Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1994-06-02
1995-10-24
Springer, David B.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
549453, 514428, 514461, C07D30128, C07D20718, A61K 31365, A61K 3140
Patent
active
054611580
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
This invention offers novel compounds which are useful for treatment of diseases such as immunodeficiency and autoimmune diseases caused by various immune disorders, and synthetic intermediates therefor.
BACKGROUND ART
Recently, many studies have been performed on mechanisms and therapeutic agents for diseases caused by various immune disorders or immune depression caused by adverse reactions of carcinostatic drugs. It is known that thymulin, a nonapeptide produced in the thymus, forms a complex with zinc and improves a depressed immunity. It is suggested that it could be an effective drug on immunodeficiency and autoimmune diseases (Med. Oncol. & Tumor Pharmacother. 6, 25-29, 1989).
However, there remain many problems in the practical use of thymulin. For example, the availability of thymulin is limited due to a small yield in the thymus and duration of the activity thereof is short because thymulin is easily decomposed by endogenous enzymes.
Therefore, synthetic compounds are desired which have a long lasting activity and can be prepared in a large amount. But few studies have been performed on such synthetic compounds having thymulin-like activities.
The inventors focused on the action mechanisms of thymulin forming a complex with zinc and studied to synthesize various novel compounds having sulfur atoms in the side chains.
The inventors also examined the effect of the obtained novel compounds. As the result of the precise studies, the inventors found that lactone or lactam compounds having sulfur atoms in the side chains showed excellent thymulin-like activities. Although many studies have been performed on lactone or lactam compounds, few compounds having sulfur atoms in the side chains were known. As mentioned later, the structural characteristic of the compounds of this invention of the formula [I] is that two intramolecular sulfur atoms exist in the side chains of lactone or lactam compounds. Such lactone or lactam compounds have not been reported.
DESCRIPTION OF THE INVENTION
This invention relates to a compound of the formula [I] and salts thereof; and a synthetic intermediate represented by the formula [II] and salts thereof, ##STR2## wherein R.sup.1 and R.sup.2 are the same or different and each is hydrogen or lower alkyl; alkyl, carboxy or lower alkoxycarbonyl; alkyl, lower alkenyl, lower alkanoyl, phenyl lower alkyl, phenylcarbonyl, trityl or tetrahydropyranyl, and the phenyl ring of the said phenyl lower alkyl or phenylcarbonyl can be substituted by lower alkyl, lower alkoxy, halogen, carboxy or lower alkoxycarbonyl; phenyl lower alkoxy, and said alkyl group can be substituted by carboxy, lower alkoxycarbonyl, amino, lower alkylamino, lower alkoxycarbonylamino or phenyl lower alkylamino, and the phenyl ring of the said phenyl lower alkyl, phenyl lower alkoxy or phenyl lower alkylamino can be substituted by lower alkyl, lower alkoxy, halogen, carboxy or lower alkoxycarbonyl, and
The same shall be applied hereinafter.
The groups defined above are explained as follows in more detail.
The term "lower alkyl" intends to designate straight or branched alkyl having 1 to 6 carbon atoms exemplified by methyl, ethyl, propyl, hexyl, iso-propyl and t-butyl.
The term "lower alkenyl" intends to designate straight or branched alkenyl having 2 to 6 carbon atoms containing double bond exemplified by vinyl, allyl and hexenyl.
The term "lower alkanoyl" intends to designate straight or branched alkanoyl having 2 to 6 carbon atoms exemplified by acetyl, propionyl, hexanoyl, iso-propionyl and pivaloyl. The term "lower alkoxy" intends to designate straight or branched alkoxy having 1 to 6 carbon atoms exemplified by methoxy, ethoxy, propoxy, hexyloxy, iso-propoxy and t-butoxy. The term "lower alkylene" intends to designate straight or branched alkylene having 1 to 6 carbon atoms exemplified by methylene, ethylene, trimethylene, tetramethylene, hexamethylene, (dimethyl)methylene and (diethyl) methylene. The term "halogen" intends to designate fluorine, chlorine, bromine and iodine.
Exam
REFERENCES:
patent: 4613613 (1986-09-01), Oguri et al.
patent: 5292767 (1994-03-01), Mita et al.
patent: 5350860 (1994-09-01), Mita et al.
Bach et al., "Thymulin, A Zinc-Dependent Hormone", vol. 6, No. 1, pp. 25-29, 1989, Med. Oncol. & Tumor Pharmacother.
Kawashima Yoichi
Mita Shiro
Nakata Katsuhiko
Santen Pharmaceutical Co. Ltd.
Springer David B.
LandOfFree
Substituted butaneolides and butane lactams, and pharmaceutical does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Substituted butaneolides and butane lactams, and pharmaceutical , we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Substituted butaneolides and butane lactams, and pharmaceutical will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1887764