Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1998-05-18
1999-07-27
Lambkin, Deborah C.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514317, 514331, 514432, 514459, 546235, 546245, 546246, 549 13, 549 28, 549426, A61K 31445, A61K 3138, A61K 3135, C07D21132
Patent
active
059290889
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
Compounds of formula ##STR2## wherein R.sub.1 is hydrogen or a lower alkyl radical and n is 4, 5, or 6 are known in U.S. Pat. No. 4,024,175 and its divisional U.S. Pat. No. 4,087,544. The uses disclosed are: protective effect against cramp induced by thiosemicarbazide; protective action against cardiazole cramp; the cerebral diseases, epilepsy, faintness attacks, hypokinesia, and cranial traumas; and improvement in cerebral functions. The compounds are useful in geriatric patients. The patents are hereby incorporated by reference.
U.S. Pat. No. 5,270,317 and its divisional U.S. Pat. No. 5,352,788 disclose compounds of formula ##STR3## in which: R.sub.1 and R.sub.2 are similar or different and are each independently hydrogen or a group selected from a C.sub.1 -C.sub.6 alkyl, a C.sub.1 -C.sub.4 alkoxy, an amino, an aminomethyl, a carboxyl, an alkoxycarbonyl in which the alkoxy is C.sub.1 -C.sub.4, a cyano, a tetrazolyl, a methyltetrazolyl, a methylsulfonylamino, a trifluoromethylsulfonylamino, a trifluoromethylsulfonylaminomethyl, an N-cyanoacetamide, an N-hydroxyacetamide, an N-(4-carboxy-1,3-thiazol-2-yl)acetamide, a ureido, a 2-cyanoguanidinocarbonyl, a 2-cyanoguanidinomethyl, an imidazol-1-yl-carbonyl, and a 3-cyano-2-methylisothioureidomethyl, with the proviso that at least one of the substituents R.sub.1 or R.sub.2 is other than hydrogen; substituted by one or more halogen atoms, a C.sub.2 -C.sub.6 alkenyl, a C.sub.3 -C.sub.7 cycloalkyl, a phenyl, a phenylalkyl in which the alkyl is C.sub.1 -C.sub.3, or a phenylalkenyl in which the alkenyl is C.sub.2 -C.sub.3, said phenyl groups being unsubstituted, or monosubstituted or polysubstituted by a halogen atom, a C.sub.1 -C.sub.4 alkyl, a C.sub.1 -C.sub.4 halogenoalkyl, a C.sub.1 -C.sub.4 polyhalogenoalkyl, a hydroxyl, or a C.sub.1 -C.sub.4 alkoxy; and either phenyl or a phenylalkyl in which the alkyl is C.sub.1 -C.sub.3, said alkyl, phenyl, and phenylalkyl groups being unsubstituted or substituted by one or more halogen atoms or by a group selected from a C.sub.1 -C.sub.4 perfluoroalkyl, a hydroxyl, and a C.sub.1 -C.sub.4 alkoxy; R.sub.8, in which R.sub.7 is hydrogen, a C.sub.1 -C.sub.4 alkyl or a phenyl, and R.sub.8 is a C.sub.1 -C.sub.4 alkyl or a phenyl: (CH.sub.2).sub.n or a group of the formula (CH.sub.2).sub.p Y--(CH.sub.2).sub.q, in which Y is either an oxygen atom, or a sulfur atom, or a carbon atom substituted by a C.sub.1 -C.sub.4 alkyl group, a phenyl or a phenylalkyl in which the alkyl is C.sub.1 -C.sub.3, or a group N--R.sub.6, in which R.sub.6 is a hydrogen, a C.sub.1 -C.sub.4 alkyl, a phenylalkyl in which the alkyl is C.sub.1 -C.sub.3, a C.sub.1 -C.sub.4 alkylcarbonyl, a C.sub.1 -C.sub.4 alkylcarbonyl, a C.sub.1 -C.sub.4 halogenoalkylcarbonyl, a C.sub.1 -C.sub.4 polyhalogeno-alkylcarbonyl, a benzoyl, an alphaaminoacyl or an N-protecting group, or R.sub.4 and R.sub.5, together with the carbon atom to which they are bonded, form an indane or an adamantane; by one or more halogen atoms; and C.sub.3 -C.sub.7, which is unsubstituted or substituted by one or more halogen atoms: angiotension II.
J. Med. Chem., 38:3772-3779 (1995) covers the syntheses of spiropiperidines as potent and selective non-peptide tackykinin NK.sub.2 receptor antagonists.
SUMMARY
The novel cyclic amino acids, their derivatives and pharmaceutically acceptable salts are useful in a variety of disorders. The disorders include: epilepsy, faintness attacks, hypokinesia, cranial disorders, neurodegenerative disorders, depression, anxiety, panic, pain, and neuropathological disorders.
The compounds are those of formula ##STR4## or a pharmaceutically acceptable salt thereof wherein: X is O, S, S(O), S(O).sub.2, or NR.sub.1 wherein R.sub.1 is hydrogen, straight or branched alkyl of from 1 to 6 carbon atoms, or benzyl, --C(O)R.sub.2 wherein R.sub.2 is straight or branched alkyl of from 1 to 6 carbon atoms, benzyl, or phenyl, --CO.sub.2 R.sub.3 wherein R.sub.3 is straight or branched alkyl of from 1 to 6 carbon atoms, or benzyl wherein the benzyl and phe
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Smith et al., "New Spiropiperidines as Potent and Selective Non-Peptide Tachykinin NK2 Receptor Antagonists", J. Med. Chem., vol. 38, No. 19, 1995, pp. 3772-3779.
Bryans Justin S.
Horwell David C.
Kneen Clare O.
Ratcliffe Giles
Anderson Elizabeth M.
Lambkin Deborah C.
Warner-Lambert & Company
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