4-Amino-2-ureido (or -thioureido)-pyrimidine-5-carboxylic acid anilides
First Claim
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1. A 4-amino-2-ureido (or -thioureido)-pyrimidine-5-carboxylic acid anilide of the formula ##STR79## or a physiologically acceptable acid addition salt thereof, wherein X is oxygen or sulfur,R1 is hydrogen, (C1 -C3)-alkyl, or phenyl;
- R2 taken alone is hydrogen, (C1 -C10)-alkyl, (C3 -C4)-alkenyl, (C4 -C8)-cycloalkyl, phenyl, phenylalkyl having 1 or 2 carbon atoms in the alkyl portion, or is phenyl or such phenylalkyl mono- or di-substituted in the benzene ring by (C1 -C3)-alkyl, halogen, or (C1 -C4)-alkoxy, or substituted by trifluoromethyl, methoxycarbonyl, ethoxycarbonyl, or methylenedioxy;
R3 taken alone is hydrogen, (C1 -C3)-alkyl, or phenyl;
R2 and R3 taken together are --(CH═
CH)--, linear or branched (C2 -C8)-alkylene, or such alkylene substituted by (C2 -C4)-alkenyl, by phenyl, or by phenyl substituted by chlorine, bromine, methyl, ethyl, methoxy, or ethoxy;
R4 is hydrogen or (C1 -C8)-acyl;
R6 is hydrogen, (C1 -C3)-alkyl, (C3 -C4)-alkenyl, benzyl, phenyl, benzyl mono- or di-substituted in the benzene ring by chlorine or methoxy, or phenyl substituted by methyl, chlorine, or by methyl and chlorine;
R7 taken alone is hydrogen, (C1 -C3)-alkyl, (C3 -C4)-alkenyl, (C5 -C6)-cycloalkyl, phenyl, halogen, trifluoromethyl, (C1 -C4)-alkylthio, (C1 -C2)-alkoxycarbonyl, cyano, acetamino, amino, nitro, carboxyl, (C1 -C4)-alkoxy or ##STR80## wherein Z is oxygen, sulfur, ##STR81## --CH2 --, or --CH2 CH2 --, and R9 and R10, which are the same or different, are hydrogen, fluorine, chlorine, bromine, (C1 -C3)-alkyl, (C1 -C2)-alkoxy, acetamino, (C1 -C2)-alkoxycarbonyl, or carbonyl;
R8 is fluorine, chlorine, bromine, methyl, (C1 -C2)-alkoxy, or trifluoromethyl;
n is 0, 1, 2, or 3;
and if n is 1, thenR7 and R8, taken together, may be methylenedioxy or ethylenedioxy.
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Abstract
What is disclosed are 4-amino-2-ureido (or -thioureido)-pyrimidine-5-carboxylic acid anilides of the formula ##STR1## further defined in the specification, and physiologically acceptable acid addition salts thereof, methods for treating adiposity and disturbances of the lipometabolism with these compounds or salts, and pharmaceutical compositions containing these compounds or salts and useful for inducing anorexia or affecting the lipometabolism.
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Citations
9 Claims
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1. A 4-amino-2-ureido (or -thioureido)-pyrimidine-5-carboxylic acid anilide of the formula ##STR79## or a physiologically acceptable acid addition salt thereof, wherein X is oxygen or sulfur,
R1 is hydrogen, (C1 -C3)-alkyl, or phenyl; -
R2 taken alone is hydrogen, (C1 -C10)-alkyl, (C3 -C4)-alkenyl, (C4 -C8)-cycloalkyl, phenyl, phenylalkyl having 1 or 2 carbon atoms in the alkyl portion, or is phenyl or such phenylalkyl mono- or di-substituted in the benzene ring by (C1 -C3)-alkyl, halogen, or (C1 -C4)-alkoxy, or substituted by trifluoromethyl, methoxycarbonyl, ethoxycarbonyl, or methylenedioxy; R3 taken alone is hydrogen, (C1 -C3)-alkyl, or phenyl; R2 and R3 taken together are --(CH═
CH)--, linear or branched (C2 -C8)-alkylene, or such alkylene substituted by (C2 -C4)-alkenyl, by phenyl, or by phenyl substituted by chlorine, bromine, methyl, ethyl, methoxy, or ethoxy;R4 is hydrogen or (C1 -C8)-acyl; R6 is hydrogen, (C1 -C3)-alkyl, (C3 -C4)-alkenyl, benzyl, phenyl, benzyl mono- or di-substituted in the benzene ring by chlorine or methoxy, or phenyl substituted by methyl, chlorine, or by methyl and chlorine; R7 taken alone is hydrogen, (C1 -C3)-alkyl, (C3 -C4)-alkenyl, (C5 -C6)-cycloalkyl, phenyl, halogen, trifluoromethyl, (C1 -C4)-alkylthio, (C1 -C2)-alkoxycarbonyl, cyano, acetamino, amino, nitro, carboxyl, (C1 -C4)-alkoxy or ##STR80## wherein Z is oxygen, sulfur, ##STR81## --CH2 --, or --CH2 CH2 --, and R9 and R10, which are the same or different, are hydrogen, fluorine, chlorine, bromine, (C1 -C3)-alkyl, (C1 -C2)-alkoxy, acetamino, (C1 -C2)-alkoxycarbonyl, or carbonyl; R8 is fluorine, chlorine, bromine, methyl, (C1 -C2)-alkoxy, or trifluoromethyl; n is 0, 1, 2, or 3; and if n is 1, then R7 and R8, taken together, may be methylenedioxy or ethylenedioxy. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9)
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Specification
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Current AssigneeHoechst Aktiengesellschaft (Sanofi )
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Original AssigneeHoechst Aktiengesellschaft (Sanofi )
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InventorsGranzer, Ernold, Kampe, Klaus-Dieter
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Primary Examiner(s)Coughlan, Jr., Paul M.
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Application NumberUS06/101,160Time in Patent Office627 DaysField of Search544/324, 544/325, 544/122, 424/251US Class Current514/275CPC Class CodesA61P 3/04 Anorexiants; Antiobesity ag...A61P 3/06 AntihyperlipidemicsC07C 255/00 Carboxylic acid nitriles cy...C07D 239/48 Two nitrogen atoms
