Phenylethyl and phenylpropylamines

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...

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514210, 514212, 514327, 514328, 514330, 514409, 514423, 514424, 514425, 514613, 514617, 514623, 514624, 540450, 540451, 540526, 540531, 540607, 546216, 546219, 546226, 548408, 548540, 548546, 548550, 548953, 564123, 564181, 564185, 564188, 564190, C07C23262, C07C23714, C07C23716, C07C23704

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active

056936303

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/SE94/00860, filed Sep. 16, 1994.


FIELD OF THE INVENTION

The present invention relates to novel, phenylethylamines and phenylpropylamines, and processes for their preparation, pharmaceutical compositions containing the phenylethylamines and phenylpropylamines and the use of said compounds in therapy.
The object of the present invention is to provide novel compounds that will be useful in the treatment of psychiatric disorders such as schizophrenia and other psychoses, anxiety, depression and manic-depressive psychosis.


PRIOR ART

The French patent application M 7.430 describes compounds of the formula ##STR3## wherein X is a hydrogen or chlorine atom. The compounds have neurosedative and spasmolytic effects.
From the U.S. Pat. No. 4,833,138 compounds of the formula ##STR4## are known.
According to the patent each of R.sup.1 and R.sup.2 is one or more groups independently selected from hydrido, hydroxyalkyl, haloalkyl acyl, cykloalkyl, cycloalkylalkyl, haloalkylsulfonyl, alkylcarbonyl, halo, alkylthio, phenylalkyl, phenylalkylthio, cyano, nitro, amino, alkylamino, sulfono, alkylaminosulfonyl, amido, alkylamido, hydroxyimino, hydroxyiminoalkyl, carboxyl, carboxylalkyl, carboxylalkenyl, thiazolyl, methylthiazolyl, alkoxycarbonylamino, alkylaminosulfonylamino, aminocarbonyliminoalkyl, haloalkylcarbonyl, morpholinoalkylcarbonyl, aminothiazolyl, morpholinothiocarbonylalkyl, dioxycycloalkylalkyl, cyclopropylcarbonyl, tetrazolylalkyl, iminoalkyl and hydroxyiminoalkyl; wherein each of R.sup.3 through R.sup.6 is independently selected from hydrido, alkyl, alkoxy, alkenyl, hydroxyalkyl, alkylaminoalkylcarbonyl, alkoxyalkyl, glycyl, aminoalkyl, alkylaminothioalkyl, aminoalkylcarbonyloxy, cyano, phenylalkyl, phenylalkyloxyalkyl, cycloalkyl, haloalkyl, morpholinoalkylalkyl, piperazinylalkyl, azepinylalkyl, phenylalkylaminoalkylamido, alkylaminocarbonyloxyalkyl, piperidinylalkyl and piperidinylalkylaminoalkylcarbonyl; wherein X is selected from sulfur, sulfinyl and sulfonyl; wherein m is zero or one; and wherein n is an integer from one through five.
The compounds have effect on the prevention of neurodegenerative consequences associated with conditions of hypoxia or ischemia.
Furthermore it is known from the French patent M 7.644 that the compounds of the formula ##STR5## wherein R represents a group ##STR6## and R' and R" represent a smaller alkyl preferably methyl, or together form a second bond --CH.sub.2 --CH.sub.2 -- between the two nitrogen atoms. The compounds have spasmolytic effect.
In the Journal of Medicinal Chemistry, 1989, 32, 1921-1926, Glennon and coworkers describe some compounds of the formula ##STR7## wherein X is hydrogen or methoxy, n is 2 or 3, R' is methyl or hydrogen affinity for the 5-HT.sub.1A receptor.
In Bull. Chim. Soc. Fr. 1975, (3-4, Pt.2), 846-9 some compounds of the formula ##STR8## are described. These compounds are used as intermediates in the preparation of 8,13-diazasteroids.
In Khim. Geterotsikl. Soedin. 1986, (4), 514-17 (CA 106 (15): 119843z) some compounds of the formula ##STR9## are described, These compounds are used as starting material in the synthesis of 1-aralkyl-4-acyl-2-piperazinones.


DISCLOSURE OF THE INVENTION

According to the present invention it has been found that new compounds of the general formula I ##STR10## or pharmaceutically acceptable salts thereof, wherein Z is a saturated or unsaturated 3 to 6 carbon chain, group, position of the phenyl ring and are the same or different and selected from the following groups: H, OH, OR.sub.14, halogen, CO.sub.2 R.sub.9, CN, CF.sub.3, NO.sub.2, NH.sub.2, COCH.sub.3,OSO.sub.2 CF.sub.3,OSO.sub.2 CH.sub.3,CONR.sub.10 R.sub.11, OCOR.sub.12, wherein R.sub.9, R.sub.12 and R.sub.14 is a straight or branched C.sub.1-4 alkyl group, R.sub.10 and R.sub.11 are the same or different and represents hydrogen or a straight or branched C.sub.1-6 alkyl group, ##STR11## wherein R.sub.4 and R.sub.5 are the same or different, and, when different represent a hydrogen atom, a straight or branched C.sub.1-5 a

REFERENCES:
patent: 3712924 (1973-01-01), Kruger et al.
patent: 3948898 (1976-04-01), Kutter et al.
patent: 4021558 (1977-05-01), Kutter et al.
patent: 4490369 (1984-12-01), Reiffen et al.
patent: 4855302 (1989-08-01), Gasc et al.
Redeuilh et al., Chemical Abstracts, vol. 83, abstract 97690, 1975.
Hocquaux et al., Chemical Abstracts, vol. 100, abstract 103716, 1983.
Podona et al., "Synthese de N-(2-Hydroxyethyl)iminoglutarimides a partir de N-(2-Bromoethyl)glutarimides," Tetrahedron, vol. 49, No. 21, pp. 4619-4626 (1993).
Chemical Abstracts, vol. 55, "17634g hydroxyanthranilic Acid: A Potent Inhibitor of 3-Hydroxyanthranilic Acid Oxidase," Archives of Biochemistry and Biophysics, vol. 203, No. 1, pp. 161-166 (1980).

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