Amino acid derivatives

Details Amino acid derivatives Amino acid derivatives

1991-07-12

1993-05-25

Lee, Mary C.

Organic compounds -- part of the class 532-570 series

Organic compounds

Esters having the thiocarboxylate group, -cx-, wherein the...

558250, 558251, 558254, 560 16, 560153, 562426, 562556, 564153, 564154, C07C32720, C07C32122, C07C32914

Patent

active

052141810

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

This invention offers novel compounds which are useful for treatment of various diseases such as immunodeficiency and autoimmune diseases caused by immune disorders.


BACKGROUND ART

Recently there are many studies on mechanisms and therapeutic agents for various diseases caused by immune disorders and immune depression due to side effects of carcinostatic agents. It is known that thymulin, nonapeptide produced in thymus, shows a recovering effect for depressed immunity by conforming a complex with zinc. Therefore, thymulin has a possibility to be applied for treatment of immunodeficiency and autoimmune diseases. But there are many unclear points about the actions of thymulin, and few studies on synthetic compounds showing thymulin-like effects have been made.
Thymulin is a very small amount substance produced in thymus and easily decomposed by enzyme existing in living body because thymulin is a natural product. Therefore, there are many problems to apply thymulin to clinical use. Considering the action mechanism of thymulin, namely thymulin shows effects by conforming a complex with zinc, we synthesized various amino acid derivatives having sulfur atoms and examined the effects thereof comparing with thymulin.


DISCLOSURE OF THE INVENTION

This invention relates to a compound of the formula [I] and salts thereof, ##STR2## wherein R.sup.1 and R.sup.2 are the same or different and each is hydrogen, lower alkyl, lower alkanoyl, phenylcarbonyl, phenyl lower alkyl or phenyl lower alkoxycarbonyl, and said phenyl ring of phenylcarbonyl, phenyl lower alkyl or phenyl lower alkoxycarbonyl can be substituted by lower alkyl, hydroxy, lower alkoxy or halogen; ##STR3## or --COR.sup.7 ; R.sup.5 and R.sup.6 are the same or different and each is hydrogen, lower alkyl, lower alkanoyl, lower alkoxycarbonyl, phenylcarbonyl, phenyl lower alkyl, phenyl lower alkoxycarbonyl or ##STR4## and said phenyl ring of phenylcarbonyl, phenyl lower alkyl or phenyl lower alkoxycarbonyl can be substituted by lower alkyl, hydroxy, lower alkoxy or halogen; alkylene; and
The terms 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, isopropyl and t-butyl. The term "lower alkanoyl" intends to designate straight or branched alkanoyl having 2 to 6 carbon atoms exemplified by acetyl, propionyl, hexanoyl, isopropionyl and t-butanoyl. The term "lower alkoxy" intends to designate straight or branched alkoxy having 1 to 6 carbon atoms exemplified by methoxy, ethoxy, propoxy, hexyloxy, isopropoxy and t-butoxy. The term "halogen" intends to designate fluorine, chlorine, bromine and iodine.
The "salt" means a pharmaceutically acceptable salt with organic acid or base, or inorganic acid or base. Examples of such salts are hydrochloric acid salt, hydrobromic acid salt, sulfuric acid salt, phosphoric acid salt, lactic acid salt, maleic acid salt, fumaric acid salt, oxalic acid salt, methanesulfonic acid salt, p-toluenesulfonic acid salt, sodium salt, potassium salt, calcium salt, magnesium salt, zinc salt, ammonium salt, triethanolamine salt and dicyclohexylamine salt.
The compounds of this invention can be prepared by the following methods. ##STR5## The compound of the formula [II] is condensed with the compound of the formula [III] to give the compound of the formula [I] using a condensing agent such as N,N'-dicyclohexylcarbodiimide which is widely used for peptide synthesis. such as acid chloride, acid anhydride, mixed acid anhydride and active ester, and reacted with the compound of the formula [III] to give the compound of the formula [I].
The above methods are widely used for peptide synthesis and it is not necessary to specify the reaction condition. ##STR6##
The compound of the formula [I] can be prepared by a reaction of the compound of the formula [V] with the compound of the formula [VI] by the similar method as shown in the part 1).
The compound of the formula [V] can be prepared by

REFERENCES:
patent: 4847200 (1989-07-01), Wolfe et al.
Stedman's Medical Dictionary, 23rd Ed., Williams & Wilkins Company, Baltimore, p. 31, (1970).
Bach, et al., Bulletin de L'Institut Pasteur, 1978, pp. 325-398.
Bach, et al., Med. Oncol. & Tumor Pharmacother, vol. 6, No. 1, pp. 25-29, 1989.
Helv. Chim. Acta, 67 (3), 870-5 (1984), James A. Shields et al.

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