By Direct Hydrogenation Patents (Class 564/357)
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Patent number: 8912360Abstract: Methods for preparing Ritodrine hydrochloride are provided. Also provided is non-hygroscopic, crystalline, polymorphic Ritodrine hydrochloride of Form I.Type: GrantFiled: March 24, 2011Date of Patent: December 16, 2014Assignee: Lundbeck Pharmaceuticals Italy S.p.A.Inventors: Jacopo Zanon, Giovanna Libralon, Carla De Faveri, Florian Anton Martin Huber
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Patent number: 8735627Abstract: 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.Type: GrantFiled: October 27, 2011Date of Patent: May 27, 2014Assignee: Mapi Pharma Ltd.Inventors: Ehud Marom, Michael Mizhiritskii, Shai Rubnov
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Patent number: 8618326Abstract: Disclosed is a method of making a 2-substituted-1,4-benzenediamine by nucleophilic aromatic substitution.Type: GrantFiled: January 28, 2011Date of Patent: December 31, 2013Assignee: The Procter & Gamble CompanyInventors: John Michael Gardlik, Garry Steven Garrett, Bryan Patrick Murphy, Guiru Zhang, Robert Edward Shumate, James S. Anderson
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Publication number: 20130217899Abstract: 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.Type: ApplicationFiled: October 27, 2011Publication date: August 22, 2013Applicant: MAPI PHARMA LTD.Inventors: Ehud Marom, Michael Mizhiritskii, Shai Rubnov
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Publication number: 20130123539Abstract: Methods for preparing Ritodrine hydrochloride are provided. Also provided is non-hygroscopic, crystalline, polymorphic Ritodrine hydrochloride of Form I.Type: ApplicationFiled: March 24, 2011Publication date: May 16, 2013Inventor: Jacopo Zanon
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Publication number: 20100210719Abstract: Processes for preparing desvenlafaxine and stable amorphous O-desmethylvenlafaxine succinate solid dispersions with one or more pharmaceutically acceptable carriers.Type: ApplicationFiled: July 10, 2008Publication date: August 19, 2010Applicants: DR. REDDY'S LABORATORIES LTD., DR. REDDY'S LABORATORIES, INC.Inventors: Surya Narayana Devarakonda, Sesha Reddy Yarraguntla, Venu Nalivela, Ram Thaimattam, Subbareddy Peddireddy, Balaji Raghupati, Mohammed Azeezulla Baig, Srinivas Reddy Gade, Srinivas Reddy Mallepalli, Vijaywardhan Chitta, Satyanarayana Bollikonda, Saravanan Mohanarangam, Rajasekhar Kadaboina
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Patent number: 7414153Abstract: An efficient cost-effective process for preparation of 1-erythro-2-amino-1-phenyl-1-propanol from 1-1-phenyl-1-hydroxy-2-propanone, which comprises converting 1-1-phenyl-1-hydroxy-2-propanone to 1-1-phenyl-1-hydroxy-2-propanone oxime and reducing the oxime with a catalyst consisting of finely divided nickel and aluminium metals giving good diastereomeric purity and yield.Type: GrantFiled: March 9, 2005Date of Patent: August 19, 2008Assignee: Emmellen Biotech Pharmaceuticals LimitedInventors: Subrahmanyam Gollapudy, Sunil Vaman Joshi
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Patent number: 6984738Abstract: The present invention is to provide a process for producing an optically active amino alcohol which is useful for the synthesis of natural substances and as an intermediate for drugs and agricultural chemicals in a high yield, a high selectivity and an economical manner with a good working efficiency and the present invention relates to a process for producing an optically active amino alcohol represented by the following formula (2) (in the formula, R1 is a hydrocarbon group, a substituted hydrocarbon group, an aromatic heterocyclic group, a substituted aromatic heterocyclic group, an aliphatic heterocyclic group or a substituted aliphatic heterocyclic group; R2 and R3 each independently is hydrogen atom, a hydrocarbon group, a substituted hydrocarbon group, an acyl group, an acyloxy group, an alkyloxycarbonyl group, an aralkyloxycarbonyl group, an aryloxycarbonyl group, an aromatic heterocyclic group, a substituted aromatic heterocyclic group, an aliphatic heterocyclic group or a substituted aliphatic hType: GrantFiled: October 17, 2003Date of Patent: January 10, 2006Inventors: Tohru Yokozawa, Kenji Yagi, Takao Saito
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Patent number: 6686505Abstract: 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.Type: GrantFiled: October 31, 2002Date of Patent: February 3, 2004Assignee: Kanto Kaguku Kabushiki KaishaInventors: Masahito Watanabe, Kunihiko Murata, Takao Ikariya
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Patent number: 6605744Abstract: Disclosed is a process for the production of 2-amino-2-[2-(4-C2-20-alkyl-phenyl)ethyl]propane-1,3-diols.Type: GrantFiled: May 8, 2001Date of Patent: August 12, 2003Assignees: Novartis AG, Taito Co. Ltd., Mitsubishi Pharma Corp.Inventors: Stephan Abel, Tetsuro Fujita, Ryoji Hirose, Guido Jordine, Tadashi Mishina
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Patent number: 5773469Abstract: The invention relates to diaryl antimicrobial compounds of the general formula: ##STR1## where G, E L, J, q, m, X, Ar, W, p, n and A are as described herein, pharmaceutical compositions containing the compounds, methods for their production and their use in treating bacterial infections.Type: GrantFiled: June 18, 1996Date of Patent: June 30, 1998Assignee: Ortho Pharmaceutical CorporationInventors: Ramesh M. Kanojia, James P. Demers, Dennis J. Hlasta, Sigmond G. Johnson, Dieter H. Klaubert
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Patent number: 5672706Abstract: A process is disclosed for the preparation of the substantially pure compound of the formula: ##STR1## comprising catalytic hydrogenation of a compound of the formula: ##STR2## wherein R.sub.6 and R.sub.7 are independently selected from ##STR3## wherein R.sub.a and R.sub.b are independently selected from hydrogen, loweralkyl and phenyl and R.sub.c, R.sub.d and R.sub.e are independently selected from hydrogen, loweralkyl, trifluoromethyl, alkoxy, halo and phenyl; and ##STR4## wherein the naphthyl ring is unsubstituted or substituted with one, two or three substitutents independently selected from loweralkyl, trifluoromethyl, alkoxy and halo; or R.sub.6 and R.sub.7 taken together with the nitrogen atom to which they are bonded are ##STR5## wherein R.sub.f, R.sub.g, R.sub.h and R.sub.i are independently selected from hydrogen, loweralkyl, alkoxy, halogen and trifluoromethyl; or an acid addition salt thereof.Type: GrantFiled: April 17, 1996Date of Patent: September 30, 1997Assignee: Abbott LaboratoriesInventors: Anthony R. Haight, Owen J. Goodmonson, Shyamal I. Parekh, Timothy A. Robbins, Lou S. Seif
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Patent number: 5665756Abstract: Novel aminoalkyloximes of the formula ##STR1## wherein: a. X is hydrogen, loweralkyl, loweralkoxy, halogen, trifluoromethyl, or a group of the formula ##STR2## wherein Y is hydrogen or loweralkyl, and p is 1 or 2; b. A is a group of the formula ##STR3## c. R.sup.1 and R.sup.2 are independently hydrogen or lowerakyl; and d. m is 2 to 6 and n is 0, or 2 to 6, inclusive, serotonin reuptake inhibitors, useful for treating depression and obsessive compulsive disorders are described. Also described are precursors of and processes for the preparation of such aminoakyloximes.Type: GrantFiled: August 3, 1994Date of Patent: September 9, 1997Assignee: Hoechst Marion Roussel, Inc.Inventors: Gregory M. Shutske, Brian S. Freed, John D. Tomer, IV, R. Richard L. Hamer
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Patent number: 5631405Abstract: 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.Type: GrantFiled: June 7, 1995Date of Patent: May 20, 1997Assignee: Pharm-Eco Laboratories, IncorporatedInventors: Biman Pal, Siya Ram, Bing Cai, Yesh P. Sachdeva, Jaechul Shim, Salah A. Zahr, Emile Al-Farhan, Richard L. Gabriel
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Patent number: 5618966Abstract: 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.Type: GrantFiled: May 16, 1995Date of Patent: April 8, 1997Assignee: Pharm-Eco Laboratories, IncorporatedInventors: Biman Pal, Siya Ram, Bing Cai, Yesh P. Sachdeva, Jaechul Shim, Salah A. Zahr, Emile Al-Farhan, Richard Gabriel
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Patent number: 5599994Abstract: 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.Type: GrantFiled: June 7, 1995Date of Patent: February 4, 1997Assignee: Pharm-Eco Laboratories, Inc.Inventors: Biman Pal, Siya Ram, Yesh P. Sachdeva, Jaechul Shim, Salah A. Zahr, Emile Al-Farhan, Richard L. Gabriel
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Patent number: 5554794Abstract: The invention includes a compound of formula I ##STR1## where R' is hydrogen, an alkyl, or aryl group; R"O is derived from R"OH which is a polyether mono-ol or hydrocarbyl mono-ol; and R"' independently is a hydrogen, an alkyl group or a substituted alkyl group. The invention also includes an unleaded fuel composition containing a compound of formula I and a process for making the compound of formula I.Type: GrantFiled: August 18, 1994Date of Patent: September 10, 1996Assignee: Shell Oil CompanyInventor: Thomas H. Johnson
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Patent number: 5550291Abstract: 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.Type: GrantFiled: May 4, 1995Date of Patent: August 27, 1996Assignee: Bio-Mega/Boehringer Ingelheim Research, Inc.Inventors: Pierre L. Beaulieu, Yvan Guindon, Dominik M. Wernic
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Patent number: 5491233Abstract: 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.Type: GrantFiled: July 12, 1994Date of Patent: February 13, 1996Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Richard D. Broene, Nancy E. Lee
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Patent number: 5489682Abstract: 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.Type: GrantFiled: February 10, 1994Date of Patent: February 6, 1996Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Nancy E. Lee
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Patent number: 5475138Abstract: 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.Type: GrantFiled: July 7, 1994Date of Patent: December 12, 1995Assignee: Pharm-Eco Laboratories IncorporatedInventors: Biman Pal, Siya Ram, Bing Cai, Yesh P. Sachdeva, Jaechul Shim, Salah A. Zahr, Emile Al-Farhan, Richard Gabriel
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Patent number: 5442118Abstract: 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.Type: GrantFiled: April 22, 1994Date of Patent: August 15, 1995Assignee: Sepracor, Inc.Inventors: Yun Gao, Yaping Hong, Charles M. Zepp
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Patent number: 5344990Abstract: 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.Type: GrantFiled: October 5, 1993Date of Patent: September 6, 1994Assignee: Abbott LaboratoriesInventors: William R. Baker, Stephen L. Condon
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Patent number: 5238959Abstract: The present invention provides 3-(4-substitutedphenoxy)-3-phenyl propanamines capable of inhibiting the uptake of serotonin. These compounds are useful for treating many pharmacological disorders, including depression and obesity. These compounds can also be used to reduce the desire to smoke and consume alcohol.Type: GrantFiled: April 20, 1992Date of Patent: August 24, 1993Assignee: Eli Lilly and CompanyInventors: David W. Robertson, David T. Wong
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Patent number: 5235103Abstract: 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.Type: GrantFiled: December 15, 1992Date of Patent: August 10, 1993Assignee: SanofiInventors: Robert Boigegrain, Roberto Cecchi, Sergio Boveri
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Patent number: 5198586Abstract: 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.Type: GrantFiled: October 25, 1990Date of Patent: March 30, 1993Assignee: SanofiInventors: Robert Boigegrain, Roberto Cecchi, Sergio Boveri
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Patent number: 5189219Abstract: 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.Type: GrantFiled: December 19, 1991Date of Patent: February 23, 1993Assignee: Duphar International Research B.V.Inventors: Johannes Brussee, Arne van der Gen, Cornelis G. Kruse
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Patent number: 5099067Abstract: The present invention relates to a method of converting .beta.-nitro compounds, specifically alcohols, into the corresponding hydroxy amines with retention of configuration by the use of ammonium formate.Type: GrantFiled: August 15, 1991Date of Patent: March 24, 1992Assignee: Northwestern UniversityInventors: Anthony G. M. Barrett, Christopher D. Spilling
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Patent number: 4952729Abstract: There is disclosed an improved process for preparing albuterol which comprises reacting a 5-(haloacetyl)-2-hydroxybenzaldehyde with 1,1-dimethylethanamine in an organic solvent and in an inert atmosphere to form 5-[[(1,1-dimethylethyl)amino]acetyl]-2-hydroxybenzaldehyde and reducing the carbonyl functions to the corresponding hydroxy groups to form albuterol.Type: GrantFiled: November 3, 1989Date of Patent: August 28, 1990Assignee: Schering-Plough Corp.Inventors: Esther Babad, Nicholas Carruthers, Martin Steinman
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Patent number: 4914126Type: GrantFiled: September 23, 1987Date of Patent: April 3, 1990Assignee: Fisons plcInventors: John Dixon, Francis Ince
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Patent number: 4603019Abstract: This invention relates to new N-(methoxyphenacyl)-amine derivatives selected from the group consisting of(i) the N-(methoxyphenacyl)-alkylamines of the general formula ##STR1## wherein A is OCH.sub.3, and R is C.sub.3 -C.sub.8 -alkyl or C.sub.3 -C.sub.8 -hydroxyalkyl; and,(ii) addition salts thereof.These new derivatives are useful as pharmaceuticals, in particular as peripheral vasodilating agents.Type: GrantFiled: November 23, 1984Date of Patent: July 29, 1986Assignee: Laboratoire L. LafonInventor: Louis Lafon
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Patent number: 4490392Abstract: A benzylalcohol derivative of the formula: ##STR1## wherein R is hydroxy, benzyloxy, halogen or alkoxy having one to four carbon atoms, and Ring A is monomethoxyphenyl, dimethoxyphenyl, trimethoxyphenyl or 3,4-methylenedioxyphenyl, or a pharmaceutically acceptable acid addition salt thereof is prepared by reducing a compound of the formula: ##STR2## wherein R' is benzyloxy, halogen or alkoxy having one to four carbon atoms, and Ring A is the same as defined above, to give a compound of the formula: ##STR3## wherein R' and Ring A are the same as defined above, and when R' is benzyloxy, if required, further subjecting the compound [I'] to catalytic hydrogenation to give a compound of the formula: ##STR4## wherein Ring A is the same as defined above. The benzylalcohol derivative [I] is useful as an anti-diabetic agent.Type: GrantFiled: July 27, 1978Date of Patent: December 25, 1984Assignee: Tanabe Seiyaku Co., Ltd.Inventors: Muneyoshi Ikezaki, Takeshi Kanno, Hajime Iwai, Masanori Inamasu
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Patent number: 4461914Abstract: A method for the preparation of 1-(4'-amino-3',5'-dichlorophenyl)-2-alkyl)or dialkyl)aminoethanols. The method involves preparation of the above compounds from the corresponding aminoketones by reduction with hydrogen in the presence of platinum oxide catalyst and a promoter, such as stannous chloride.Type: GrantFiled: February 1, 1983Date of Patent: July 24, 1984Assignee: American Cyanamid CompanyInventor: Terence J. Bentley
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Patent number: 4408074Abstract: A process for preparing 1-(3,5-dimethoxy-4-hydroxy phenyl)-2-(N-methylamino) ethanol hydrochloride is described by reacting 2,6-dimethoxyphenol with anhydrous chloral in the presence of a catalyst, hydrolyzing 1-(3,5-dimethoxy-4-hydroxyphenyl)2,2,2-trichloro ethanol and subsequently isolating the 3,5-dimethoxy-4-hydroxyphenyl glyoxal thus obtained; finally, this compound, in the form of the bisulfite, is directly converted to the desired product by amination with methylamine in the presence of hydrogen with a hydrogenation catalyst and the final product is converted into the hydrochloride.Type: GrantFiled: November 2, 1981Date of Patent: October 4, 1983Assignee: Dr. Lo. Zambeletti S.p.A.Inventors: Massimo Signorini, Attilio Trebbi, Luigi Molteni
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Patent number: RE35128Abstract: 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.Type: GrantFiled: June 7, 1994Date of Patent: December 19, 1995Assignee: Duphar International Research B.V.Inventors: Johannes Brussee, Arne van der Gen, Cornelis G. Kruse