Abstract: The present invention relates to a diamine compound represented by the general formula (1), a ruthenium-diamine complex, an iridium-diamine complex, and a rhodium-diamine complex having the diamine compound as a ligand. Furthermore, the present invention relates to methods for selectively producing optically active compounds by using any of these complexes as a catalyst. wherein R1, R2, R3, X, Y, and Z are as defined in claim 1.

Abstract: A novel method for producing a stereoselective epoxyketone compound is provided. A method for producing an epoxyketone compound represented by the formula (1), as represented by the following scheme, whereby it is possible to obtain an epoxyketone derivative in good yield and at high selectivity and to provide an industrially useful production method and an intermediate thereof. wherein R1 is a hydrogen atom, a linear, branched or cyclic alkyl group, an aromatic group which may have a substituent, or a heterocyclic group which may have a substituent, and R2 is a protective group for an amino group. R is a hydrogen atom or a C1-10 alkyl group, and R's may be the same or different, provided that at least one R is a C1-10 alkyl group.

Abstract: The present application provide processes for the preparation of fingolimod and its pharmaceutically acceptable salts, process for the purification of fingolimod hydrochloride and process for the preparation of amorphous fingolimod hydrochloride.

Abstract: A new class of compounds, namely diamino alcohols, is described, along with a process for their production and their use as dispersing additives for coating formulations.

Abstract: The present invention relates to improved processes for the production of 2-amino-2-[2-(4-C2-20 alkyl-phenyl)ethyl]propane-1,3-diols, and to compounds for use therein.

Abstract: Disclosed is a method of making a 2-substituted-1,4-benzenediamine by nucleophilic aromatic substitution.

Abstract: The present invention relates to processes for the preparation of (2-Amino-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol hydrochloride (Fingolimod) and pharmaceutically acceptable salts thereof, and intermediates formed in such processes.

Abstract: The object of the present invention is a new process for the synthesis of tapentadol, both as free base and in hydrochloride form, which comprises the step of alkylation of the ketone (VII) to yield the compound (VIII), as reported in Diagram 1, with high stereoselectivity due to the presence of the benzyl group as substituent of the amino group. It was surprisingly found that this substitution shifts the keto-enol equilibrium towards the desired enantiomer and amplifies the capacity of the stereocenter present in the compound (VII) to orient the nucleophilic addition of the organometallic compound at the carbonyl towards the desired stereoisomer. This substitution thus allows obtaining a considerable increase of the yields in this step, and consequently allows significantly increasing the overall yield of the entire tapentadol synthesis process. A further object of the present invention is constituted by the tapentadol free base in solid form, obtainable by means of the process of the invention.

Abstract: The present invention relates to an improved process for the preparation of (2R,3R)-3-(3-methoxyphenyl)-N,N,2-trimethylpentanamine which is an intermediate for the preparation of the analgesic tapentadol.

Abstract: The present invention relates to an improved process for the preparation of 3-[(1R,2R)-3-(dimethylamino)-1-ethyl-2-methylpropyl]phenol monohydrochloride.

Abstract: The present invention relates to an improved process for the preparation of (2R,3R)-3-(3-methoxyphenyl)-N,N,2-trimethylpentanamine which is an intermediate for the preparation of the analgesic tapentadol.

Abstract: A new class of compounds, namely diamino alcohols, is described, along with a process for their production and their use as dispersing additives for coating formulations.

Abstract: Disclosed is a preparation method which makes it possible to produce an aminoalcohol derivative having a high optical purity and to enable the large scale synthesis thereof at a low price. For instance, a compound represented by the following general formula (8) is recrystallized in the course of the production process thereof: In this case, R1 represents, for instance, a trihalomethyl group; R2 represents, for instance, a hydrogen atom; R3 represents, for instance, a halogen atom; R4 represents, for instance, a lower alkyl group; X represents, for instance, a sulfur atom; n represents an integer ranging from 1 to 4; and W represents hydrogen chloride or hydrogen bromide.

Abstract: The present invention relates to improved processes for the production of 2-amino-2-[2-(4-C2-20-alkyl-phenyl)ethyl]propane-1,3-diols, and to compounds for use therein.

Abstract: A process is disclosed for the preparation of a compound of formula and/or an addition salt of a proton acid, wherein R1 and R2 independently represent alkyl, cycloalkyl, aryl or aralkyl, each aryl or aralkyl being optionally further substituted with alkyl, alkoxy and/or halogen. The process involves reacting a mixture comprising a methyl ketone of formula and a compound of formula H2N—R2 (V) and/or an addition salt of proton acid, and formaldehyde in the presence of a solvent selected from the group consisting of water, aliphatic alcohols, cycloaliphatic alcohols and mixtures thereof, and optionally a proton acid to afford a ?-amino ketone of formula and/or an addition salt of a proton acid, and reducing the carbonyl group of said ?-amino ketone to afford a compound of formula I, and/or an addition salt of a proton acid wherein the first step is carried out at a pressure above 1.5 bar.

Abstract: The present invention relates to an improved, process for large scale production of 1-[2-(dimethylamino)-1-(4-phenol)ethyl]cyclohexanol (O-desmethylvenlafaxine) or its pharmaceutically acceptable salts with increased yield and minimal impurities.

Abstract: The present invention describes processes for the preparation of O-desmethylvenlafaxine and tridesmethylvenlafaxine, which may be used as an intermediate in preparing O-desmethylvenlafaxine.

Abstract: The invention relates to substituted 1-aryl-but-3-enylamine and 1-aryl-but-2-enylamine compounds, to a method for the production thereof, to medicaments containing said compounds and to their use in the production of medicaments.

Abstract: A process for making optically pure (R) and (S) salbutamol comprises obtaining the (R) or (S) isomer of either salbutamol or a salbutamol precursor in substantially optically pure form by resolving a racemic or optically impure mixture of enantiomers of salbutamol or of said precursor with either (L) or (D) tartaric acid, and where necessary converting said isomer of said precursor into either (R or (S) salbutamol respectively; then optionally converting said optically pure (R) and/or (S) salbutamol into a pharmaceutically acceptable salt.

Abstract: Disclosed are multibinding compounds which are ?2 adrenergic receptor agonists and are useful in the treatment and prevention of respiratory diseases such as asthma, bronchitis. They are also useful in the treatment of nervous system injury and premature labor.

Abstract: A process for producing an optically active amino alcohol is provided that includes a step in which a nitro ketone or a cyano ketone is reacted with a hydrogen-donating organic or inorganic compound in the presence of a transition metal compound catalyst having an optically active nitrogen-containing compound as an asymmetric ligand to give an optically active nitro alcohol or an optically active cyano alcohol, and a step in which the above optically active alcohol is further reduced to efficiently produce an optically active amino alcohol.

Abstract: Disclosed is a process for the production of 2-amino-2-[2-(4-C2-20-alkyl-phenyl)ethyl]propane-1,3-diols.

Abstract: Disclosed is a process for the production of 2-amino-2-[2-(4-C2-20-alkyl-phenyl)ethyl]propane-1,3-diols.

Abstract: 1-phenyl-3-dimethylaminopropane compounds corresponding to the formula I a method of preparing them, and the use of these substances as analgesic active ingredients in pharmaceutical compositions.

Abstract: A synthesis of fluoxetine is disclosed. The process begins with a lower alkyl ester of 3-benzoylpropionic acid, which is reduced in the presence of a chiral ligand to produce the corresponding .gamma.-hydroxy ester, and the ester is cleaved. The free acid is then condensed with the alcohol to form a .gamma.-lactone, which is treated with ammonia to provide the .gamma.-hydroxy amide. The amide undergoes a Hoffman rearrangement to provide a 2-oxo-1,3 oxazine, which is reduced to 3-(methylamino)-1-phenyl-1-propanol. The alcohol is deprotonated and reacted with a 4-chloro- or 4-fluoro benzotrifluoride to provide fluoxetine free base.

Abstract: A synthesis of fluoxetine is disclosed. The process begins with a lower alkyl ester of 3-benzoylpropionic acid, which is reduced in the presence of a chiral ligand to produce the corresponding .gamma.-hydroxy ester, and the ester is cleaved. The free acid is then condensed with the alcohol to form a .gamma.-lactone, which is treated with ammonia to provide the .gamma.-hydroxy amide. The amide undergoes a Hoffman rearrangement to provide a 2-oxo-1,3 oxazine, which is reduced to 3-(methylamino)-1-phenyl-1-propanol. The alcohol is deprotonated and reacted with a 4-chloro- or 4-fluoro benzotrifluoride to provide fluoxetine free base.

Abstract: The present invention relates to a method of forming a 1,3-diamino-3-substituted-2-propanol chemical intermediate from which various chemicals, such as selected protease-inhibitors and other drugs, as well as polymers, can be synthesized.This method includes contacting a nitromethyl amino acid compound with at least one reducing agent to form the 1,3-diamino-3-substituted-2-propanol chemical intermediate.

Abstract: The present invention relates to a method of forming a 1,3-diamino-3-substituted-2-propanol chemical intermediate from which various chemicals, such as selected protease-inhibitors and other drugs, as well as polymers, can be synthesized.This method includes contacting a nitromethyl amino acid compound with at least one reducing agent to form the 1,3-diamino-3-substituted-2-propanol chemical intermediate.

Abstract: The present invention relates to a method of forming a 1,3-diamino-3-substituted-2-propanol chemical intermediate from which various chemicals, such as selected protease-inhibitors and other drugs, as well as polymers, can be synthesized.The method includes contacting a nitromethyl amino acid compound with at least one reducing agent to form the 1,3-diamino-3-substituted-2-propanol chemical intermediate.

Abstract: Disclosed herein is a stereospecific synthesis amenable to the large scale preparation of a hydrochloric acid addition salt of a chlorohydrin of the formula ##STR1## wherein R.sup.1 and R.sup.2 are amino protective groups and R.sup.3 is an amino acid side chain or a protected amino acid side chain. The synthesis involves reacting an aldehyde of the formula ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 are as defined hereinbefore with (chloromethyl)lithium at -20.degree. C. or below and contacting the resulting diastereoisomeric mixture of lithium alcoholates with aqueous hydrochloric acid to obtain a separable mixture of the hydrochloric acid addition salts of the chlorohydrin and its corresponding hydroxy diastereoisomer. The hydrochloric acid addition salt of the chlorohydrin is transformed readily into corresponding optionally amino-protected aminoepoxides; for example, 3(S)-(tert-butyloxycarbonylamino)-l,2(S)-epoxy-4-phenyl-butane.

Abstract: The invention relates to a method for producing albuterol by the resolution of a mixture of enantiomers of methyl 5-[2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl]-2-(phenylmethoxy)benzoate or .alpha.-[[(1,1-dimethylethyl)amino]methyl]-4-(phenylmethoxy)-1,3-benzenedi methanol using a chiral acid such as (+/-) di-toluoyltartaric acid or (+/-) di-benzoyltartaric acid.

Abstract: A process is described for the preparation of (+)-2-(3,4-dichlorophenyl)-4-hydroxybutylamine (I) by reaction of 3,4-dichlorophenylacetonitrile (II) with an alkali metal halogenoacetate, treatment of the 3-cyano-3-(3,4-dichlorophenyl)propionic acid (III) with D-(-)-N-methylglucamine, with second-order asymmetric conversion, hydrolysis of the D-(-)-N-methylglucamine salt of (-)-3-cyano-3-(3,4-dichlorophenyl)propionic acid and enantioconservative reduction of the resulting levorotatory cyanoacid with a borane.

Abstract: 3-Substituted para-aminophenols of general formula: ##STR1## where X=H, halogen; Y=O--, --S--; R=alkyl, hydroxyalkyl, C.sub.1-4 aminoalkyl or C.sub.3 -C.sub.6 polyhydroxyalkyl;with the proviso that, when X=H, R is not methyl, and when X=H and Y=O, R is not ethyl;process for preparing them, intermediate compounds of formula: ##STR2## where X.sub.1 =halogen, Y and R have the meaning stated above; with the proviso that, when Y=O, R is not methyl, and when R=aminoalkyl, X.sub.1 can also denote hydrogen;dyeing compositions containing one or more compounds of formula (I), and a process For dyeing human hair.

Abstract: A catalytic asymmetric reduction process, which, by hydrogenating trisubstituted olefins, yields a corresponding organic compound having a high level of enantiomeric purity is disclosed. The process is also effective for the catalytic asymmetric reduction of certain enamines and related compounds to yield a corresponding amine or related compound, respectively, having a high level of enantiomeric purity. The reduction process utilizes a chiral metal catalyst that includes a metal or metal complex that is selected from groups 3, 4, 5, or 6, lanthanides and actinides. Moreover, the process uses hydrogen as the stoichiometric reducing agent and may be carried out at pressures ranging from about 0.5 to 200 atmospheres. The reaction can also be carried out using an acidic compound as a rate enhancing additive.

Abstract: A catalytic asymmetric reduction process, which, by hydrogenating enamines, yields a corresponding amine having a high level of enantiomeric purity is disclosed. The reduction process utilizes a chiral metal catalyst that includes a metal or metal complex that is selected from groups 3, 4, 5, or 6, lanthanides and actinides. Moreover, the process uses hydrogen as the stoichiometric reducing agent and may be carried out at pressures ranging from about 0.5 to 200 atmospheres.

Abstract: The present invention relates to a method of forming a 1,3-diamino-3-substituted-2-propanol chemical intermediate from which various chemicals, such as selected protease-inhibitors and other drugs, as well as polymers, can be synthesized.This method includes contacting a nitromethyl amino acid compound with at least one reducing agent to form the 1,3-diamino-3-substituted-2-propanol chemical intermediate.

Abstract: A method for the enantioselective reduction of an .alpha.-iminoketone to an .alpha.-aminoalcohol is disclosed. The method utilizes a borane reducing agent as the reducing agent and a chiral 1,3,2-oxazaborole as the catalyst. The method is applied to the synthesis of R-albuterol from methyl 5-acetylsalicylate in high yield and high optical purity.

Abstract: The present invention is concerned with the preparation of N-substituted vicinal aminoalcohol derivatives from the corresponding hydroxyl-protected cyanohydrin derivatives by successive partial reduction, transimination using a primary amine, reduction of the resulting imine and optional removal of the hydroxyl-protecting group. The products are obtained either as a racemate or in an optically pure form, depending upon the stereochemical composition of the starting cyanohydrin derivatives.The present invention is also concerned with certain new enantiomerically pure hydroxyl-protected vicinal aminoalcohols.

Abstract: The invention relates to a method for producing albuterol by the resolution of a mixture of enantiomers of 5-[2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl]-2-hydroxybenzoate using ditoluoyltartaric acid.

Abstract: 3-Substituted para-aminophenols, process for preparing them, their use for dyeing keratinous fibres and the intermediate compounds used in the process of preparation.3-Substituted para-aminophenols, of general formula: ##STR1## where X.dbd.H, halogen; Y.dbd.O--, --S--; R.dbd.alkyl, hydroxyalkyl, C.sub.1-4 aminoalkyl or C.sub.3 -C.sub.6 polyhydroxyalkyl;with the proviso that, when X.dbd.H, R is not methyl, and when X.dbd.H and Y.dbd.O, R is not ethyl;process #or preparing them, intermediate compounds of formula: ##STR2## where X.sup.1 .dbd.halogen, Y and R have the meaning stated above; with the proviso that, when Y.dbd.O, R is not methyl, and when R.dbd.aminoalkyl, X.sub.1 can also denote hydrogen;dyeing compositions containing one or more compounds of formula (I), and a process for dyeing human hair.

Abstract: Intermediates and a process for their preparation are disclosed which are useful for the preparation of a renin inhibiting compound of the formula: ##STR1## wherein R is a nitrogen-containing heterocycle which is bonded via a nitrogen atom to the sulfonyl group, R.sub.6 is hydrogen, alkoxy, halogen or loweralkyl, R.sub.7 is loweralkyl having 2 to 7 carbon atoms, and R.sub.8 is loweralkyl, cycloalkyl, or aryl or a pharmaceutically acceptable acid addition salt thereof.

Abstract: The invention relates to a method of preparing optically active alcohols which consist substantially (at least 75% e.e.) or entirely of one enantiomer of formula 4 ##STR1## wherein R and A are as defined therein. The method comprises, which maintaining enantiomeric excess, converting an optically active cyanohydrin of formula 1 ##STR2## into optically active protected cyanohydrin of formula 2 ##STR3## converting the protected cyanohydrin of formula 2 into an optically active compound of formula 3 ##STR4## removing the protecting group B.

Abstract: A process is provided for catalytically reducing imines, oximes, hydrazones and related compounds. Moreover, there is provided a process for the catalytic asymmetric reduction of imines, oximes, hydrazones, and the like, using enantiomerically enriched catalysts, to provide chiral amine reaction products which are enriched in one enantiomer. Catalytic asymmetric reduction can also be carried out using an achiral precatalyst in combination with aThe U.S. Government has rights in this invention pursuant to NIH Grant Number GM 34917.

Abstract: A method of preparing an .alpha.-d-phenylalkylbenzyl carbinol by the reaction of a phenylbenzyl ketone with an alkali metal enolate of an amide to form an aldol adduct, which is reduced and purified to form an .alpha.-d-phenylalkylbenzyl carbinol, wherein the carbinol so produced possesses analgesic activity. In an embodiment of the invention, a phenylbenzyl ketone is reacted with an alkali metal enolate of an amide to form an aldol adduct, which is reacted with an alkali metal salt of a secondary amine to form a dianion; the dianion is alkylated with an alkyl halide to form an .alpha.-isomer of an aldol adduct, which is reduced and purified to form an .alpha.-d-phenylalkylbenzyl carbinol possessing analgesic activity.

Abstract: The invention relates to a method for the preparation of an .alpha.,.alpha.-disubstituted .alpha.-amino alcohol from the corresponding amide with the aid of sodium in the presence of an alcohol as solvent. The conversion of amino acid amide to amino alcohol proceeds virtually quantitatively. Moreover, the reduction of the amino acid amide to the corresponding amino alcohol proceeds with retention of optical activity.

Abstract: A process for the preparation of phenylethanolaminotetralins of formula ##STR1## wherein X is hydrogen, a halogen, a trifluoromethyl or a lower alkyl group and R.sup.o is hydrogen or a methyl group substituted by a carboxy or a lower carbalkoxy group, which comprises treating a mandelic acid with a 2-amino-7-hydroxytetralin, optionally alkylating with a lower alkyl haloacetate and reducing the amido group of the mandelamide into a methyleneamino group. The mandelamides intermediates are novel.

Abstract: A process for the preparation of phenylethanolaminotetralins of formula ##STR1## wherein X is hydrogen, a halogen, a trifluoromethyl or a lower alkyl group and R.degree. is hydrogen or a methyl group substituted by a carboxy or a lower carbalkoxy group, which comprises treating a mandelic acid with a 2-amino-7-hydroxytetralin, optionally alkylating with a lower alkyl haloacetate and reducing the amido group of the mandelamide into a methyleneamino group. The mandelamides intermediates are novel.

Abstract: The present invention is concerned with the preparation of erythro N-substituted vicinal aminoalcohol derivatives from hydroxyl-protected cyanohydrin derivatives by successive Grignard reaction, transimination using a primary amine, reduction of the resulting imine and removal of the hydroxyl-protecting group. The products are obtained either as a racemate or in an optically pure form, depending upon the stereochemical composition of the cyanohydrin derivatives.

Abstract: The present invention is concerned with the preparation of erythro N-substituted vicinal aminoalcohol derivatives from hydroxyl-protected cyanohydrin derivatives by successive Grignard reaction, transimination using a primary amine, reduction of the resulting imine and removal of the hydroxyl-protecting group. The products are obtained either as a racemate or in an optically pure form, depending upon the stereochemical composition of the cyanohydrin derivatives.

Abstract: A process for making optically pure (R) and (S) salbutamol comprises obtaining the (R) or (S) isomer of either salbutamol or a salbutamol precursor in substantially optically pure form by resolving a racemic or optically impure mixture of enantiomers of salbutamol or of said precursor with either (L) or (D) tartaric acid, and where necessary converting said isomer of said precursor into either (R or (S) salbutamol respectively; then optionally converting said optically pure (R) and/or (S) salbutamol into a pharmaceutically acceptable salt.