Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1986-12-16
1989-08-22
Schwartz, Richard A.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
546193, 546281, 546289, 546297, 546304, 546307, 546310, 546312, 544 586, 544 60, 544124, 544360, 540597, 540604, 5142222, 5142278, 514252, 514318, 514343, 514352, 514355, 514344, A61K 3155, C07D21389
Patent
active
048596639
DESCRIPTION:
BRIEF SUMMARY
The preparation of substituted 3-nitro(and cyano)-4-aminopyridines which have bronchospasmolytic activity is described in German Offenlegungsschrift 2,900,504. However, the corresponding pyridine 1-oxides are not described in this printed publication. U.S. Patent 3,547,935 relates to 3-nitropyridines which have herbicidal activity, the definition of substituents to describe the general structural formula embracing, inter alia, 2,6-dialkyl-4-di-alkylamino-3-nitropyridine 1-oxides without, however, compounds of this type being disclosed by means of examples or by naming. Furthermore, the two German Offenlegungsschriften 3,209,274 and 3,209,276 describe 3-pyridinecarboxylic esters and 3,5-pyridinedicarboxylic esters having a substituent, bonded via a carbon atom, in the 4position, which are said to be suitable for the treatment of disorders caused by ischemia and/or hypoxia. Furthermore, the literature discloses 3-phenoxypyridine and derivatives (J.Med.Chem. 24, 346 11981) and Belgian Patent 876,389) and 2-cyano-3-phenoxypyridine 1-oxides (sic) (U.S. Pat. Nos. 4,187,379 and 4,229,457), which are attributed with antiamnesic properties.
It has now been found, surprisingly, that by the introduction of an oxygen atom in the 1-position of pyridine derivatives of the structural type described in German Offenlegungsschrift 2,900,504 there are obtained new compounds which no longer show bronchospasmolytic activity but have other valuable pharmacological properties. Of these, the principal is a pronounced cerebroprotective action which is accompanied by effects inhibiting platelet aggregation and antiedematous effects. The compounds according to the invention are in this respect considerably superior to the compounds of the other literature citations which have been mentioned as the state of the art, of which representative agents have likewise been included in the pharmacological investigation, since the known compounds have proved to be considerably less active or even inactive. Furthermore, the compounds according to the invention are also suitable as starting materials for the preparation of other valuable drugs.
Consequently, the present invention relates to new, multiply substituted pyridine 1-oxides, including the relevant salts, to a process for their preparation, to medicaments containing them, in particular those which allow prophylactic and curative treatment of brain disorders caused by vascular and degenerative factors, and to the use of the pyridine 1-oxides of the formula I and/or of the salts for the preparation of medicaments which are meant for the prevention and treatment of brain disorders caused by vascular and degenerative factors.
Thus, the subject matter is the substituted pyridine 1oxides of the formula I (see claim 1) in which
represent straight-chain or branched alkyl having 1
to 6, preferably having 1 to 3, carbon atoms, in particular methyl, 4-position, a five- to seven-membered saturated heterocyclic ring which has up to 2 heteroatoms, the second heteroatom being oxygen, sulfur which can carry up to two oxygen atoms, or nitrogen in the form of the NR.sup.6 group, in which R.sup.6 is hydrogen, alkyl having up to 2 carbon atoms, phenylalkyl having up to 2 carbon atoms in the alkyl moiety or phenyl, and the phenyl rings in the two latter radicals can carry up to two identical or different substituents from the group comprising halogen and methoxy, and which ring is unsubstituted or carries up to two identical or different substituents from the group comprising hydroxy and alkyl having up to 2 carbon atoms, and R.sup.5 represents the amino, hydroxyl or an alkoxy group having 1 to 4 carbon atoms,
R.sup.1 and R.sup.2 together preferably do not contain more than 8, and in particular not more than 6, carbon atoms. In R.sup.4 the mercaptoalkyl radical preferably contains up to 2 carbon atoms. The alkyl radical in the ring formed of R.sup.3 and R.sup.4 and in the phenylalkyl radical can contain one or two carbon atoms, and the halogen on the phenyl ring can be, in particular, fluorine, chlorine or
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patent: 3547935 (1970-12-01), Diehl et al.
patent: 4067874 (1978-01-01), Ursprung
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Arznieum.-Forsch. (Drug. Res.) 24, No. 12 (1974), pp. 1964-1970.
Patents Abstracts of Japan, vol. 8, No. 260, 1984, Pat. No. 58-13201.
German Search Report.
Elben Ulrich
Greve Wilfried
Rudolph Karl
Schindler Ursula
Hoechst Aktiengesellschaft
Northington Zinna
Schwartz Richard A.
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