Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1991-01-28
1993-02-09
Shah, Harold J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
5142355, 514252, 514318, 544131, 544295, 544360, 544365, 546193, 546194, 546296, 549292, C07D21369, C07D40106, C07D30930, A61K 3144
Patent
active
051853523
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
The compounds of formula I according to the present invention display useful pharmacological properties. In particular, they inhibit protein kinase C, a calcium- and phospholipid-dependent key enzyme, which plays a decisive part in the intracellular signal chain transduction (Y. Nishizuka, Science, 233, 305-312/1986) and is closely linked with the regulation of contractile, secretory and proliferative processes.
SUMMARY OF THE INVENTION
The invention concerns compounds of formula ##STR1## and pharmaceutically acceptable salts thereof wherein R.sup.1, R.sup.2, R.sup.3, and n are as described below.
The preferred compounds of the invention are those of formula I wherein to 22 carbon atoms or adamantylalkyl containing from 1 to 22 carbon atoms; atoms, cyclohexylmethyl, unsubstituted phenyl, phenylalkyl with from 1 to 5 carbon atoms in the straight or branched alkyl chain in which the phenyl ring is monosubstituted by halogen, hydroxyl, methyl, benzyloxy, methoxy or dimethylamino; carbon atoms in the alkyl moiety or a radical of formula III, in which R.sup.6 and R.sup.7, which are each independently hydrogen, methyl, omegahydroxypropyl or benzyl; and R.sup.10 are each independently hydrogen, methyl, benzyl or phenylethyl and k is 2, 3 or 4; hydrogen or methyl, X is an amino radical of formula VI, in which R.sup.13 is hydrogen, phenyl, phenylalkyl or diphenylalkyl with from 1 to 5 carbon atoms in the straight or branched alkyl chain and where from 1 to 3 CH-groups in the phenyl ring are substituted by nitrogen or X is formula VII, in which R.sup.14 is phenyl, R.sup.15 is cyano or aminomethyl, and p and q are each 2; and or 3.
More preferred compounds of the invention are those of formula I wherein 2-octyldecyl or adamantylethyl; methoxybenzyl, cyclohexylmethyl, dimethylaminobenzyl, dimethylaminopropyl, benzyloxybenzyl, benzyloxyphenyl, phenylethyl, hydroxybenzyl or hydroxyphenyl; and dimethylaminopropylamino, dimethylaminopropyl-N-methylamino, hydroxypropylamino, dimethylamino-N-methylamino, aminopropylamino, aminoethylamino, aminobutylamino, dimethylamino, dimethylaminopropoxy, N-benzyl-N-methylaminopropylamino, N-benzyl-N-methylamino, methoxycarbonylmethylpiperazino, benzylpiperazino, diphenylmethylpiperazino, aminomethylphenylpiperidino, phenylpiperazino, phenylethylpiperazino, pyrimidinylpiperazino or methylpiperazino.
Useful intermediate for preparing compounds of the instant invention include:
Still more preferred compounds of the instant invention are: hydrobromide, hydrobromide, hydrobromide, hydrobromide, hydrobromide, hydrobromide, hydrobromide, hydrobromide, hydrobromide, mide, drobromide, ot.hydrobromide, hydrobromide, ot.hydrobromide, idone dioxalate, idone trihydrochloride hemihydrate, 1H)-pyridone trihydrochloride, done dioxalat, trihydrochloride, trihydrochloride, trihydrochloride, dioxalate 3/4 hydrate, dioxalate hemihydrate, idone dioxalate monohydrate, done dioxalate monohydrate, hydrate, 4(1H)-pyridone difumarate, 4(1H)-pyridone difumarate 1.25 hydrate, done; diisopropyl ether, (1H)-pyridone difumarate, -4(1H)-pyridone trihydrochloride monohydrate, hemihydrate, -4(1H)-pyridone difumarate, 4(1H)-pyridone trihydrochloride hemihydrate, trihydrochloride, 4(1H)-pyridone.multidot.trihydrochloride.multidot.1/2H.sub.2 O, xy-4(1H)-pyridone, xy-4(1H)-pyridone.multidot.difumarate.multidot.2,5 H.sub.2 O, -pyridone.multidot.trihydrochloride.multidot.3/4 H.sub.2 O, H)-pyridone, hyl}-4(1H)-pyridone.multidot.trihydrochloride, -4(1H)-pyridone.multidot.dihydrochloride.multidot.2 H.sub.2 O, -4(1H)-pyridone.multidot.trihydrochloride.multidot.0,5 H.sub.2 O, ridine dihydrochloride, methyl-piperazine dihydrochloride 3/4 hydrate, (1H)-pyridone trihydrochloride, razine sesquioxalate monohydrate, multidot.dihydrochloride.multidot.H.sub.2 O, perazine, multidot.dioxalate.multidot.1/2 H.sub.2 O, perazine.multidot.trihydrochloride.multidot.1/2 H.sub.2 O, zine.multidot.dihydrochloride, tidot.trihydrochloride, thyl)piperazine.multidot.trihydrochloride 3/4 H.sub.2 O, enzylpiperazine, ylpipera
REFERENCES:
patent: 2965641 (1960-12-01), Krimmel
Imafuru et al., Bulletin of the Chemical Socity of Japan, vol. 52, No. 1, 1979, pp. 107-110.
Looker et al., Journal of Heterocyclic Chemistry, vol. 23, No. 5, 1986, pp. 5-8.
Aranda Julian
Hartenstein Johannes
Osswald Hartmut
Reck Reinhard
Rudolph Claus
Anderson Elizabeth M.
Bernhardt F.
Goedecke Aktiengesellschaft
Shah Harold J.
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