Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Patent
1993-06-15
1994-10-25
Rotman, Alan L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
546 81, C07D47106, C07D48706, A61K 3150
Patent
active
053590660
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to new tricyclic compounds. More concretely, it relates to new tricyclic compounds or sales thereof which are useful as intermediates for producing synthetic microbicides excellently suitable to clinical use, and also to a process for preparing them.
Accordingly, one object of the present invention is to provide new tricyclic compounds or salts thereof which are useful as intermediates for producing synthetic microbicides excellently suitable to clinical use.
Another object of the present invention is to provide a new industrial process for preparing such tricyclic compounds or salts thereof, which is excellent in point of the yield and purity of the products.
DISCLOSURE OF THE INVENTION
New tricyclic compounds of the present invention are compounds or salts thereof which are represented by the following general formula: ##STR2## where R.sup.1 is a hydrogen atom or a carboxyl-protecting group; ##STR3## in which R.sup.4, R.sup.5 and R.sup.6 each are a hydrogen atom or a carboxyl-protecting group;
In accordance with the present invention, tricyclic compounds (A) can be prepared by the process (1) or process (2) as illustrated in the following schemes. ##STR4## or a salt thereof or a salt thereof wherein as defined above, amino group,
The starting compounds (II), (III) and (IV) can be prepared, for example, by the following processes each comprising a series of the illustrated steps. ##STR5## wherein R.sup.1, R.sup.2, R.sup.4, R.sup.5, R.sup.6, X.sup.1, X.sup.2, X.sup.3 and X.sup.5 are each as defined above,
Suitable salts of compounds (A) are both acid-addition salts thereof and base-addition salts thereof. Acid-addition salts of compounds (A) include, for example, (a) salts thereof with mineral acids such as hydrochloric acid, sulfuric acid, etc.; (b) salts thereof with organic carboxylic acids such as formic acid, citric acid, trichloroacetic acid, trifluoroacetic acid, etc.; and (c) salts thereof with sulfonic acids such as methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, mesitylenesulfonic acid, naphthalenesulfonic acid, etc. Base-addition salts of compounds (A) include, for example, (a) salts thereof with alkali metals such as sodium, potassium, etc.; (b) salts thereof with alkaline earth metals such as calcium, magnesium, etc.; (c) ammonium salts thereof; and (d) salts thereof with nitrogen-containing organic bases such as trimethylamine, triethylamine, tributylamine, pyridine, N,N-dimethylaniline, N-methylpiperidine, N-methylmorpholine, diethylamine, cyclohexylamine, procaine, dibenzylamine, 1-ephenamine, N,N'-dibenzylethylenediamine, etc.
In the above and subsequent description of this specification, suitable examples of the various definitions are explained in detail as follows:
The term "lower" is intended to mean 1 to 6, preferably 1 to 4, carbon atom(s), when the substituent is a linear or branched group; and to mean 3 to 7 carbon atoms, when it is a cyclic group.
The term "carboxyl-protecting group" indicates the ester residue of a carboxylate and is intended to mean anyone which may relatively easily be cleaved to give the corresponding free carboxyl group. Specific examples of the group include, for example, groups which may split off by treatment under mild conditions, for example, by hydrolysis or catalytic reduction, such as a lower alkyl group (e.g., methyl, ethyl, n-propyl, tert-butyl, etc.), a lower alkenyl group (e.g., vinyl, allyl, etc.), an aralkyl group (e.g., benzyl, benzhydryl, etc.), an aryl group (e.g., phenyl, etc.), etc.; and groups which may easily split off, such as a lower alkanoyloxy-lower alkyl group (e.g., acetoxymethyl, pivaloyloxymethyl, etc.), a lower alkoxycarbonyloxy-lower alkyl group (e.g., methoxycarbonyloxymethyl, 1-ethoxycarbonyloxyethyl, etc.), a lower alkoxymethyl group (e.g., methoxymethyl, etc.), a lactonyl group (e.g., phthalidyl, etc.), a boron group substituted by substituent(s) selected from a halogen atom, a lower alkanoyloxy group, a halo-(lower) alkanoyloxy group and an aroyloxy group
REFERENCES:
patent: 4762831 (1988-08-01), Grohe et al.
patent: 4801584 (1989-01-01), Yokose et al.
patent: 5254685 (1993-10-01), Yokomoto et al.
Barrett David
Inoue Satoshi
Murata Masayoshi
Sakane Kazuo
Terasawa Takeshi
Fujisawa Pharmaceutical Co. Ltd.
Rotman Alan L.
Wakunaga Pharmaceutical Co., Ltd.
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