Drug – bio-affecting and body treating compositions – Nonspecific immunoeffector – per se ; or nonspecific... – Synthetic or structurally-modified peptidoglycan or...
Patent
1981-10-30
1983-11-08
Fan, Jane T.
Drug, bio-affecting and body treating compositions
Nonspecific immunoeffector, per se ; or nonspecific...
Synthetic or structurally-modified peptidoglycan or...
549278, 435125, 435133, C07D31178, A61K 31365
Patent
active
044142269
DESCRIPTION:
BRIEF SUMMARY
DESCRIPTION
This invention relates to new 1,4-naphthoquinone derivatives. More particularly, this invention relates to a new 1,4-naphthoquinone derivative, a salt of the carboxy group thereof, a method of production thereof, and an agent or composition containing said derivative or salt for the prophylaxis and treatment of coccidiosis.
The 1,4-naphthoquinone derivative as the subject matter compound of this invention is represented by the following general formula (I). ##STR3## (wherein R.sup.1 is hydrogen, hydroxy, lower alkoxy or arylthio; R.sup.2 is carboxy, esterified carboxy or amidated carboxy; R.sup.1 and R.sup.2, taken together, may represent a group of ##STR4## R.sup.3 is hydrogen or lower alkyl; R.sup.4 is lower alkyl; R.sup.5 is hydrogen or halogen; R.sup.6 is hydrogen, lower alkyl or lower alkanoyl).
The groups defined above will be explained below in detail. It should be understood that unless otherwise specificed, the term "lower" as used herein signifies a group containing 1 to 6 carbon atoms.
(1) R.sup.1 =lower alkoxy:
Examples of this lower alkoxy group include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy and tert-butoxy. Preferred is methoxy.
(2) R.sup.1 =arylthio:
This arylthio group is a substituted or unsubstituted arylthio group, which may for example be phenylthio, tolylthio, xylylthio, mesylthio or cumenylthio.
(3) R.sup.2 =esterified carboxy:
This esterified carboxy group may for example be a carboxy group esterified by a lower alkanol, such as lower alkoxycarbonyl (e.g. methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, etc.). Preferred is methoxycarbonyl.
(4) R.sup.2 =amidated carboxy:
This amidated carboxy group includes the amide formed between carboxy or a reactive derivative thereof and an unsubstituted or substituted amino compound. The amino compound includes not only urea, N,N-di-substituted derivatives thereof, substituted or unsubstituted aniline, and substituted alkylamino compounds of the general formula (II-1): ##STR5## (wherein R.sup.7, R.sup.8 and R.sup.9 each is hydrogen or lower alkyl), but also imide compounds. A typical imide compound is N,N'-dicyclohexylcarbodiimide. The reactive derivatives of carboxy include acid halides, acid anhydrides, active amides, active esters, etc.)
Preferred examples of the amidated carboxy group formed between carboxy and such an amino compound are carbamoyl, N-cycloalkyl-N-(N'-cycloalkylcarbamoyl)carbamoyl, N-(1-phosphonoethyl)carbamoyl, N-(1-O,O-di(lower) alkylphosphonoethyl)carbamoyl, N-phenylcarbamoyl, N-tolylcarbamoyl, N-(lower alkoxycarbonyl)phenylcarbamoyl, etc.
(5) R.sup.3, R.sup.4, R.sup.6, R.sup.7, R.sup.8, R.sup.9 =lower alkyl:
Examples of this lower alkyl group are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, sec-butyl, etc., with methyl and ethyl being especially desirable.
(6) R.sup.6 =lower alkanoyl:
Examples of this lower alkanoyl group include acetyl, propionyl, butyryl, isobutyryl, valeryl, etc., with acetyl being particularly desirable.
(7) R.sup.5 =halogen:
This halogen atom may be fluorine, chlorine, bromine or iodine, with chlorine being especially desirable.
As regards the salts of carboxy function of the final compound (I) of this invention, there may be mentioned salts with inorganic or organic cations (e.g. sodium, potassium, calcium, aluminum, ammonium, magnesium, triethylamine, ethanolamine, dicyclohexylamine, ethylenediamine, N,N'-dibenzylethylenediamine), salts with amino acids (e.g. arginine, aspartic acid, glutamic acid), etc.
The said compound (I) and said salt of carboxy function thereof can be produced in the following manner.
(I) Methods of Synthesis
(1) Synthesis of compounds (I)
(i) Process A and Process B [Synthesis of Compounds (I-A), (I-B) and (I-C)]
Among the compounds (I), compounds of the undermentioned formulas (I-A), (I-B) and (I-C) can be produced by the routes illustrated below. ##STR6## (wherein R.sup.1' is hydrogen or hydroxy; R.sup.3 and R.sup.4 ar
REFERENCES:
Neunhoeffer et al., Chem. Ber., vol. 71, 2703-2707, 1938.
Hiroichi et al., CA. 94: 63700q.
Hirokazu et al., CA. 94: 117420u.
Aoki Hatsuo
Arakawa Akira
Ikushima Koichi
Imanaka Hiroshi
Kino Eiko
Bierman Jordan B.
Bierman Linda
Fan Jane T.
Fujisawa Pharmaceutical Co. Ltd.
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