The present disclosure pertains to a process for preparing hydroxyethylethyleneamines, ethyleneamines, or mixtures thereof, and/or ethylene urea derivatives thereof. The process includes reacting diethanolamine with an amine-functional compound that includes at least two —NH— units of which at least one is selected from the group of primary amine groups and cyclic secondary amine groups. The amine-functional compound includes at least one —NH—CH2-CH2-NH— unit wherein one or more —NH—CH2-CH2-NH— units in the amine-functional compound may be present in the form of cyclic ethylene urea moieties, piperazine moieties, or linear ethylene urea moieties, in the presence of a carbon oxide delivering agent.

Methods are provided for manufacturing a cyclic urea adduct of an ethyleneamine compound, the ethyleneamine compound being selected from the group of ethyleneamines and hydroxyethylethyleneamines and comprising at least one —NH—CH2-CH2-NH— moiety and at least two ethylene moieties, wherein the ethyleneamine compound is reacted with CO2 in the presence of an auxiliary compound selected from ethylenediamine (EDA), monoethanolamine (MEA) and mixtures thereof, the molar ratio of auxiliary compound to amine compound being at least 0.02:1. It has been found that the presence of an auxiliary compound selected from ethylenediamine (EDA), monoethanolamine (MEA) and mixtures thereof leads to a substantial increase of the reaction rate as compared to a process wherein the auxiliary compound is not present.

Methods are provided for manufacturing a cyclic urea adduct of an ethyleneamine compound, the ethyleneamine compound being selected from the group of ethyleneamines and hydroxyethylethyleneamines and comprising at least one —NH—CH2-CH2-NH— moiety and at least two ethylene moieties, wherein the ethyleneamine compound is reacted with CO2 in the presence of an auxiliary compound selected from ethylenediamine (EDA), monoethanolamine (MEA) and mixtures thereof, the molar ratio of auxiliary compound to amine compound being at least 0.02:1. It has been found that the presence of an auxiliary compound selected from ethylenediamine (EDA), monoethanolamine (MEA) and mixtures thereof leads to a substantial increase of the reaction rate as compared to a process wherein the auxiliary compound is not present.

A compound comprises at least one cyclic urea moiety including a head portion and a tail portion connected through an amide moiety or a cyclic amidine moiety, wherein the head portion comprises a polyalkylenepolyamine structure comprising 3 to 10 C2-C4 alkylene moieties present between nitrogen atoms, wherein the alkylene moieties may be the same or different and may be substituted with one or more C1 to C3 alkyl groups, wherein at least one of the alkylene moieties together with its adjoining nitrogen atoms is in the form of a cyclic alkylene urea moiety of the formula

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wherein A is a C2 to C4 alkylene moiety which may be substituted with one or more C1 to C3 alkyl groups and wherein the tail portion includes an alkyl or alkenyl group with 6 to 24 carbon atoms which may be substituted.

A compound comprises at least one cyclic urea moiety including a head portion and a tail portion connected through an amide moiety or a cyclic amidine moiety, wherein the head portion comprises a polyalkylenepolyamine structure comprising 3 to 10 C2-C4 alkylene moieties present between nitrogen atoms, wherein the alkylene moieties may be the same or different and may be substituted with one or more C1 to C3 alkyl groups, wherein at least one of the alkylene moieties together with its adjoining nitrogen atoms is in the form of a cyclic alkylene urea moiety of the formula

##STR00001##

wherein A is a C2 to C4 alkylene moiety which may be substituted with one or more C1 to C3 alkyl groups and wherein the tail portion includes an alkyl or alkenyl group with 6 to 24 carbon atoms which may be substituted.

A process is provided for preparing ethyleneamines of the formula NH.sub.2—(C.sub.2H.sub.4—NH—).sub.pH wherein p is at least 3, or derivatives thereof wherein one or more units —NH—C.sub.2H.sub.4—NH— may be present as a cyclic ethylene urea unit or piperazine unit or between two units —NH—C.sub.2H.sub.4—NH— a carbonyl moiety is present. The process includes reacting an ethanolamine-functional compound OH—(C.sub.2H.sub.4—NH—).sub.qH wherein q is at least 2, an amine-functional compound NH.sub.2—(C.sub.2H.sub.4—NH—).sub.rH wherein r is at least 1, in the presence of a carbon oxide delivering agent, wherein the molar ratio of ethanolamine-functional compound to amine-functional compound is from about 0.05:1 to about 0.7:1 and the molar ratio of carbon oxide delivering agent to amine-functional compound is higher than the molar ratio of ethanolamine-functional compound to amine-functional compound, provided that the process does not comprise reacting 3 moles of ethylenediamine (EDA) and 1 mole of AEEA (aminoethylethanolamine) in the presence of 1.65 moles of urea at 280 deg C. for 2 hours.

A process is provided for preparing ethyleneamines of the formula NH.sub.2—(C.sub.2H.sub.4—NH—).sub.pH wherein p is at least 3, or derivatives thereof wherein one or more units —NH—C.sub.2H.sub.4—NH— may be present as a cyclic ethylene urea unit or piperazine unit or between two units —NH—C.sub.2H.sub.4—NH— a carbonyl moiety is present. The process includes reacting an ethanolamine-functional compound OH—(C.sub.2H.sub.4—NH—).sub.qH wherein q is at least 2, an amine-functional compound NH.sub.2—(C.sub.2H.sub.4—NH—).sub.rH wherein r is at least 1, in the presence of a carbon oxide delivering agent, wherein the molar ratio of ethanolamine-functional compound to amine-functional compound is from about 0.05:1 to about 0.7:1 and the molar ratio of carbon oxide delivering agent to amine-functional compound is higher than the molar ratio of ethanolamine-functional compound to amine-functional compound, provided that the process does not comprise reacting 3 moles of ethylenediamine (EDA) and 1 mole of AEEA (aminoethylethanolamine) in the presence of 1.65 moles of urea at 280 deg C. for 2 hours.

The application discloses pharmaceutical compounds of formula I useful for treating CNS diseases wherein m, s, R.sup.1 R.sup.5, R.sup.6 and R.sup.7 are as defined herein.

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The application discloses pharmaceutical compounds of formula I useful for treating CNS diseases wherein m, s, R.sup.1 R.sup.5, R.sup.6 and R.sup.7 are as defined herein.

##STR00001##

Methods are provided for manufacturing a cyclic urea adduct of an ethyleneamine compound, the ethyleneamine compound being selected from the group of ethyleneamines and hydroxyethylethyleneamines and comprising at least one —NH—CH2-CH2-NH— moiety and at least two ethylene moieties, wherein the ethyleneamine compound is reacted with CO2 in the presence of an auxiliary compound selected from ethylenediamine (EDA), monoethanolamine (MEA) and mixtures thereof, the molar ratio of auxiliary compound to amine compound being at least 0.02:1. It has been found that the presence of an auxiliary compound selected from ethylenediamine (EDA), monoethanolamine (MEA) and mixtures thereof leads to a substantial increase of the reaction rate as compared to a process wherein the auxiliary compound is not present.