Carbonyl Of Aldehyde Or Ketone Reacted To Form Oxirane Ring Patents (Class 549/519)
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Patent number: 11203580Abstract: The present invention refers to a process for reacting an alkyl aryl ketone obtaining thereby the corresponding aryl oxirane or ?-functionalized alkyl aryl ketal, the aryl oxirane or ?-functionalized alkyl aryl ketal obtained by the process as well as the ?-functionalized ketone obtained by the process.Type: GrantFiled: April 19, 2018Date of Patent: December 21, 2021Assignee: IGM GROUP B.V.Inventor: Reinhard Sommerlade
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Patent number: 8981127Abstract: The present invention relates to a process for the preparation of nebivolol and, more particularly, to an improved process of synthesizing an alpha-haloketone of formula a key intermediate in the preparation of nebivolol.Type: GrantFiled: September 22, 2009Date of Patent: March 17, 2015Assignee: Zach SystemInventors: Yvon Derrien, Eric Chenard, Alain Burgos
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Publication number: 20140316149Abstract: This disclosure is directed to methods of preparing organic aldehydes, each method comprising contacting a terminal olefin with an oxidizing mixture comprising: (a) a dichloro-palladium complex; (b) a copper complex; (c) a source of nitrite; under aerobic reaction conditions sufficient to convert at least a portion of the terminal olefin to an aldehyde.Type: ApplicationFiled: April 17, 2014Publication date: October 23, 2014Applicant: CALIFORNIA INSTITUTE OF TECHNOLOGYInventors: ZACHARY K. WICKENS, BILL MORANDI, ROBERT H. GRUBBS, KACPER SKAKUJ, SARAH BRONNER
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Publication number: 20130274488Abstract: A mixture of compounds containing 1,3-dichloropropan-2-ol, 2,3-dichloropropan-1-ol, and a halogenated ketone, where the halogenated ketone content of the mixture is at least 0.0001% by weight and less than or equal to 0.1% by weight relative to the 1,3-dichloropropan-2-ol and 2,3-dichloropropan-1-ol.Type: ApplicationFiled: June 7, 2013Publication date: October 17, 2013Inventor: Patrick GILBEAU
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Publication number: 20120289721Abstract: A process for the preparation of an 1,1-disubstituted oxirane is disclosed, wherein an organic sulphide is reacted in a polar solvent with an educt containing a leaving group attached to a primary or secondary carbon atom, and/or the sulfonium salt formed in this way is reacted with a ketone in presence of a base and a polar solvent. Oxiranes of the type obtained may be further converted into the corresponding ?-hydroxyketone or ?-aminoketone, either in one step by subjecting to aerobic oxidation in the presence of a transition metal catalyst, or in two steps by hydrolyzation in the presence of an aqueous acid to the corresponding dialcohol and subsequent selective oxidation. Further described are some novel epoxide intermediates. The ?-hydroxyketones and ?-aminoketones thus obtainable are useful inter alia as photoinitiators.Type: ApplicationFiled: July 25, 2012Publication date: November 15, 2012Inventors: NICOLE END, Reinhard H. Sommerlade, Yvonne Richter
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Publication number: 20120238762Abstract: To provide an azole derivative which is contained as an active ingredient in an agro-horticultural agent having an excellent controlling effect on diseases. An azole derivative according to the invention is represented by Formula (I), wherein R1 and R2 are same or different, and each denotes a substituted C3-C6 cycloalkyl group or a C1-C4 alkyl group substituted with the substituted C3-C6 cycloalkyl group; and A denotes a nitrogen atom or a methyne group.Type: ApplicationFiled: November 29, 2010Publication date: September 20, 2012Applicant: KUREHA CORPORATIONInventors: Keiichi Sudo, Takashi Shimokawara, Eiyu Imai, Nobuyuki Kusano, Hisashi Kanno, Taiji Miyake, Masaru Mori, Toshihide Saishoji
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Publication number: 20110178305Abstract: The present invention relates to a process for the preparation of threo-3,4-epoxy-2-amino-1-substituted butane derivatives represented by general Formula I which comprises reacting compound of Formula III or salt thereof with an active ester of acid of Formula IV and treating the product thereof with base. The carbon atom bonded to the radical R3 in Formula I and IV is in the (R)-, (S)- or (R,S)-configuration. The compounds of Formula I and III, particularly in their (2S,3R) configuration are useful intermediates for the preparation of atazanavir bisulfate.Type: ApplicationFiled: May 5, 2009Publication date: July 21, 2011Applicant: RANBAXY LABORATORIES LIMITEDInventors: Rakesh Singh, Prasad Yeragorla, Mahavir Singh Khanna, Mohan Prasad
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Publication number: 20110124891Abstract: Compounds of formula (I): are disclosed. In these compounds Y is —CH(OH)—, —CH(NHR6)—, —C(=0)-, —CH?CHCO— or—formula (II)—and R1 and R2 are hydrogen, OH, alkyl, alkoxy, benzyloxy and aryl, and, when Y is —CH(OH)—, additionally alkenyl or alkynyl. Processes for the production of these compounds are also disclosed.Type: ApplicationFiled: August 16, 2008Publication date: May 26, 2011Inventors: John Welch, Silvana Ngo, Dong Sung Lim
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Publication number: 20110009650Abstract: A process is claimed for the enantioselective epoxidation of ?,?-unsaturated ketones, in which a compound of the general formula I, is reacted with an oxidizing agent to form ?,?-epoxy ketones of the general formula II, in which R1, R2, R3 are as defined above. The ?,?-epoxy ketones of the general formula II can be obtained in good yields and outstanding enantioselectivities from ?,?-unsaturated ketones of the general formula I by epoxidation with hydrogen peroxide in the presence of a chiral catalyst, such as amino compounds and their acid addition salts.Type: ApplicationFiled: March 12, 2009Publication date: January 13, 2011Applicant: Studiengesellschaft Kohle MBHInventors: Benjamin List, Corinna Reisinger, Xingwang Wang
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Patent number: 7709553Abstract: The invention provides a cation polymerizable resin composition excellent in curing properties and corrosion resistance with less resin coloration and less cure shrinkage, which is a material suitable as a surface protective material for optical disk. Specifically, the cation polymerizable resin composition comprises an epoxy compound (A) as an essential ingredient represented by formula 1 wherein R1 and R2 each represent a saturated or unsaturated carbon atom, and R3 represents a hydrogen atom or a saturated or unsaturated carbon atom, a cation polymerizable compound (B) other than the epoxy compound represented by formula 1, a photo cation polymerization initiator (C) and a photo radical polymerization initiator (D).Type: GrantFiled: April 16, 2004Date of Patent: May 4, 2010Assignee: Mitsui Chemicals, Inc.Inventors: Yuichi Ito, Satoru Suda, Yasushi Mizuta, Katsunori Nishiura, Toshikazu Gomi
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Publication number: 20090287006Abstract: The invention relates to a process comprising a condensation step wherein a starting aldehyde or ketone is made to react with an ester of an ?-haloacid to form an epoxy compound, whereby the reaction is carried out in the presence of a dipolar aprotic compound selected from the group consisting of 1-methyl-2-pyrrolidone (NMP), hexamethylphosphorous triamide (HMPT), dimethylsulfoxide (DMSO), and urea derivatives of the following formula: (III) wherein R1, R2, R3 and R4 may each independently be H or a C1-C4 alkyl group and whereby R2 and R3 may together form a heterocyclic group.Type: ApplicationFiled: September 13, 2006Publication date: November 19, 2009Inventors: Jochen Stangl, Claude Stritt
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Publication number: 20090018354Abstract: A process for the preparation of an 1,1-disubstituted oxirane is disclosed, wherein an organic sulphide is reacted in a polar solvent with an educt containing a leaving group attached to a primary or secondary carbon atom, and/or the sulfonium salt formed in this way is reacted with a ketone in presence of a base and a polar solvent. Oxiranes of the type obtained may be further converted into the corresponding ?-hydroxyketone or ?-aminoketone, either in one step by subjecting to aerobic oxidation in the presence of a transition metal catalyst, or in two steps by hydrolyzation in the presence of an aqueous acid to the corresponding dialcohol and subsequent selective oxidation. Further described are some novel epoxide intermediates. The ?-hydroxyketones and ?-aminoketones thus obtainable are useful inter alga as photoinitiators.Type: ApplicationFiled: June 29, 2005Publication date: January 15, 2009Applicant: CIBA SPECIALTY CHEMICALS HOLDING INC.Inventors: Nicole End, Reinhard H. Sommerlade, Yvonne Richter
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Patent number: 7459573Abstract: An epoxy compound of the formula (1): wherein, R represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms, and Ar represents an optionally substituted aromatic group, can be purified by dissolving a crude product containing the epoxy compound (1), an aprotic polar solvent and an alkali metal salt in a two-phase solvent composed of water and an organic solvent, which is capable of phase-separating from water, obtaining the organic layer by phase separation, washing with water and then subjecting to isolation of the epoxy compound (1) without decomposition.Type: GrantFiled: August 14, 2007Date of Patent: December 2, 2008Assignee: Sumitomo Chemical Company, LimitedInventors: Tadashi Mizuno, Nobuhiro Arai, Erina Honda, Hideo Muraoka
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Publication number: 20080279800Abstract: A compound of formula (I): wherein each R independently represents H, methanol or ethanol, and Z represents O or S.Type: ApplicationFiled: February 28, 2008Publication date: November 13, 2008Applicant: Flexitral, Inc.Inventor: Luca TURIN
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Publication number: 20080249324Abstract: A process for preparing 1,3-dibromoacetone, 1-3-dichloroacetone and epichlorohydrin which comprises: (a) reacting acetone with 2 moles of bromine to make a mixture of brominated acetone derivatives and byproduct hydrogen bromide; (b) equilibrating the mixture of brominated acetone derivatives and hydrogen bromide to produce 1,3-dibromoacetone as the major product; (c) crystallizing the 1,3-dibromoacetone; and (d) isolating the 1,3-dibromoacetone. The process may further include the steps of (e) reacting the 1,3-dibromoacetone with a chloride source to produce 1,3-dichloroacetone; (f) hydrogenating the isolated 1,3-dichloroacetone to produce 1,3-dichlorohydrin; and (g) cyclizing the 1,3-dichlorohydrin with a base to produce epichlorohydrin.Type: ApplicationFiled: May 17, 2005Publication date: October 9, 2008Inventor: Clark S. Davis
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Patent number: 7361790Abstract: Epichlorohydrin is produced from acetone by (1) chlorinating acetone to form monochloroacetone; (2) disproportionating the monochloroacetone in the presence of a platinum catalyst, a strong acid and preferably a chloride source (for example, added as a salt or from hydrolysis of monochloroacetone) and some water to produce acetone and 1,3-dichloroacetone; (3) hydrogenating the 1,3-dichloroacetone in the presence of a catalyst to produce 1,3-dichlorohydrin; and (4) cyclizing the 1,3-dichlorohydrin with a base to produce epichlorohydrin.Type: GrantFiled: March 24, 2005Date of Patent: April 22, 2008Assignee: Dow Global Technologies Inc.Inventors: Marvin L. Dettloff, Marty J. Null
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Patent number: 7189864Abstract: A synthesis is described for intermediates which are readily amenable to the large scale preparation of hydroxyethylurea-based chiral HIV protease inhibitors. The method includes forming a diastereoselective epoxide from a chiral alpha amino aldehyde.Type: GrantFiled: October 13, 2004Date of Patent: March 13, 2007Assignee: G.D. Searle & Co.Inventors: John S. Ng, Claire A. Przybyla, Richard A. Mueller, Michael L. Vazquez, Daniel P. Getman
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Patent number: 6974876Abstract: A synthesis is described for intermediates which are readily amenable to the large scale preparation of hydroxyethylurea-based chiral HIV protease inhibitors. The method includes forming a diastereoselective epoxide from a chiral alpha amino aldehyde.Type: GrantFiled: February 10, 2003Date of Patent: December 13, 2005Assignee: G.D. Searle & Co.Inventors: John S Ng, Claire A. Przybyla, Richard A Mueller, Michael L Vazquez, Daniel P Getman
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Patent number: 6867311Abstract: The present invention provides compounds and methods that can be used to convert the intermediate halomethyl ketones (HMKs), e.g., chloromethyl ketones, to the corresponding S,S- and R,S-diastereomers. More particularly, the present invention provides: (1) reduction methods; (2) inversion methods; and (3) methods involving the epoxidation of alkenes. Using the various methods of the present invention, the R,S-epoxide and the intermediary compounds can be prepared reliably, in high yields and in high purity.Type: GrantFiled: April 14, 2003Date of Patent: March 15, 2005Assignee: Aerojet Fine Chemicals LLCInventors: Aslam A. Malik, Todd E. Clement, Hasan Palandoken, James Robinson, III, Joy A. Stringer
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Patent number: 6756502Abstract: Processes for the preparation of Venlafaxine (IX) via the novel epoxy-nitrile intermediate (I), which when subjected to hydrogenation forms compound (X), and may subsequently be reduced to yield the desired product (IX). The epoxy-nitrile intermediate (I) itself may be synthesized via various alternative reaction strategies, from a range of starting materials. E.g. 4-methoxy-benzaldehyde (VI), upon treatment with cyclohexyl magnesium bromide yields compound (V). This in turn may be oxidized to yield compound (III), which forms compound (II) on treatment with an (x-keto-halogenation agent. Cyanation of compound (II), then yields the desired epoxy nitrile intermediate (I), from which Venlafaxine (IX) may be synthesized.Type: GrantFiled: April 10, 2002Date of Patent: June 29, 2004Assignee: Alembic LimitedInventors: Dhiraj Mohansinh Rathod, Srinivasan Rengaraju, Milind Moreshwar Gharpure, Nishant Mahendra Patel, Mandar Manohar Deoahar
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Publication number: 20030236419Abstract: An epoxytriazole derivative (V) useful as an intermediate for anti-fungal agents and an intermediate therefor having high quality can be produced economically and efficiently by the following industrial means. A compound of the following formula (I) is reacted with trimethyloxosulfonium salt and the like in the presence of a base to give compound (II), this compound is converted to compound (IV), and this compound is reacted with 1,2,4-triazole in the presence of a base.Type: ApplicationFiled: December 31, 2002Publication date: December 25, 2003Applicant: Sumika Fine Chemicals Co., Ltd.Inventors: Weiqi Wang, Tetsuya Ikemoto
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Patent number: 6653419Abstract: A method for producing partially fluorinated epoxides and corresponding polyether homopolymers of these polyfluorinated epoxides is described. Also described is a method for incorporating a fluoroalcohol functional group into a polymer as a pendant group. Certain perfluorinated olefins are also described. These polyfluorinated epoxides and the associated polymers and methods relating to them are useful components in photoresists, particulary in lithographic photoresists for use at low ultraviolet wavelengths (e.g., 157 nm).Type: GrantFiled: October 3, 2001Date of Patent: November 25, 2003Assignee: E. .I du Pont de Nemours and CompanyInventors: Viacheslav Alexandrovich Petrov, Andrew Edward Fiering, Jerald Feldman
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Patent number: 6570027Abstract: A synthesis is described for intermediates which are readily amenable to the large scale preparation of hydroxyethylurea-based chiral HIV protease inhibitors. The method includes forming a diastereoselective epoxide from a chiral alpha amino aldehyde.Type: GrantFiled: April 3, 2002Date of Patent: May 27, 2003Assignee: G. D. Searle & Co.Inventors: John S Ng, Claire A. Przybyla, Richard A Mueller, Michael L Vazquez, Daniel P Getman
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Patent number: 6559323Abstract: A process for the preparation of an oxirane, aziridine or cyclopropane of formula (I), wherein X is oxygen, NR4 or CHR5; R1 is hydrogen, alkyl, aryl, heteroaromatic, heterocyclic or cycloalkyl; R2 is hydrogen, alkyl, aryl, heteroaromatic, CO2R8, CHR14NHR13, heterocyclic or cycloalkyl; or R1 and R2 join together to form a cycloalkyl ring; R3 and R10 are, independently, hydrogen, alkyl, aryl, heteroaromatic, CO2R8, R83Sn, CONR8R9, trialkylsilyl or triarylsilyl; R4 is an electron withdrawing group; R5 is alkyl, cycloalkyl, aryl, heteroaromatic, SO2R8, SO3R8, COR8, CO2R8, CONR8R9, PO(R8)2, PO(OR8)2 or CN; R8 and R9 are independently alkyl or aryl; and R13 and R14 are independently hydrogen, alkyl or aryl is provided. The process comprises degrading a compound of formula (II), (IIa), (IIb) or (IIc): wherein R3 and R10 are as defined above; Y is a cation; depending on the nature of Y, r is 1 or 2; and L is a suitable leaving group, to form a diazo compound.Type: GrantFiled: February 28, 2000Date of Patent: May 6, 2003Assignees: Avecia Limited, University of SheffieldInventors: John Richard Studley, Varinder Kumar Aggarwal
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Patent number: 6500971Abstract: An ester compound of formula (1) is provided. R1 is H or methyl, R2 is tertiary C4-20 alkyl, and k=0 or 1. A resist composition comprising as the base resin a polymer resulting from the ester compound is sensitive to high-energy radiation, has excellent sensitivity, resolution, etching resistance and substrate adhesion, and is suited for micropatterning using electron beams or deep-UV.Type: GrantFiled: June 5, 2001Date of Patent: December 31, 2002Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takeru Watanabe, Takeshi Kinsho, Koji Hasegawa, Tsunehiro Nishi, Mutsuo Nakashima, Seiichiro Tachibana, Jun Hatakeyama
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Patent number: 6399793Abstract: The present invention relates to a process for the preparation of &agr;′ chloroketones, such as 4-phenyl-3-t-butyloxy-carbonylamino)-2-keto-1-chlorobutane by reacting certain aryl amino acid esters, e.g. N-(2-t-butoxycarbonyl)-L-phenylalanine-4-nitrophenyl ester, with a sulfur ylide compound to form the corresponding keto ylide compound which is then treated with a source of chloride and an organic acid.Type: GrantFiled: July 18, 2001Date of Patent: June 4, 2002Assignee: Bristol-Myers Squibb CompanyInventors: David Kronenthal, Mark D. Schwinden
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Patent number: 6388094Abstract: A synthesis is described for intermediates which are readily amenable to the large scale preparation of hydroxyethylurea-based chiral HIV protease inhibitors. The method includes forming a diastereoselective epoxide from a chiral alpha amino aldehyde.Type: GrantFiled: November 1, 1999Date of Patent: May 14, 2002Assignee: G.D. Searle & Co.Inventors: John S Ng, Claire A. Przybyla, Richard A Mueller, Michael L Vazquez, Daniel P Getman
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Patent number: 6316641Abstract: The invention concerns a method for preparing an epoxide, in particular glycidol, wherein a cyclic organic carbonate, in particular glycerol carbonate, is heated under reduced pressure so as to carry out a reaction to contract the carbonate ring into an epoxide ring. According to the present invention, the reaction is carried out in a solid/liquid system in the presence of a polyol and a solid catalyst consisting of a type A zeolite or &ggr;-alumina. The method, which may be carried out continuously, enables the epoxide to be formed in a single step, the epoxide being exhausted in the form of vapor which only has to be extracted and separated from the carbon dioxide formed.Type: GrantFiled: September 8, 1999Date of Patent: November 13, 2001Assignee: Organisation Nationale Interprofessionelle des Oleagineux (O.N.I.D.OL.)Inventors: Jeong-Woo Yoo, Zéphirin Mouloungui, Antoine Gaset
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Patent number: 6232478Abstract: The present invention relates to a process for the preparation of chiral 3,4-epoxybutyric acid expressed by formula (1) and the salt thereof, wherein (S)-3-activated-hydroxybutyrolactone expressed by formula (2) is subjected to a ring-opening reaction to obtain 4-hydroxy-3-activated hydroxybutyric acid expressed by formula (3), which is subjected to an epoxydation with an inversion of the chiral center.Type: GrantFiled: January 14, 2000Date of Patent: May 15, 2001Inventors: Il Suk Byun, Kyung Il Kim, Yoon Hwan Choi
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Patent number: 6211388Abstract: A method for producing propylene oxide by reacting propylene with ethylbenzene hydroperoxide, wherein the reaction is conducted in the presence of a catalyst comprising a titanium-containing silicon oxide and satisfying all of the following conditions (1) to (6): (1) there is at least one peak showing a interplanar spacing (d) larger than 18 Å in X-ray diffraction; (2) an average pore size is 10 Å or more; (3) a pore size of 90% or more of the total pore volume is 5 to 200 Å; (4) a specific pore volume is 0.2 cm3/g or more; (5) a quaternary ammonium ion represented by the following general formula (I) is used as a template and then said template is removed by calcination operation: [NR1R2R3R4]+ (I) wherein R1 represents a linear or branched hydrocarbon chain having 2 to 36 carbon atoms, and R2 to R4 represent an alkyl group having 1 to 6 carbon atoms; and (6) The catalyst has been subjected to silylation treatment.Type: GrantFiled: October 8, 1999Date of Patent: April 3, 2001Assignee: Sumitomo Chemical Company, LimitedInventors: Junpei Tsuji, Jun Yamamoto, Avelino Corma Canos, Fernando Rey Garcia
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Patent number: 6143909Abstract: Cryptophycin compounds possessing a .beta.-epoxy moiety may be made with high stereoselectivity at various steps in the overall synthetic process. This invention also provides novel intermediates useful in preparing Cryptophycin compounds.Type: GrantFiled: August 24, 1999Date of Patent: November 7, 2000Assignee: Eli Lilly and CompanyInventors: David Warren Hoard, Eric David Moher, Vinod Francis Patel, Bryan Hurst Norman
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Patent number: 6127556Abstract: In a method of preparing an aminoepoxide wherein a protected aminoaldehyde is reacted with a halomethyl organometallic reagent in an appropriate solvent at a temperature above -80.degree. C., wherein said halomethyl organometallic reagent is formed by reaction between an organometallic reagent and a dihalomethane, the improvement comprising flowing said protected aminoaldehyde into a mixing zone maintained at a temperature below 0.degree. C., also flowing said halomethyl organometallic reagent in said mixing zone for contacting in said mixing zone with said protected aminoaldehyde and also withdrawing from said mixing zone reaction products of said protected aminoaldehyde and said halomethyl organometallic reagent.Type: GrantFiled: December 16, 1997Date of Patent: October 3, 2000Assignee: G. D. Searle & Co.Inventors: Chin Liu, John S. Ng, James R. Behling, Arthur L. Campbell
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Patent number: 6121468Abstract: A process for producing amide derivatives represented by general formula (XV) ##STR1## or enantiomers thereof, novel intermediate compounds useful for producing these compounds, etc., and a process for producing the same, wherein each symbol is as defined in the specification. Compared with the conventional processes, the above process can be very easily effected and enables an efficient production of the compounds (XV), i.e., those involving the compounds (XVI) having an HIV protease inhibitory effect in high yields. The novel intermediates are highly advantageous as intermediates for producing not only the above compounds (XVI) but also those which are useful as an X-ray contrast medium, etc.Type: GrantFiled: May 19, 1998Date of Patent: September 19, 2000Assignees: Japan Tobacco Inc., Agouron Pharmaceuticals, Inc.Inventors: Takashi Inaba, Yasuki Yamada, James Shanley, Michael Deason
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Patent number: 6025506Abstract: The invention relates to a process for preparing an optically active trans-compound having formula (1), in which R represents a phenyl group, whether or not substituted, preferably p-methoxyphenyl, and A is derived from an optically active compound, in which an aldehyde having formula (2), in which R is as defined above, is, in the presence of a base, brought into contact with an optically active acetyl compound having formula (3), in which X represents a leaving group and in which A is derived from an amino alcohol, preferably a .beta.-amino alcohol having a rigid structure.Particularly good results were obtained when use was made of a compound having formula (3), in which A is derived from an amino indanol compound having formula (4), in which R.sub.1 and R.sub.2 represent a (hetero)alkyl or (hetero)aryl group, whether or not substituted, having 1-10 C atoms, or R.sub.1 and R.sub.2 constitute an aromatic or aliphatic ring together with the N atom to which they are bound, in particular in which R.sub.Type: GrantFiled: February 23, 1998Date of Patent: February 15, 2000Assignee: DSM N.V.Inventors: Bernardus Kaptein, Gerardus K. M. Verzijl
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Patent number: 5998637Abstract: A process for preparing an optically active trans-3-substituted glycidic acid ester compound of the formula (I): ##STR1## wherein ring A is a substituted or unsubstituted benzene ring, and R.sup.1 is an ester residue, which comprises:preparing a solution of one optical isomer (A) and the other optical isomer (B) of the ester compound (I), both of which are the optical isomers due to the asymmetric carbons at 2- and 3-positions, and an ester compound (B') which is different from the isomer (B) only in the ester residue R.sup.Type: GrantFiled: February 27, 1998Date of Patent: December 7, 1999Assignee: Tanabe Seiyaku Co., Ltd.Inventors: Masakatsu Furui, Toshiyuki Furutani
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Patent number: 5919956Abstract: A process for the manufacture of an optionally protected 4,8,8-trimethyl-1-oxaspiro?2.5!oct-4-en-6-ol (I) starting from protected 4-hydroxy-2,6,6-trimethyl-2-cyclohexen-1-one (II) comprises reacting the protected compound (II) with dihalomethyllithium and, if desired, cleaving off the protecting group from the thus-obtained protected 4,8,8-trimethyl-1-oxaspiro?2.5!oct-4-en-6-ol. The dihalomethyllithium can be produced in situ by reacting a dihalomethane with a lower alkyllithium in the presence of the compound of formula II. Preferably, protected (S)-4-hydroxy-2,6,6-trimethyl-2-cyclohexen-1-one is converted into protected (3S,6S)-4,8,8-trimethyl-1-oxaspiro?2.5!oct-4-en-6-ol in this manner. Both the starting material (II) and the end product (I) of the process in accordance with the invention are known, valuable intermediates for the manufacture of carotenoids.Type: GrantFiled: September 29, 1997Date of Patent: July 6, 1999Assignee: Roche Vitamins Inc.Inventors: Hans Hilpert, Erich Widmer
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Patent number: 5750740Abstract: A process for transforming a carbonyl compound into its corresponding epoxide, which comprises contacting the carbonyl compound with either trimethylsulphonium hydrogen sulphate and/or bis(trimethylsulphonium) sulphate or trimethylsulphoxonium hydrogen sulphate and/or bis(trimethylsulphoxonium) sulphate, in the presence of a base.Type: GrantFiled: May 25, 1995Date of Patent: May 12, 1998Assignee: Zeneca LimitedInventors: Raymond Vincent Heavon Jones, Elizabeth Shearer Currie Simpson
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Patent number: 5703246Abstract: A process for the preparation of an oxirane, aziridine or cyclopropane of formula (I) wherein, X is oxygen, NR.sup.4 or CHR.sup.5 ; R.sup.1 is hydrogen, alkyl, aryl, heteroaromatic, heterocyclic or cycloalkyl; R.sup.2 is hydrogen, alkyl, aryl, heteroaromatic, CO.sub.2 R.sup.8, CHR.sup.14 NHR.sup.13, heterocyclic or cycloalkyl; or R.sup.1 and R.sup.2 join together to form a cycloalkyl ring; R.sup.3 is hydrogen, alkyl, aryl, heteroaromatic, CO.sub.2 R.sup.8, R.sup.8.sub.3 Sn, CONR.sup.8 R.sup.9 or trimethylsilyl; R.sup.4 and R.sup.5 are, independently, alkyl, cycloalkyl, aryl, heteroaromatic, SO.sub.2 R.sup.8, SO.sub.3 R.sup.8, COR.sup.8, CO.sub.2 R.sup.8, CONR.sup.8 R.sup.9 or CN, or R.sup.4 can also be P(O)(aryl).sub.2 ; R.sup.8 and R.sup.9 are independently alkyl, aryl or arylalkyl; R.sup.13 and R.sup.14 are independently hydrogen, alkyl or aryl; the process comprising reacting a mixture of a compound of formula (II), wherein R.sup.1, R.sup.2 and X are as defined above, and a sulphide of formula SR.sup.6 R.Type: GrantFiled: March 15, 1996Date of Patent: December 30, 1997Assignee: Zeneca LimitedInventors: Varinder Kumar Aggarwal, Hesham Nimer Hasan Abdel-Rahman, Hee Yoon Lee
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Patent number: 5637727Abstract: A process for transforming a carbonyl compound into its corresponding epoxide, which comprises contacting the carbonyl compound with either trimethylsulphonium hydrogen sulphate and/or bis(trimethylsulphonium) sulphate or trimethylsulphoxonium hydrogen sulphate and/or bis(trimethylsulphoxonium) sulphate, in the presence of a base.Type: GrantFiled: August 10, 1993Date of Patent: June 10, 1997Assignee: Zeneca LimitedInventors: Raymond V. H. Jones, Elizabeth S. C. Simpson
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Patent number: 5606006Abstract: Cure of a novel trisepoxy resin-based composition provides a thermoset having high Tg, low dielectric constant, low water absorption and good flexural strength.Type: GrantFiled: April 8, 1996Date of Patent: February 25, 1997Assignee: Shell Oil CompanyInventor: Pen-Chung Wang
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Patent number: 5583238Abstract: A synthesis is described for intermediates which are readily amenable to the large scale preparation of hydroxyethylurea-based chiral HIV protease inhibitors. The method includes forming a diastereoselective epoxide from a chiral alpha amino aldehyde.Type: GrantFiled: December 16, 1994Date of Patent: December 10, 1996Assignee: G. D. Searle & Co.Inventors: John S. Ng, Claire A. Przybyla, Richard A. Mueller, Michael L. Vazquez, Daniel P. Getman
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Patent number: 5408033Abstract: An epoxide is produced by reacting a sulfonium salt with a ketone in the presence of a low molecular weight alcohol or ether and an alkali metal hydroxide at a temperature of from about 60.degree. to about 90.degree. C. The alkali metal hydroxide is in the solid form. The reaction is generally carried out in the presence of an organic solvent such as toluene. The preferred low molecular weight ether is diethylene glycol. Water is not added to the reaction mixture.Type: GrantFiled: April 1, 1993Date of Patent: April 18, 1995Assignee: Miles Inc.Inventor: Dennis E. Jackman
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Patent number: 5256802Abstract: Oxiranes are made from ketones by heating a ketone which is preferably an alkyl ketone to a temperature of from about 60.degree. to about 90.degree. C. (preferably about 80.degree. C.) in the presence of a sulfonium salt, a quaternary ammonium salt and a potassium hydroxide solution which is at least 61% potassium hydroxide. It is preferred that no organic solvent be included in the reaction mixture. The potassium hydroxide is generally included in an amount such that for every mole of ketone, from about 3 to about 4 moles of potassium hydroxide are present. The sulfonium salt is generally used in an amount of at least 1.1 moles for each mole of ketone. The quaternary ammonium salt is generally used in an amount of from about 1 to about 5 mol % based on moles of ketone present.Type: GrantFiled: April 3, 1990Date of Patent: October 26, 1993Assignee: Miles Inc.Inventors: Jeffrey D. Macke, Peter E. Newallis, Karl G. Steinbeck
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Patent number: 5194636Abstract: In the preparation of benzyl ketones of the formula ##STR1## a benzyl chloride of the formula ##STR2## is reacted with an acid chloride of the formulaR.sup.6 --CO--Cl (III)a) in a first stage with an excess of zinc powder in the presence of a diluent at a temperature between 80.degree. C. and 200.degree. C. under an inert gas atmosphere, and separating off the excess zinc powder, thereby to obtain a benzyl derivative of the formula ##STR3## and b) in a second stage reacting the benzyl derivative of the formula (IV) with an acid chloride of the formula (III) in the presence of a palladium catalyst and in the presence of a diluent at a temperature between 0.degree. C. and 150.degree. C. under an inert gas atmosphere.Type: GrantFiled: March 3, 1992Date of Patent: March 16, 1993Assignee: Bayer AktiengesellschaftInventors: Thomas Himmler, Udo Kraatz, Wolfgang Kramer, Klaus Stroech
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Patent number: 5159089Abstract: A process for selective production of a threo-epoxy compound of the formula: ##STR1## wherein Ar is a substituted or unsubstituted phenyl group and R.sup.1 and R.sup.2 are each a lower alkyl group, which comprises reacting a ketone compound of the formula: ##STR2## wherein Ar, R.sup.1 and R.sup.2 are each as defined above with a sulfur methylide of the formula: ##STR3## wherein A is a lower alkyl group or a substituted or unsubstituted phenyl group and B is a lower alkyl group, a substituted or unsubstituted phenyl group or a di(lower)-alkylamino group in an aqueous organic solvent.Type: GrantFiled: August 24, 1990Date of Patent: October 27, 1992Assignee: Sumitomo Pharmaceuticals Company, LimitedInventors: Naohito Ohashi, Koji Fujimoto, Yoshihiro Tanaka
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Patent number: 5146001Abstract: In the preparation of benzyl ketones of the formula ##STR1## a benzyl chloride of the formula ##STR2## is reacted with an acid chloride of the formulaR.sup.6 --CO--Cl (III)a) in a first stage with an excess of zinc powder in the presence of a diluent at a temperature between 80.degree. C. and 200.degree. C. under an inert gas atmosphere, and separating off the excess zinc powder, thereby to obtain a benzyl derivative of the formula ##STR3## and b) in a second stage reacting the benzyl derivative of the formual (IV) with an acid chloride of the formula (III) in the presence of a palladium catalyst and in the presence of a diluent at a temperature between 0.degree. C. and 150.degree. C. under an inert gas atmosphere.Type: GrantFiled: June 3, 1991Date of Patent: September 8, 1992Assignee: Bayer AktiengesellschaftInventors: Thomas Himmler, Udo Kraatz, Wolfgang Kramer, Klaus Stroech
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Patent number: 5099040Abstract: A new process for the preparation of 1-chloro-2-(1-chloro-cyclopropyl)-3-(2-chloro-phenyl)-propan-2-ol of the formula ##STR1## and/or 2-(1-chloro-cyclopropyl)-2-(2-chloro-benzyl)-oxirane of the formula ##STR2## comprising a) reacting in a first step, 2-chloro-benzyl chloride of the formula ##STR3## with comminuted magnesium in the presence of a mixture of toluene and tetrahydrofuran, in which the ratio of toluene to tetrahydrofuran is between 65:35 and 95:5 parts by weight, at a temperature between 0.degree. C. and 100.degree. C.Type: GrantFiled: August 23, 1991Date of Patent: March 24, 1992Assignee: Bayer AktiengesellschaftInventors: Winfried Rosen, Paul-Christian Fiedler, Gotz Blume
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Patent number: 5057624Abstract: New process for the synthesis of the N-methyl-3,4-dimetoxyphenylethylamine of formula ##STR1## intermediate in the synthesis of the drug internationally known as verapamil. The process starts from the 3,4-dimethoxybenzaldehyde which, by means of a Darzens condensation, gives an epoxyester that, by alkaline hydrolysis and subsequent decarboxylation, gives the 3,4-dimethoxyphenylacetaldehyde. This aldehyde gives the amine of formula I by reaction with monomethylamine followed by reduction with sodium borohydride.Type: GrantFiled: March 30, 1990Date of Patent: October 15, 1991Assignee: ALFA Wassermann S.p.A.Inventors: Vincenzo Cannata, Giancarlo Tamerlani, Graziano Zagnoni
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Patent number: 5008411Abstract: A process for the preparing a compound of the formula ##STR1## wherein R.sub.1 and R.sub.2 are each independently hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, trifluoromethyl or nitro; or R.sub.1 and R.sub.2 taken together with the benzene ring to which they are attached are naphthalene, and Ar is p-lower alkoxy phenyl.which comprises reacting ##STR2## wherein R.sub.1 and R.sub.2 are as described above with the compound of the formula ##STR3## wherein Ar is as described above, in an aromatic organic compound. The intermediates formed by the process of the invention are useful in the production of thiazepin-4(5H)-ones which have activity as calcium channel blockers and accordingly are useful as agents for lowering blood pressure and agents for treating ischemia.Type: GrantFiled: October 2, 1989Date of Patent: April 16, 1991Assignee: Hoffmann-La Roche Inc.Inventors: David L. Coffen, Pradeep B. Madan, Alan Schwartz
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Patent number: 4992565Abstract: A process for the preparation of an oxirane of the formula ##STR1## in which Y is chlorine or phenyl,X is oxygen or CH.sub.2, andZ is hydrogen or halogen, comprising reacting dimethyl sulphide with methyl bromide in the presence of an inert organic diluent thereby to produce trimethylsulphonium bromide of the formula(CH.sub.3).sub.3 S.sup..sym. Br.sup..crclbar.and reacting the trimethylsulphonium bromide with a ketone of the formula ##STR2## in the presence of a base and in the presence of an inert organic diluent, at a temperature between about 0.degree. C. and 60.degree. C. The end products are produced in high yield and are known intermediates for known fungicides.Type: GrantFiled: April 12, 1990Date of Patent: February 12, 1991Assignee: Bayer AktiengesellschaftInventors: Karl H. Mohrmann, Wolf Reiser, Siegfried W. Linke, Rudolf Zerbes