group, nitro group and amino group; and Y is an alkylene group having 1 to 12 carbon atoms,
comprising the step of preparing the piperadinesulfonamide derivative represented by the general formula (III) by the process according to item (1) above.
DETAILED DESCRIPTION OF THE INVENTION
As mentioned above, the process for preparing a piperazinesulfonamide derivative of the present invention is characterized by reacting a piperazine derivative represented by the general formula (I):
wherein R
1
is hydrogen atom, a straight or branched chain alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen atom, hydroxyl group, trifluoromethyl group, nitro group or amino group; and R
2
is a phenyl group which may have as substituents on its phenyl ring 1 to 3 groups selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen atom, hydroxyl group, trifluoromethyl group, nitro group and amino group, 2-pyridyl group, 3-pyridyl group or 4-pyridyl group, with
a halogenoalkylsulfonamide derivative represented by the general formula (II):
wherein each of R
3
and R
4
is independently hydrogen atom, a straight or branched chain alkyl group having 1 to 6 carbon atoms, a hydroxyalkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, or a phenyl group which may have as substituents on its phenyl ring 1 to 3 groups selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen atom, hydroxyl group, trifluoromethyl group, nitro group and amino group; X is chlorine atom, bromine atom or iodine atom; and Y is an alkylene group having 1 to 12 carbon atoms, in the presence of an organic base and in the absence of a solvent.
In the piperazine derivative represented by the general formula (I), R
1
is hydrogen atom, a straight or branched chain alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen atom, hydroxyl group, trifluoromethyl group, nitro group or amino group; and R
2
is a phenyl group which may have as substituents on its phenyl ring 1 to 3 groups selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen atom, hydroxyl group, trifluoromethyl group, nitro group and amino group, 2-pyridyl group, 3-pyridyl group or 4-pyridyl group.
In R
1
, the straight or branched chain alkyl group having 1 to 6 carbon atoms includes methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, neopentyl group, tert-pentyl group, n-hexyl group, isohexyl group, sec-hexyl group, neohexyl group and tert-hexyl group.
The alkoxy group having 1 to 4 carbon atoms includes methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, and the like.
The halogen atom includes fluorine atom, chlorine atom, bromine atom and iodine atom.
Among R
1
, hydrogen atom, a straight or branched chain alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen atom, hydroxyl group, trifluoromethyl group, nitro group or amino group is preferable, and hydrogen atom or a halogen atom is more preferable, and a halogen a
Kashima Kenichi
Kawanishi Kenji
Ohta Yoichiro
Sakamoto Yasuhiko
Takemura Shigetaka
Azwell Inc.
Birch & Stewart Kolasch & Birch, LLP
Liu Hong
Shah Mukund J.
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