The present invention provides a novel dihydroorotic acid dehydrogenase inhibitor which is applicable to various diseases. When used as an active ingredient, a compound represented by formula (I): ##STR00001##
(wherein X represents a halogen atom, R.sup.1 represents a hydrogen atom, R.sup.2 represents an alkyl group containing 1 to 7 carbon atoms, R.sup.3 represents —CHO, and R.sup.4 represents —CH.sub.2—CH═C(CH.sub.3)—R.sup.0 (wherein R.sup.0 represents an alkyl group containing 1 to 12 carbon atoms which may have a substituent on the terminal carbon and/or on a non-terminal carbon, etc.)),
an optical isomer thereof or a pharmaceutically acceptable salt thereof has a high inhibitory effect on dihydroorotic acid dehydrogenase and can be used as an immunosuppressive agent, a therapeutic agent for rheumatism, an anticancer agent, a therapeutic agent for graft rejection, an antiviral agent, an anti-H. pylori agent, a therapeutic agent for diabetes or the like.

A method for preparing a partially fluorinated ester comprising acyl and alkoxy groups wherein the acyl group comprises a branched or linear fluorine containing C.sub.3-C.sub.8 group with one of the structures: (Formulae (I), (II)) wherein X and Y are independently selected from: —H, —CH.sub.3, —F, —Cl, —CH.sub.2F, —CF.sub.3—OCF.sub.3, —OCH.sub.2CF.sub.3, OCH.sub.2CF.sub.2CHF.sub.2 and —CH.sub.2CF.sub.3 (wherein both X and Y cannot be H) comprising reacting an unsaturated halocarbon: (Formula (III)) wherein A and B are independently selected from the group comprising —H, —CH.sub.3, —F, —Cl, —CH.sub.2F, —CF.sub.3, —OCF.sub.3, —OCH.sub.2CF.sub.3, OCH.sub.2CF.sub.2CHF.sub.2 and —CH.sub.2CF.sub.3 (wherein both A and B cannot be H) with carbon monoxide and an alcohol, in the presence of a catalyst methods.

##STR00001##

A method for preparing a partially fluorinated ester comprising acyl and alkoxy groups wherein the acyl group comprises a branched or linear fluorine containing C.sub.3-C.sub.8 group with one of the structures: (Formulae (I), (II)) wherein X and Y are independently selected from: —H, —CH.sub.3, —F, —Cl, —CH.sub.2F, —CF.sub.3—OCF.sub.3, —OCH.sub.2CF.sub.3, OCH.sub.2CF.sub.2CHF.sub.2 and —CH.sub.2CF.sub.3 (wherein both X and Y cannot be H) comprising reacting an unsaturated halocarbon: (Formula (III)) wherein A and B are independently selected from the group comprising —H, —CH.sub.3, —F, —Cl, —CH.sub.2F, —CF.sub.3, —OCF.sub.3, —OCH.sub.2CF.sub.3, OCH.sub.2CF.sub.2CHF.sub.2 and —CH.sub.2CF.sub.3 (wherein both A and B cannot be H) with carbon monoxide and an alcohol, in the presence of a catalyst methods.

##STR00001##

A method for preparing a partially fluorinated ester comprising acyl and alkoxy groups wherein the acyl group comprises a branched or linear fluorine containing C.sub.3-C.sub.8 group with one of the structures: (Formulae (I), (II)) wherein X and Y are independently selected from: —H, —CH.sub.3, —F, —Cl, —CH.sub.2F, —CF.sub.3—OCF.sub.3, —OCH.sub.2CF.sub.3, OCH.sub.2CF.sub.2CHF.sub.2 and —CH.sub.2CF.sub.3 (wherein both X and Y cannot be H) comprising reacting an unsaturated halocarbon: (Formula (III)) wherein A and B are independently selected from the group comprising —H, —CH.sub.3, —F, —Cl, —CH.sub.2F, —CF.sub.3, —OCF.sub.3, —OCH.sub.2CF.sub.3, OCH.sub.2CF.sub.2CHF.sub.2 and —CH.sub.2CF.sub.3 (wherein both A and B cannot be H) with carbon monoxide and an alcohol, in the presence of a catalyst methods.

##STR00001##

A method for preparing alkynyl 2-halo-2,2-difluoroacetate is disclosed. The method comprises: subjecting a 2-halo-2,2-difluoro acetic acid, an alkynol, and a catalyst to an esterification reaction in a solvent, to obtain alkynyl 2-halo-2,2-difluoroacetate, wherein the catalyst includes one or more of sulfuric acid, phosphoric acid and p-toluenesulfonic acid.

A method for preparing alkynyl 2-halo-2,2-difluoroacetate is disclosed. The method comprises: subjecting a 2-halo-2,2-difluoro acetic acid, an alkynol, and a catalyst to an esterification reaction in a solvent, to obtain alkynyl 2-halo-2,2-difluoroacetate, wherein the catalyst includes one or more of sulfuric acid, phosphoric acid and p-toluenesulfonic acid.

Disclosed are a process of producing a polyurethane foam product, a polyurethane foam product pre-mix, polyurethane foam product formulation, and a polyurethane foam product. The process of producing the polyurethane foam product includes contacting a halogen containing composition with a polyurethane foam product pre-mix. The polyurethane foam product pre-mix includes the halogen containing composition. The polyurethane foam product formulation includes a polyol component, an isocyanate component, and a halogen containing compound component. The polyurethane foam product is formed by the pre-mix having the halogen containing composition.

Disclosed are a process of producing a polyurethane foam product, a polyurethane foam product pre-mix, polyurethane foam product formulation, and a polyurethane foam product. The process of producing the polyurethane foam product includes contacting a halogen containing composition with a polyurethane foam product pre-mix. The polyurethane foam product pre-mix includes the halogen containing composition. The polyurethane foam product formulation includes a polyol component, an isocyanate component, and a halogen containing compound component. The polyurethane foam product is formed by the pre-mix having the halogen containing composition.

Provided is a novel compound having a selective activating effect on ERβ. The present invention provides a compound represented by the following formula (1) wherein R.sup.1 represents a cycloalkyl group having 3 to 8 carbon atoms, an alkenyl group having 2 to 6 carbon atoms and optionally substituted with a halogen atom, a 5-membered nitrogen-containing heteroaryl group, a 4- to 6-membered cyclic amino group, an alkanoylamino group having 2 to 6 carbon atoms and optionally substituted with a halogen atom, a 1-trifluoromethyl-1-hydroxymethyl group, or a 1-methylpropyl group; R.sup.2 to R.sup.5 are the same or different and each represent a hydrogen atom or a fluorine atom; and R.sup.6 represents a hydrogen atom or an alkanoyl group having 2 to 5 carbon atoms, or a salt thereof. ##STR00001##

There is provided a production method of a thiopyranose compound represented by the following Formula (2) by reacting a compound represented by the following Formula (1) with a sulfur compound. ##STR00001##
X represents a leaving group. A represents an oxygen atom or a sulfur atom. Further, each of R.sup.1A to R.sup.4B, R.sup.1B to R.sup.4B, and R.sup.5 represents a hydrogen atom or a specific substituent.