Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Nitrogen containing other than solely as a nitrogen in an...
Reexamination Certificate
2002-03-29
2004-05-04
O'Sullivan, Peter (Department: 1621)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Nitrogen containing other than solely as a nitrogen in an...
C564S081000
Reexamination Certificate
active
06730704
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to 1-(aryloxy)propionoyl-2-arylsulfonyl hydrazines useful as hypoglycemic agents, and to a process for synthesis thereof The present invention also relates to the synthesis of 1-(aryloxy)propionoyl-2-arylsulfonyl hydrazines as new hypoglycemic agents which may be useful in the treatment of diabetes.
BACKGROUND OF THE INVENTION
Introduction of more clinically effective hypoglycemic agents has been followed invariably by the rapid emergence of resistant antidiabetic drugs leading to increasing demand for new and potent hypoglycemic drugs. Acquisition of resistance has seriously reduced the therapeutic value of many known drugs including antidiabetics and has become a major stimulus to look for new moieties. Hence, the best approach is to look for new molecules structurally different from the existing drugs. The present invention relates to such an effort in developing title compounds as new hypoglycemic agents. These have not so far been investigated for the hypoglycemic activity and all compounds described are new molecules reported for the first time.
Reference may be made to Indian Drugs, 17, 315, 1980, wherein, authors have synthesized arylsulfonyl hydrazines as hypoglycemic agents. The drawbacks are that no substitutions were made to the hydrazine group which can improve the hypoglycemic activity. Incorporation of aryloxyalkyl substituents to organic moieties has been found to result in compounds which possess enhanced biological profile. Reference may also be made to Indian J. Chem:27B, 1057-1059, 1988, wherein authors have introduced substitutions by condensation of 4-chlorophenoxyacetic and isobutyric acid hydrazides with arylsulfonyl chlorides.
OBJECTS OF THE INVENTION
The main object of the present invention is to provide 1-(aryloxy)propionoyl-2-arylsulfonyl hydrazines which obviates the drawbacks as detailed above.
Another object of the present invention is to provide a process for the synthesis of 1-(aryloxy)propionoyl-2-arylsulfonyl hydrazines as potential hypoglycemic agents.
Still another object of the present invention is to unravel new hypoglycemic molecules structurally different from the known drugs such as Glibenclamide, Tolbutamide, Chloropropamide, Phenformin, Metformin, etc.
SUMMARY OF THE INVENTION
In the present invention, aryloxypropionic acid hydrazides were reacted with arylsulfonyl chlorides to obtain the title compounds as hypoglycemic agents for the first time.
Accordingly the present invention relates to 1-(aryloxy)propionoyl-2-arylsulfonyl hydrazine of the formula
wherein R is selected from 4-Cl, 3-CH
3
-4-Cl and 2,4-Cl
2
, R
1
is selected from H, Cl, and CH
3
.
In another embodiment of the invention, the 1-(aryloxy)propionoyl-2-arylsulfonyl hydrazine are selected from the following
1-(aryloxy)propionoyl-2-arylsulfonyl hydrazine of the formula
1-(aryloxy)propionoyl-2-arylsulfonyl hydrazine of the formula
1-(aryloxy)propionoyl-2-arylsulfonyl hydrazine of the formula
1-(aryloxy)propionoyl-2-arylsulfonyl hydrazine of the formula
1-(aryloxy)propionoyl-2-arylsulfonyl hydrazine of the formula
1-(aryloxy)propionoyl-2-arylsulfonyl hydrazine of the formula
1-(aryloxy)propionoyl-2-arylsulfonyl hydrazine of the formula
1-(aryloxy)propionoyl-2-arylsulfonyl hydrazine of the formula
The present invention also provides a process for the synthesis of 1-(aryloxy)propionoyl-2-arylsulfonyl hydrazines useful as new oral hypoglycemic agents, which comprises reacting an aryloxypropionic acid hydrazide with an arylsulfonyl chloride.
In an embodiment of the present invention, aryloxy is selected from the group consisting of 4-chlorophenoxy, 3-methyl-4-chlorophenoxy and 2,4-dichlorophenoxy groups.
In another embodiment of the present invention, aryl is selected from the group consisting of phenyl, 4-chlorophenyl and 4-tolyl.
REFERENCES:
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Nageswar et al., Chem. Abs. 110:212780.*
D, Finley et al., “Ubiquitination” Annu. Rev. Cell Biol., vol. 7, (1991), pp. 25-69.
M. Hochstrasser, “Ubiquitin and Intracellular Protein Degradation” Current Opinion in Cell Biology, vol. 4, (1992), pp. 1024-1031.
D. Lindsey et al., “A Deubiquitinating Enzyme That Disassembles Free Polyubiquitin Chains is Required for Development But Not Growth in Dictyostelium” The Journal of Biological Chemistry, vol. 273, No. 4, Oct. 30, 1998, pp. 29178-29187.
I. Rose, “Role of Ubiquitin-Protein Isopeptidase Action in Protein Breakdown” Current Communications in Molecular Biology, (1988), Schlesinger and Hershko (eds.),Cold Spring Harbor Laboratory, New York, pp. 111-114.
Diwan Prakash Vamanrao
Raghavan Kondapuram Vijaya
Rao Adari Bhaskar
Sistla Ramakrishna
Thallapalli Ramalingam
Council of Scientific & Industrial Research
O'Sullivan Peter
Sughrue & Mion, PLLC
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