Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1994-01-02
1996-04-09
Cintins, Marianne M.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
5142328, 544126, 546 82, A61K 3144, A61K 31535, C07D47104, C07D41314
Patent
active
055062350
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to novel quinoline derivatives that exhibit activity as immunostimulants. By improving a host's immune response, the compounds of this invention increase the host's resistance to infection or infestation by bacteria, viruses, fungi, etc. They are therefore useful, alone or in combination with anti-infective therapy, in the prophylactic or therapeutic treatment of any infectious disease.
U.S. Pat. No. 4,716,168, assigned to Norwich Eaton Pharmaceuticals, Inc. refers to other quinoline derivatives, more specifically, to imidazo(4,5-f)quinolines, and states that such compounds are useful in enhancing the immune response system of a mammal.
SUMMARY OF THE INVENTION
The present invention relates to compounds of the formula ##STR2## wherein R.sup.1 is (C.sub.3 -C.sub.18) alkyl or phenyl optionally substituted with from one to three substituents independently selected from (C.sub.1 -C.sub.6) alkyl, (C.sub.1 -C.sub.6) alkoxy, halo, cyano, (C.sub.3 -C.sub.8) cycloalkyl-(C.sub.1 -C.sub.6)alkoxy wherein the cycloalkyl moiety may be substituted with from one to three (C.sub.1 -C.sub.6)alkyl groups; hydroxyl, benzyloxy, carboxyl, hydroxy-(C.sub.1 -C.sub.6) alkyl, pyrrolidino, piperidino, morpholino and --CONHQCOOH wherein Q is (C.sub.1 -C.sub.4) alkyl; cycloalkyl, phenyl or phenyl-(C.sub.1 -C.sub.6) alkyl, wherein the phenyl moieties of said phenyl and said phenyl-(C1-C.sub.6) alkyl may be optionally substituted with from one to three substituents independently selected from (C.sub.1 -C.sub.6) alkyl, (C.sub.1 -C.sub.6)-alkoxy, halo, cyano and benzyloxy; hydroxy-(C.sub.1 -C.sub.6) alkyl, --NHC(.dbd.NR.sup.8)R.sup.9, --NHSO.sub.2 R.sup.11, --NHCOR.sup.12 or ureido; attached, form a group of the formula ##STR3## wherein the carbon of group A labelled with an asterisk (*) represents the point of attachment of R.sup.4 to the quinoline nucleus and the carbon of group A adjacent to it represents the point of attachment of R.sup.5 to the quinoline nucleus; --NHCOR.sup.13, --NHSO.sub.2 R.sup.13, or ureido; --NHSO.sub.2 R.sup.14, --NHCOR.sup.14, ureido or guanidino; (C.sub.1 -C.sub.6)alkyl; (C.sub.1 -C.sub.6) alkyl and phenyl optionally substituted with halo, (C.sub.1 -C.sub.6)alkyl or (C.sub.1 -C.sub.6)alkoxy; 6-amino-4-(m-anisidino)-2-phenylquinoline hydrochloride, 6-amino-4-cyclohexylamino-2-phenylquinoline hydrochloride, 6-amino-4-(m-anisidino)-2-methylquinoline methanesulfonate, 6-amino-4-(p-toluidino)-2-methylquinoline methanesulfonate, 9-(p-anisidino)-2-methyl-1H-pyrazolo[3,4 -f]quinoline hydrochloride, 9-(cyclohexylamino)-1H-pyrazolo[3,4-f]quinoline methanesulfonate, 9-(cyclopentylamino)-1H-pyrazolo[3,4-f]quinoline methanesulfonate, 4-(phenylamino)-2-phenylquinolin-6-ol hydrobromide; 4-(butylamino)-2-phenylquinolin-6-ol hydrobromide; 4-[(3-methoxyphenyl)amino]-2-methylquinolin-7-ol hydrochloride; 4-[(4-chlorophenyl)amino]-2-methylquinolin-7-ol hydrobromide; 4-(cyclohexylamino)-2-methylquinolin-6-ol hydrochloride; 4-[(3-methoxyphenyl)amino]quinolin-6,8-diol hydrochloride; and 4-(cyclohexylamino)quinolin-8-ol hydrochloride.
This invention also relates to the pharmaceutically acceptable acid addition salts and cationic salts of compounds of the formula I.
Unless otherwise indicated, the term "halo" as used herein, includes fluoro, chloro, bromo and iodo.
Unless otherwise indicated, the term "alkyl" as used herein, may be straight, branched or cyclic, and may include straight and cyclic moieties as well as branched and cyclic moieties.
The compounds of formula I may have chiral centers and therefore may occur in different stereoisomeric configurations. The invention includes all stereoisomers of such compounds of formula I, including mixtures thereof.
The present invention also relates to all radio-labelled forms of the compounds of the formula I. Such radio-labelled compounds are useful as research and diagnostic tools in metabolism pharmacokinetic studies and in binding assays in both animals and man.
The present invention also relates to a pharmaceutical composition for enhancing or stimul
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S. Renault et al., Recherche sur les aminoquinoleines. XVI: Alkylamino-4 quinoleines et quinaldines a longues chaines a activite amoebicide potentielle, 11, 6, European Journal of Medicinal Chemistry, 561-565 (1976).
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McFarland James W.
Moyer Mikel P.
Butterfield Garth
Cintins Marianne M.
Ginsburg Paul H.
Pfizer Inc.
Richardson Peter C.
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