Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1997-09-23
1999-03-02
Shah, Mukund J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
544238, C07D40304, A61K 31505
Patent
active
058771751
DESCRIPTION:
BRIEF SUMMARY
This invention relates to certain 3-(pyrimidin-4-yl)-1-phenylpyridazin-4(1H)-ones, to pharmaceutical compositions containing them, to processes for their preparation and to their use in the treatment, prophylaxis and/or inhibition of seizures, neurological disorders such as epilepsy and/or conditions in which there is neurological damage such as brain trauma, cerebral ischaemia, haemorrhage, head injuries and stroke.
In particular the present invention provides compounds of formula I ##STR2## including pharmaceutically acceptable salts thereof; in which g is 0,1,2,3,4 or 5; optionally substituted by one or more substituents selected from halo, C.sub.1-4 alkyl and C.sub.1-4 alkoxy; seizures and/or neurological disorders such as epilepsy and/or conditions in which there is neurological damage such as brain trauma, cerebral ischaemia, haemorrhage, head injuries and stroke.
The compound of formula I in which g is 1, R.sub.1 is 4-fluoro and R.sub.2 is tert-butyl, namely 3-(2-tert-butylpyrimidin-4-yl)-1-(4-fluorophenyl)pyridazin-4(1H)-one, is a commercially available compound. No pharmacological activity has been disclosed for this compound and in addition there have been no disclosures of pharmaceutical compositions containing this compound.
Therefore the present invention provides novel compounds of formula I represented by formula II ##STR3## including pharmaceutically acceptable salts thereof; in which g is 0,1,2,3,4 or 5; other than tert-butyl.
Specific compounds of formula I include:
Specific compounds of formula II include:
It will be understood that any group mentioned herein containing a chain of three or more carbon atoms signifies a group in which the chain may be straight or branched. For example, an alkyl group may comprise propyl which includes n-propyl and isopropyl, and butyl which includes n-butyl, sec-butyl, isobutyl and tert-butyl. The total number of carbon atoms is specified herein for certain substituents, for example C.sub.1-4 alkyl signifies an alkyl group having from 1 to 4 carbon atoms. The term "halo" as used herein signifies fluoro, chloro, bromo and iodo. It will be appreciated that when g is 2,3,4 or 5 then R.sub.1 can represent the same halo atom or different halo atoms. It will also be understood that certain compounds of formula I or II, for example when R.sub.2 represents sec-butyl, may contain a chiral centre, and exist in different optically active forms. The present invention includes both enantiomers and mixtures of the enantiomers.
The present invention includes all salts of compounds of formula I and II which are pharmaceutically acceptable. Compounds of formula I and II may form salts with organic or inorganic acids (for example acid addition salts). Particularly suitable salts of the present invention comprise salts of acidic amino acids or suitable derivatives thereof (for example salts of glutamic acids and/or N-carbamoyl-phenylalanine), salts of suitable inorganic acids (for example salts of hydrobromic, hydrochloric, hydriodic, nitric, phosphoric, sulphonic or sulphuric acids) or salts of suitable organic acids (for example salts of acetic, alkylsulphonic, alkylsulphuric, arylsulphonic, arylsulphuric, ascorbic, benzoic, cinnamic, citric, dibenozyltartaric, dodecanoic, fumaric, gluconic, glycolic, lactic, maleic, malic, mandelic, palmitic, palmoic, pyruvic, salicylic, succinic or tartaric acids or suitable derivatives thereof). Salts include all pharmaceutically acceptable salts that may be formed from multivalent orthphosphate salts!) and all enantiomeric salts formed with pharmaceutically acceptable chiral acids or any mixtures of enantiomers of such salts (for example (+) tartrates and/or (-) tartrates). The above salts may be prepared by reacting a compound of formula I or II with suitable acids in a conventional manner.
Compounds of formula I and II and salts thereof may exist as solvates (for example if the solvent is water the hydrates may be hemihydrates, monohydrates and/or dihydrates) or as an unsolvated form (for example an anhydrous form). The degree of so
REFERENCES:
Ann. Chem. 58 (1968) pp. 128-135.
Plescia et al., J. Het. Chem. 18 (1981) pp. 333-334.
Fernandez Fernandez Maria Isabel
Heal David John
Sargent Bruce Jeremy
Knoll Aktiengesellschaft
Rao Deepak
Shah Mukund J.
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