Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1992-07-29
1994-11-08
Shah, Mukund J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
540586, A61K 3155, C07D22318, C07D22332
Patent
active
053627288
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
This invention relates to 4,5-bridged-2,3,4,5-tetrahydro-1H-3-benzazepine-7-ols and derivatives and compositions and method employing such compounds.
Substituted 1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines have been described in the art. For example, see U.S. Pat. Nos. 3,393,192, 3,609,138, 4,011,319, 4,284,555 and 4,477,378 well as British Patent 1,118,688. The activities discussed for the compounds disclosed in these patents include anti-bacterial effects, central nervous system effects and hypotensive effects.
British Patent Specification No. 1 221 324 discloses compounds of the formula: ##STR3## wherein R.sub.1 and R.sub.2, independently of each other, represent a hydrogen atom, an alkyl group containing maximally 6 carbon atoms, a cycloalkyl group having from 3 to 7 carbon atoms as ring members or a phenyl group optionally substituted by a chlorine, flourine or bromine atom and/or by an alkyl group containing maximally 6 carbon atoms,
R.sub.3 and R.sub.4 have the meanings given above for R.sub.1 and R.sub.2 or together they represent a trimethylene or tetramethylene radical,
R.sub.5 represents a hydrogen or a halogen atom, and
R.sub.6 represents a hydrogen, chlorine, flourine or bromine atom, an alkyl group containing maximally 6 carbon atoms or a triflouro methyl group,
provided that no more than two of the symbols R.sub.1, R.sub.2, R.sub.3 and R.sub.4 may simultaneously represent a cycloalkyl group or an optionally substituted phenyl group. These compounds are disclosed as intermediates for the production of N-guanidinoalkyl derivatives which have antihypertensive properties, and the unsubstituted 2,3,4,5-tetrahydro-1H-3-benzazepine compound is disclosed as being useful as an intermediate for the production of arylsulphonyl ureas having a hypoglycaemic action. In addition, 7-chloro-2,3,4,5-tetrahydro-1H-3-benzazepine and the salts thereof are said to have an anorexigenic action.
WO 87/04430 and WO 89/00561 disclose compounds of the formula: ##STR4## wherein R is hydrogen, alkyl, --CH.sub.2 CH=CH.sub.2 or ##STR5## R.sup.1, R.sup.11 and R.sup.12 may be the same or different and each is hydrogen or alkyl;
Q is methylene, --O-- or --S--;
m and n are independently variable and each may have a value of 0, 1 or 2, with the provisos that the sum of m and n is not greater than 3, that m may not equal zero when Q is --O-- or --S--;
X is hydrogen, halo, alkyl, alkylthio, alkylsulfinyi, alkylsulfonyl, hydroxy, alkoxy or triflouromethyl;
Y is hydrogen, hydroxy, alkoxy, ##STR6## where R.sup.1 is as defined above;
W is hydrogen, hydroxy or alkoxy;
ring t represents a fused thiophene or fused benzene ring, said fused benzene ring optionally being substituted with a substituent Z as defined below;
R.sup.2 and R.sup.3 are independently hydrogen (provided that both are not hydrogen), alkyl, aralkyl, cycloalkyl, aryl, hydroxyalkyl, or alkoxyalkyl;
in addition, when one of R.sup.2 and R.sup.3 is as defined above, the other may be --R.sup.4 NR.sup.5 R.sup.6 {wherein R.sup.4 is alkanediyl, R.sup.5 is hydrogen or alkyl and R.sup.6 is alkyl, or R.sup.5 and R.sup.6 together with the nitrogen atom form a 1-azetidinyl, 1-pyrrolidinyl. 1-piperidinyl, 1-(4-alkylpiperazinyl), 4-morpholinyl or 1-(hexahydroazepinyl) group};
in further addition. R.sup.2 and R.sup.3 together with the nitrogen atom may form a 1-azetidinyl, 1-pyrrolidinyl, 1-piperidinyl, 4-morpholinyl, 1-(4-alkylpiperazinyl), 1-(4-alkoxyalkylpiperazinyl), 1-(4-hydroxyalkylpiperazinyl), 1-(3-hydroxyazetidinyl), 1-(3-alkoxyazetidinyl), 1-(3-hydroxypyrrolidinyl), 1-(3-alkoxypyrrolidinyl), 1-(3-or 4-hydroxypiperidinyl), 1-(3- or 4-alkoxypiperidinyl), 4-(4-oxopiperidinyl) or 1-(3-oxopyrrolidinyl) ring;
in still further addition, when R.sup.2 is hydrogen, R.sup.3 may be --CHR.sup.7 CO.sub.2 R.sup.8, wherein R.sup.7 and R.sup.8 are independently hydrogen, alkyl or aralkyl;
R.sup.9 is alkyl, aralkyl, aryl, alkoxyalkyl, aryloxyalkyl, aralkoxyalkyl, cycloalkylalkyl, alkoxycarbonylalkyl. cycloalkyl, 1-adamantyl, cycloalkoxyalkyl. alkoxy, aralkoxy, c
REFERENCES:
patent: 3393192 (1968-07-01), Walter
patent: 3609138 (1971-09-01), Mull
patent: 3752892 (1973-08-01), Hoegerle et al.
patent: 4011319 (1977-03-01), Kaiser
patent: 4284555 (1981-08-01), Gold
patent: 4477378 (1984-10-01), Gold
patent: 4973586 (1990-11-01), Berger et al.
Asberom Theodros
Berger Joel G.
Clader John W.
O'Connor Edward
Datlow Philip I.
Magatti Anita W.
Mazer Edward H.
Nelson James R.
Schering Corporation
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