Urea derivatives, methods for preparing ethylene amines, and methods of polymer manufacturing are provided. An exemplary method for preparing ethylene amines with n ethylene units and n+1 amine groups wherein n is at least 4, or urea derivatives of said ethylene amines, includes reacting an ethanolamine-functional compound, an amine-functional compound, and a carbon oxide delivering agent, wherein the ethanolamine-functional compound is of the formula HO(C2H4NH)qH, q is at least 1, the amine-functional compound is of the formula H2N(C2H4NH)rH, r is at least 1, the sum q+r is at least 4 and wherein optionally one or more of the ethanol-amine functional compound or amine-functional compound are at least partly used as their cyclic carbamate derivative, or linear or cyclic urea derivative.

Urea derivatives, methods for preparing ethylene amines, and methods of polymer manufacturing are provided. An exemplary method for preparing ethylene amines with n ethylene units and n+1 amine groups wherein n is at least 4, or urea derivatives of said ethylene amines, includes reacting an ethanolamine-functional compound, an amine-functional compound, and a carbon oxide delivering agent, wherein the ethanolamine-functional compound is of the formula HO(C2H4NH)qH, q is at least 1, the amine-functional compound is of the formula H2N(C2H4NH)rH, r is at least 1, the sum q+r is at least 4 and wherein optionally one or more of the ethanol-amine functional compound or amine-functional compound are at least partly used as their cyclic carbamate derivative, or linear or cyclic urea derivative.

A process is provided for preparing ethyleneamines of the formula NH.sub.2(C.sub.2H.sub.4NH).sub.pH wherein p is at least 3, or derivatives thereof wherein one or more units NHC.sub.2H.sub.4NH may be present as a cyclic ethylene urea unit or piperazine unit or between two units NHC.sub.2H.sub.4NH a carbonyl moiety is present. The process includes reacting an ethanolamine-functional compound OH(C.sub.2H.sub.4NH).sub.qH wherein q is at least 2, an amine-functional compound NH.sub.2(C.sub.2H.sub.4NH).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.4NH).sub.pH wherein p is at least 3, or derivatives thereof wherein one or more units NHC.sub.2H.sub.4NH may be present as a cyclic ethylene urea unit or piperazine unit or between two units NHC.sub.2H.sub.4NH a carbonyl moiety is present. The process includes reacting an ethanolamine-functional compound OH(C.sub.2H.sub.4NH).sub.qH wherein q is at least 2, an amine-functional compound NH.sub.2(C.sub.2H.sub.4NH).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 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 NHCH2-CH2-NH unit wherein one or more NHCH2-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.

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 NHCH2-CH2-NH unit wherein one or more NHCH2-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.

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##

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##

The invention provides 2-(substituted phenylhetero) aromatic formate FTO inhibitors, a preparation method thereof, and applications thereof. Specifically, disclosed in the present invention are a 2-(substituted phenylhetero) aromatic formate compound represented by the following formula (I), and a pharmaceutically acceptable salt, a hydrate or a solvate thereof, which can be used as an FTO targeting inhibitor for treating diseases associated with FTO targets, including obesity, metabolic syndrome (MS), type 2 diabetes (T2D), Alzheimer's diseases, and cancers such as breast cancers, small-cell lung cancers, human bone marrow rhabdomyosarcoma, pancreatic cancer, malignant glioblastoma and the like.

##STR00001##

In the method, a trione compound represented by the following formula (1) is (i) reduced by NaAlH.sub.2(OCH.sub.2CH.sub.2OCH.sub.3).sub.2 and subsequently further reduced by a metal borohydride salt, or (ii) reduced by calcium borohydride, thereby producing an amide alcohol compound represented by the following formula (3) (wherein, R.sup.1 and R.sup.2 may be the same or different and each represents a hydrogen atom or a protecting group of an ureylene group; R.sup.4 represents an alkyl group, an aralkyl group, or an aryl group; and each of R.sup.5, R.sup.6, and R.sup.7 represents a hydrogen atom, an alkyl group, an alkoxy group, or a halogen atom).

##STR00001##