Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1995-02-09
1996-04-02
Richter, Johann
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
548178, 544368, 544238, 544333, 514254, 514210, 514218, 514253, 514255, 514256, 540470, 540553, 540575, 549435, A61K 31425, C07D27764, C07D41714, C07D41712
Patent
active
055040985
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/JP94/0071 filed Jan. 20, 1994.
TECHNICAL FIELD
The present invention relates to a novel benzothiazolesulfonaimde derivative, a method for preparing the same, and a pharmaceutical use thereof.
BACKGROUND ART
In International Patent Application Publication No. W092/14712, there is disclosed a benzothiazolesulfonylaminoethyl derivative, more specifically, 1- 2-(6-benzothiazolesulfonylamino)ethyl!-4- 3-(phenoxy)propyl!piperazine, which has the ability to relax a bronchial smooth muscle by its antihistaminic activity. However, there is no description teaching or suggesting that the above-mentioned benzothiazolesulfonylaminoethyl derivative has a protein kinase inhibiting activity.
DISCLOSURE OF THE INVENTION
In a living body, various types of protein kinases, such as protein kinase C, cyclic AMP-dependent kinase, cyclic GMP-dependent kinase and myosin light chain kinase, are present. With respect to the inhibitors for the above protein kinases, there have been proposed and expected various uses, such as a drug for circulatory organ diseases and a carcinostatic agent. Recently, it has been strongly desired to provide a compound having other protein kinase inhibiting activity as compared to the protein kinase inhibiting activities of the known protein kinase inhibitors.
The present inventors have made extensive and intensive studies with a view toward developing a compound which exhibits an excellent protein kinase inhibiting activity. As a result, it has been found that a specific benzothiazolesulfonamide derivative which is represented by the formula (I) described below has an excellent activity to inhibit protein kinase C and myosin light chain kinase. Based on the above finding, the present invention has been completed.
According to one aspect of the present invention, there is provided a benzothiazolesulfonamide derivative represented by the formula (I) or a pharmaceutically acceptable acid addition salt thereof ##STR2## wherein A represents a C.sub.2-6 alkylene group which is unsubstituted or substituted with a C.sub.1-4 alkyl group; R.sup.1 represents a hydrogen atom or a C.sub.1-4 alkyl group; each of R.sup.2 and R.sup.3 independently represents a hydrogen atom or a C.sub.1-6 alkyl group, or R.sup.2 and R.sup.3 are bonded to each other to form a C.sub.1-4 alkylene group which is unsubstituted or substituted with a C.sub.1-4 alkyl group; and R.sup.4 represents a hydrogen atom, a C.sub.1-6 alkyl group, an amidino group, or a group represented by the formula (II) ##STR3## wherein B represents a C.sub.1-6 alkylene group which is unsubstituted or substituted with a C.sub.1-4 alkyl group; and each of R.sup.5 and R.sup.6 independently represents a hydrogen atom, a C.sub.1-6 alkyl group, a C.sub.1-6 alkoxy group or a halogen atom, or R.sup.5 and R.sup.6 are bonded to each other to form a methylenedioxy group.
According to another aspect of the present invention, there is provided a method for preparing a benzothiazolesulfonamide derivative represented by the formula (I) as mentioned above or a pharmaceutically acceptable acid addition salt thereof, which comprises reacting, in an inert solvent, a compound represented by the formula (III) ##STR4## wherein X represents a halogen atom, and R.sup.1 has the same meaning as defined for the formula (I) above, ##STR5## wherein A R.sup.2, R.sup.3 and R.sup.4 have the same meanings as defined for the formula (I) above.
According to a further aspect of the present invention, there is provided a reagent for the treatment and prevention of asthma, having a protein kinase inhibiting activity, which comprises, as an active ingredient, a benzothiazolesulfonamide derivative represented by the formula (I) as mentioned above or a pharmaceutically acceptable acid addition salt thereof.
According to still a further aspect of the present invention, there is provided a pharmaceutical composition comprising a benzothiazolesulfonamide derivative represented by the formula (I) as mentioned above or a pharmaceutically acceptable acid addition salt
REFERENCES:
patent: 3852298 (1974-12-01), Wagner et al.
patent: 5326870 (1994-07-01), Kajihara et al.
Morikawa, et al., J. Med. Chem. (1989), 32, 42-46.
Cremlyn et al., Phos. Sulf. Silicon (1992), 73(1-4), 107-120.
Kajihara Akiro
Tsuchiya Masahiko
Asahi Kasei Kogyo Kabushiki Kaisha
Cross Laura R.
Richter Johann
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