Plural Ring Oxygens In The Bicyclo Ring System Patents (Class 549/464)
-
Patent number: 6392062Abstract: The conversion rate of a homogeneously catalyzed reaction in which an educt is converted into a reaction product with addition or cleavage of a reaction partner or under isomerization in a liquid phase that contains an effective amount in dissolved form of a catalyst suitable for the reaction can be significantly increased in that the liquid phase containing the educt and homogeneous catalyst and, to the extent required, reaction partners [2nd] to be attached are brought into contact with a stationary or moved bed consisting of porous particles, especially particles with a pore volume of 0.1 to 3 ml/g. The liquid phase is preferably conducted in a trickle bed operation over a stationary fixed bed.Type: GrantFiled: November 14, 2000Date of Patent: May 21, 2002Assignee: Degussa AGInventor: Thomas Haas
-
Publication number: 20020032339Abstract: The invention provides a process for covalently coupling organic compounds which comprises reacting an aromatic ring compound having a halogen or halogen-like substituent at a coupling position with a diboron derivative in the presence of a Group VIII metal catalyst and a suitabIe base. The invention also provides useful arylboron intermediates.Type: ApplicationFiled: December 18, 1998Publication date: March 14, 2002Inventors: SEBASTIAN MARIO MARCUCCIO, MARY RODOPOULOS, HELMUT WEINGOLD
-
Publication number: 20020013482Abstract: The invention relates to a process for the preparation of dianhydrohexitol bis(4-acryloyloxy)acylate of the general formula 2 1Type: ApplicationFiled: June 26, 2001Publication date: January 31, 2002Applicant: Consortium fur elektrochemische Industrie GmbHInventors: Leonhard Brader, Norman Haberle, Markus Kriegbaum
-
Publication number: 20020013483Abstract: The invention relates to a process for the preparation of dianhydrohexitol bisacylates of the general formula (2), 1Type: ApplicationFiled: June 27, 2001Publication date: January 31, 2002Applicant: Consortium fur elektrochemische Industrie GmbHInventors: Leonhard Brader, Norman Haberle
-
Publication number: 20010051735Abstract: Novel derivatives of isosorbide mononitrate and its pharmaceutically acceptable salts, which have vasodilating activity with a reduced effect of tolerance, of the general formula (I) 1Type: ApplicationFiled: April 6, 2001Publication date: December 13, 2001Applicant: LACER, S.A.Inventors: Jose Repolles Moliner, Francisco Pubill Coy, Lydia Cabeza Llorente, Marcel.li Carbo Banus, Cristina Negrie Rofes, Juan Antonio Cerda Riudavets, Alicia Ferrer Siso, Marek W. Radomski, Eduardo Perez-Rasilla, Juan Martinez Bonnin
-
Patent number: 6316066Abstract: The invention relates to a thermochromic polymerizable mesogenic composition essentially consisting of: a) a component MA comprising at least one achiral polymerizable mesogenic compound comprising at least one polymerizable functional group, b) a component MB comprising at least one chiral polymerizable mesogenic compound comprising at least one polymerizable functional group, c) a photoinitiator, and d) optionally a dye component, to anisotropic polymers and polymer films with a chiral mesophase obtainable from said thermochromic polymerizable mesogenic composition and to the use of said thermochromic polymerizable mesogenic composition, anisotropic polymers and polymer films for optical information storage, photomasks, decorative pigments, cosmetics, security applications, active and passive optical elements such as polarizers or optical retarders, color filters, scattering displays, adhesives or synthetic resins with anisotropic mechanical properties.Type: GrantFiled: March 10, 2000Date of Patent: November 13, 2001Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Emma Jolliffe, David Coates
-
Patent number: 6313326Abstract: The invention relates to compounds with the general formula Y1—A1—M1—A2—Y2 wherein Y1 and Y2 are different from each other and Y1 is an acrylate or methacrylate residue and Y2 is a vinyl ether, epoxy, or azide residue, A1 and A2 are identical or different residues with the general formula CnH2n in which n is a whole number from 0 to 20 and one or more methylene groups can be replaced by oxygen atoms, and M1 has the general formula —R1—X1—R2—X2—R3—X3—R4— wherein R1, R2, R3, and R4 are identical or different doubly bonded residues from the group —O—, —COO—, —CONH—, —CO—, —S—, —C≡C—, —CH═CH—, —CH═N—, —CH2—, —N═N—, and —N═N(O)—, and R2—X2—R3 can also be a C—C bond, and X1, X2, and X3 are identical or different residues from the group 1,4-phenylene, 1,4-cyclohexylenType: GrantFiled: March 16, 2000Date of Patent: November 6, 2001Assignee: DaimlerChrysler AGInventors: Peter Strohriegl, Katja Strelzyk, Andreas Stohr, Petra Grundig, Michael Gailberger, Fritz Dannenhauer, Anne Barth
-
Publication number: 20010027211Abstract: The invention provides compounds, compositions and methods relating to novel arylsulfonanilide derivatives and their use as pharmacologically active agents. The compositions find particular use as pharmacological agents in the treatment of disease states, particularly cancer, psoriasis, vascular restenosis, infections, atherosclerosis and hypercholesterolemia, or as lead compounds for the development of such agents.Type: ApplicationFiled: February 21, 2001Publication date: October 4, 2001Applicant: Tularik Inc.Inventor: Jonathan B. Houze
-
Patent number: 6015899Abstract: Products are described which can be obtained by reacting components a), b) and c), where component a) is a compound of the formula I or a mixture of compounds of the formula I, component b) is a compound of the formula II or a mixture of compounds of the formula II and component c) is a compound of the formula III or a mixture of compounds of the formula III, ##STR1## in which the general symbols are as defined in claim 1, the compound of the formula I being, for example, pentaerythritol, thiodiethylene glycol, 1,4-butanediol, 1,4-propanediol, diethylene glycol, triethylene glycol, diethanolamine or glycerol, the compound of the formula II being, for example, sunflower oil or coconut fat, and the compound of the formula III being, for example, methyl 3-(3',5'-di-tert-butyl-4'-hydroxyphenyl)propionate. The abovementioned products can be used as liquid antioxidants in polymers and lubricants.Type: GrantFiled: April 21, 1997Date of Patent: January 18, 2000Assignee: Ciba Specialty Chemicals CorporationInventors: Paul Dubs, Roger Martin, Samuel Evans
-
Patent number: 5811313Abstract: A method for confirming the presence of highly refined sesame oil in pharmaceuticals. By extracting, concentrating and detecting sesamin and epi-sesamin, through the method disclosed in the present invention, highly refined sesame oil can be identified. The disclosed method can be performed at room temperature and does not require over night extraction. In practice, the disclosed method entails extracting sesamin from a sample with an organic solvent, transferring and evaporating the solvent layer to dryness to form a residue. An alkyl halide is added to the residue to form a mixture. The mixture and an organic solvent are passed through a separating means, generating an eluent, the eluent is then evaporated to dryness to form a second residue. A 1:1 solution of an organic solvent and an alkyl halide is added to the second residue in a volume sufficient to form a concentrated extract. The concentrated extract is then analyzed with high performance liquid chromatography.Type: GrantFiled: June 17, 1997Date of Patent: September 22, 1998Assignee: King Pharmaceuticals, Inc.Inventor: Mark Barr
-
Patent number: 5808056Abstract: The present invention relates to the process for the preparation of the substituted azetidinone having the formula: ##STR1## comprising a convergent synthesis wherein the azetidinone portion of the molecule is coupled to the lower benzodioxole portion via a base catalyzed addition to an isocyanate.Type: GrantFiled: October 23, 1996Date of Patent: September 15, 1998Assignee: Merck & Co., Inc.Inventors: Joseph S. Amato, Raymond Cvetovich, Frederick W. Hartner
-
Patent number: 5780629Abstract: The invention relates to chiral compounds containing at least one divalent or polyvalent chiral group, at least one polymerizable group, at least one spacer and at least one mesogenic group, and to their use as polymerizable, chiral dopes for the preparation of cholesteric networks. The novel compounds are suitable for use in electro-optical displays or as chiral dopes for nematic or cholesteric liquid crystals in order to produce layers which reflect in colors.Type: GrantFiled: June 6, 1996Date of Patent: July 14, 1998Assignee: BASF AktiengesellschaftInventors: Karl-Heinz Etzbach, Paul Delavier, Karl Siemensmeyer, Gerhard Wagenblast, Lothar Laupichler, Volkmar Vill
-
Patent number: 5744057Abstract: A polymerizable, chiral compound of the formula (I):(Z--Y.sup.1 -A-O--CO--O-M-Y.sup.2).sub.n X (I)where:A, M, Y.sup.1 and Y.sup.2, X, n and Z are as defined herein; and which compound is suitable for use in electro-optical displays or as chiral dopes for nematic or cholesteric liquid crystals for the production of layers which reflect in colors.Type: GrantFiled: June 5, 1996Date of Patent: April 28, 1998Assignee: BASF AktiengesellshaftInventors: Frank Meyer, Karl Siemensmeyer, Karl-Heinz Etzbach, Peter Schuhmacher
-
Patent number: 5731445Abstract: A 1,2-dioxetane derivative of formula (I): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.5 are each independently a hydrogen atom, an alkyl group, or an aryl group, R.sup.2 and R.sup.3 together and R.sup.4 and R.sup.5 together can be joined as a cyclo-alkyl group, R.sup.6 is a hydroxyl group, an alkoxyl group, an aralkyloxy group, --OSi(R.sup.8 R.sup.9 R.sup.10) in which R.sup.8, R.sup.9 and R.sup.10 are each independently an alkyl group, or a phosphate salt, and R.sup.7 is a hydrogen atom, a halogen atom, an alkyl group, or an alkoxyl group.Type: GrantFiled: December 2, 1996Date of Patent: March 24, 1998Assignee: Fujirebio Inc.Inventors: Masakatsu Matsumoto, Nobuko Watanabe, Hisako Kobayashi, Hiroshi Ikawa
-
Patent number: 5718845Abstract: Nonlinear optical compounds which contain a heteroaromatic ring and may further comprise a tricyanovinyl group attached to the heteroaromatic ring.Type: GrantFiled: January 18, 1995Date of Patent: February 17, 1998Assignee: Enichem S.p.A.Inventors: Kevin J. Drost, Pushkara Rao Varanasi, Kwan-Yue Alex Jen, Michael Anthony Drzewinski
-
Patent number: 5674894Abstract: The current invention discloses novel amidine derivatives with nitric oxide donating property that can inhibit platelet aggregation and promote vasodilation in a single compound.Type: GrantFiled: May 15, 1995Date of Patent: October 7, 1997Assignee: G.D. Searle & Co.Inventors: Mark G. Currie, Foe S. Tjoeng, Mark E. Zupec
-
Patent number: 5665766Abstract: A pharmaceutical product for the relief of the symptoms of angina pectoris and the like comprises an ester of an organic nitrate and a salicylate or derivative thereof having anti-platelet activity.Type: GrantFiled: January 30, 1995Date of Patent: September 9, 1997Assignee: Cal International LimitedInventors: William Byrne, Andrew Rynne
-
Patent number: 5614643Abstract: Process for the enzymatic production of isomerically pure compounds having the general formulae I and II ##STR1## in which the substituents R have the meanings stated in the claims, as well as their use for the production of isomerically pure isosorbide-2-nitrate having the formula V and isosorbide-5-nitrate having the formula VI, ##STR2## which are both important as therapeutic agents for coronary diseases.Type: GrantFiled: June 7, 1995Date of Patent: March 25, 1997Assignee: Boehringer Mannheim GmbHInventors: Manfred Schneider, Robert Seemayer
-
Patent number: 5011950Abstract: Novel aromatic amine derivatives of specific structure are useful intermediates for herbicides. The aromatic amine compounds have the structure shown by formula [I]: ##STR1## wherein Ar and A are as defined herein.Type: GrantFiled: February 2, 1988Date of Patent: April 30, 1991Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Daisuke Fukuoka, Katsuya Takahashi, Isao Hashimoto
-
Patent number: 4956384Abstract: Isosorbide 2- and 5-mononitrate esters with aliphatic, aryl, or cynnamic acids or diacids, or with alkylcarbonyloxy substituents optionally containing an isosorbide 2- or 5-mononitrate group, are useful in human therapy.Type: GrantFiled: May 4, 1988Date of Patent: September 11, 1990Assignee: Chiesi Farmaceutici S.p.A.Inventors: Paolo Chiesi, Vittorino Servadio
-
Patent number: 4883796Abstract: Oxime ethers of 2,6-dioxabicyclo[3.3.0]octanones of the formula I ##STR1## have pharmacological activity and are especially applicable as drugs for the prophylaxis and therapy of cardiac and circulatory diseases.Type: GrantFiled: February 2, 1988Date of Patent: November 28, 1989Assignee: Heinrich Mack Nachf.Inventors: Matyas Leitold, Peter Stoss
-
Patent number: 4863949Abstract: The present invention provides compounds of the general formula: ##STR1## wherein Ar is a substituted or unsubstituted aromatic or heteroaromatic radical, A is a straight-chained or branched alkylene chain containing up to 8 carbon atoms, a --CH.sub.2 -- group of which can be replaced by a cycloalkylene radical containing 3 to 7 carbon atoms, B is a straight-chained mono- or bicyclic, optionally branched, saturated or unsaturated alkylene chain containing up to 12 carbon atoms, a --CH.sub.2 -- group of which can be replaced by a cycloalkylene radical containing 3 to 7 carbon atoms and/or up to two --CH.sub.2 -- groups of which can be replaced by an oxygen or a sulphur atom or by an --S(.dbd.O) or --S(.dbd.O).sub.2 group, X is a valency bond, an oxygen atom or an --NR.sup.1 group, in which R.sup.1 is a hydrogen atom or a straight-chained or branched, saturated or unsaturated alkyl or nitroxyalkyl radical containing up to 6 carbon atoms or R.sup.1, together with the nitrogen atom of the --NR.sup.Type: GrantFiled: September 21, 1987Date of Patent: September 5, 1989Assignee: Boehringer Mannheim GmbHInventors: Herbert Simon, Helmut Michel, Wolfgang Bartsch, Klaus Strein
-
Patent number: 4838924Abstract: This invention relates to novel compounds of formula [I], a process for their production, and their use as a herbicide. ##STR1## wherein A represents the bond ##STR2## in which X is a hydrogen atom, a chlorine atom, a nitro group or a trifluoromethyl group;B represents a hydrogen atom, a methyl group or a methoxy group; andAr represents one member selected from the group consisting of ##STR3## in which R.sup.1 to R.sup.38, are as defined hereinafter.Type: GrantFiled: April 1, 1987Date of Patent: June 13, 1989Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Tetsuo Takematsu, Daisuke Fukuoka, Katsuya Takahashi, Isao Hashimoto
-
Patent number: 4816481Abstract: Disclosed herein is a cerebral-circulation-metabolism-function-improving agent which contains a 2,6-diphenyl-3,7-dioxabicyclo[3.3.0]octane derivative represented by the following formula as the effective ingredient: ##STR1## wherein, each of R.sub.1, R.sub.3, R.sub.4 and R.sub.6 represents a hydrogen atom or a lower alkoxyl group; each of R.sub.2 and R.sub.5 represents a hydrogen atom, a .beta.-D-glucosyl group or a hydroxyl group; and each of R.sub.7 and R.sub.8 represents an oxygen atom or two hydrogen atoms.Type: GrantFiled: July 21, 1987Date of Patent: March 28, 1989Assignee: Wakunaga Seiyaku Kabushiki KaishaInventors: Naoyuki Takasugi, Mitsuyasu Ushijima, Satoshi Inoue, Terukage Hirata
-
Patent number: 4777274Abstract: A process for the preparation of isosorbide-2-mononitrate (I) ##STR1## from isosorbide-2,5-dinitrate (II) ##STR2## The isosorbide-2,5-dinitrate (II) is treated, in a reaction medium consisting of an aqueous organic solvent, with salts of metals of low oxidation state.Isosorbide-2-mononitrate (I) is obtained with high selectivity.Type: GrantFiled: November 7, 1986Date of Patent: October 11, 1988Assignee: Consiglio Nazionale Delle Ricerche - Dinamite SpaInventors: Ottorino De Lucchi, Fabiola Filipuzzi, Giorgio Modena, Ettore Camera
-
Patent number: 4770871Abstract: A blend of mono- and dialkyl-1,4:3,6-dianhydrosorbitol is made by alkylation of 1,4:3,6-dianhydrosorbitol with dialkyl carbonate in the presence of a base catalyst. Mono- and dialkylated blends obtained therefrom are useful in plaque inhibiting dentrifice compositions.Type: GrantFiled: November 6, 1987Date of Patent: September 13, 1988Assignee: ICI Americas Inc.Inventor: James N. Greenshields
-
Patent number: 4769379Abstract: Dianhydrohexites of the formula ##STR1## wherein R.sup.1 is hydrogen or benzyl, R.sub.2 is alkyl or omega-theophyllin-7-yl-alkyl, and R.sup.1 and R.sub.2 together with the nitrogen atom to which they are attached form a bicyclic group and R.sup.3 is hydrogen, acyl, pyridylcarbonyl, nitro or a hydroxylamino group, are formed by an analogous method and used as pharmaceuticals in the treatment of heart and circulatory diseases.Type: GrantFiled: July 2, 1985Date of Patent: September 6, 1988Assignee: Heinrich Mack Nachf.Inventors: Matyas Leitold, Peter Stoss
-
Patent number: 4721796Abstract: Nitrate esters of D-isoidide which are useful as cardiovascular agents, and crystalline D-isoidide from which such nitrates are derivable.Type: GrantFiled: November 14, 1986Date of Patent: January 26, 1988Inventor: Lloyl D. Hayward
-
Patent number: 4720503Abstract: N-substituted fused-heterocyclic carboxamide derivatives, for example, N-(2,2-diphenylethenyl)-3-hydroxythieno[3,2-b]thiophene-2-carboxamide can be prepared by ring closure between an appropriately substituted halo-thiophene ester, e.g., methyl 3-bromo-thiophene-2-carboxylate, and mercaptoacetamide followed by condensation with diphenylacetaldehyde. Alternatively, the ring closure can be carried out between an appropriately substituted mercaptothiophene ester, e.g., methyl 3-mercaptothiophene-2-carboxylate and a haloacetamide to afford the fused-heterocyclic intermediate, 3-hydroxythieno[3,2-b]thiophene-2-carboxamide. N-alkenylation of the intermediate will then lead to the final products.Type: GrantFiled: August 2, 1985Date of Patent: January 19, 1988Assignee: Merck & Co., Inc.Inventors: Bruce E. Witzel, Allan N. Tischler, Debra L. Allison
-
Patent number: 4713466Abstract: A selective process for the preparation of isosorbide-5-mononitrate (I) ##STR1## from isosorbide-2,5-dinitrate (II) ##STR2## Said preparation is carried out by treating isosorbide-2,5-dinitrate with a suitable reduction system in the presence of not easily oxidizable coordinating metal ions.Type: GrantFiled: May 12, 1986Date of Patent: December 15, 1987Assignees: Consiglio Nazionale Delle Richerche, DinamiteInventors: Ottorino De Lucchi, Fabiola Filippuzzi, Giorgio Modena, Ettore Camera
-
Patent number: 4708820Abstract: Phenol-type natural antioxidative materials containing analogs of sesamin or sesamolin are manufactured by processing a processed sesame speed product with an acid catalyst and subsequently condensing and separating the desired materials by a physical means such as extraction, distillation and adsorption.Type: GrantFiled: November 27, 1985Date of Patent: November 24, 1987Assignee: Takemoto Yushi Kabushiki KaishaInventors: Mitsuo Namiki, Toshihiko Osawa, Yasuko Fukuda, Tatsuhiko Ozaki
-
Patent number: 4705800Abstract: The invention relates to novel 3-phenyl-4-cyanopyrrole derivatives of the general formula ##STR1## wherein X has the following meaning: A: hydrogen or CO--R.sub.1, wherein R.sub.1 is C.sub.1 -C.sub.6 alkyl which is unsubstituted or substituted by halogen or C.sub.1 -C.sub.3 alkoxy; or is C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkylnyl, or C.sub.1 -C.sub.6 alkoxy which is unsubstituted or substituted by halogen or C.sub.1 -C.sub.3 alkoxy; or is C.sub.3 14 C.sub.6 alkenyloxy, or C.sub.3 -C.sub.6 cycloalkyl;B: S--R.sub.2, wherein R.sub.2 is C.sub.1 -C.sub.3 haloalkyl;C: CH(Y)R.sub.3, wherein R.sub.3 is hydrogen or C.sub.1 -C.sub.8 haloalklyl and Y is hydroxy, halogen or OC(O)R.sub.4, wherein R.sub.4 is C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 haloalkyl, C.sub.2 -C.sub.6 alkenyl, or C.sub.1 -C.sub.6 alkoxycarbonyl; orD: CH.sub.2 --Z, wherein Z is the group ##STR2## in which formula each of R.sub.5 and R.sub.6 independently of the other is hydrogen, C.sub.1 -C.sub.Type: GrantFiled: June 13, 1986Date of Patent: November 10, 1987Assignee: Ciba-Geigy CorporationInventors: Robert Nyfeler, Josef Ehrenfreund
-
Patent number: 4684740Abstract: This invention discloses a process for producing 2,6-bis (4-hydroxy-3,5-dimethoxyphenyl)-3,7-dioxabicyclo [3.3.0] octane, i.e. syringaresinol and stereo-isomers thereof, from plants which contain lignin with syringyl unit. The process comprises heating plant under pressure in hydrous condition, and then quickly discharging them therefrom into an environment at atmospheric pressure so as to explode into pieces and subjecting the fine pieces to extraction with organic solvent such as methanol and acetone or an alkaline solution such as sodium hydroxide and purification. Syringaresinols are useful like ginseng as a tonic.Type: GrantFiled: March 18, 1986Date of Patent: August 4, 1987Assignee: Jujo Paper Co., Ltd.Inventors: Takayoshi Higuchi, Mitsuhiko Tanahashi, Motoo Mastukura
-
Patent number: 4680307Abstract: A compound of the formula: ##STR1## wherein X.sup.1 is a free or an esterified carboxyl group, or a group of the formula: ##STR2## (R.sup.a and R.sup.b are each independently a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.3 -C.sub.7 cycloalkyl group, a benzyl group, a phenyl group, a phenyl group substituted with a halogen atom or a C.sub.1 -C.sub.4 alkyl group, or, when taken together with the adjacent nitrogen atom to which they are attached, they represent a 5 to 7 membered saturated heterocyclic group, Y.sup.1 is a group of the formula: ##STR3## (R.sup.6 is a hydrogen atom or C.sub.1 -C.sub.4 alkyl group), ##STR4## (R.sup.6 is as defined above), ##STR5## R.sup.1 is a hydrogen atom, a hydroxyl group or a protected hydroxyl group, R.sup.2 is a hydrogen atom or R.sup.1 and R.sup.2, when taken together, mean a shingle linkage to from a double bond between the carbon atoms which they are linked, R.sup.3 is a hydroxyl group or a protected hydroxyl group, R.sup.4 is a hydrogen atom or a C.sub.1 -C.sub.Type: GrantFiled: January 26, 1984Date of Patent: July 14, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Masami Muraoka, Toshio Nakamura, Akihiko Sugie, Keiichi Ono, Michihiro Yamamoto
-
Patent number: 4659846Abstract: In a process for the preparation of 2,5-diloweralkyl-1,4; 3,6-dianhydrosorbitols by reacting 1,4;3,6-dianhydrosorbitol with an alkylating agent in an alkaline aqueous-organic solvent solution, the improvement comprising using a tertiary alkanol as the organic solvent.Type: GrantFiled: May 2, 1986Date of Patent: April 21, 1987Assignee: Rutgerswerke AktiengesellschaftInventors: Manfred Maurer, Winfried Orth, Werner Fickert
-
Patent number: 4613638Abstract: Novel phenolic compounds derived from hexides are disclosed which are useful stabilizers of synthetic polymer resins.Type: GrantFiled: August 19, 1985Date of Patent: September 23, 1986Assignee: ICI Americas Inc.Inventors: John F. Stephen, Jerry H. Smith, Makram H. Meshreki
-
Patent number: 4584391Abstract: A novel and efficient method is proposed for the preparation of isosorbide-5-nitrate which is a promising medicinal compound for several diseases due to disorder in heart. The method comprises direct nitration of isosorbide with a concentrated nitric acid in a specific reaction medium containing an aromatic hydrocarbon solvent, e.g. benzene, in addition to conventional acetic acid and acetic anhydride. After neutralization of the reaction mixture and removal of the dinitrate as a byproduct therefrom, the reaction mixture is admixed with an aqueous solution of sodium hydroxide so that a sodium salt of isosorbide-5-nitrate is precipitated in the form of a hydrate, which is a novel compound not known in the prior art. This hydrate sodium salt is then decomposed with an acid to give the desired isosorbide-5-nitrate in a high yield.Type: GrantFiled: November 23, 1984Date of Patent: April 22, 1986Assignee: Toshin Chemical Co. Ltd.Inventors: Toshio Itoh, Susumu Ishiguro, Fumitake Shimada, Kenichi Ishibashi
-
Patent number: 4564692Abstract: A simplified economical process is provided for preparing pure anhydro sugar alcohols by a controlled crystallization from concentrated aqueous solutions or melts containing these alcohols. These pure anhydro sugar alcohols are useful as polyol components in making polyester and polyurethane polymers.Type: GrantFiled: July 18, 1983Date of Patent: January 14, 1986Assignee: CPC International Inc.Inventors: John Feldmann, Hubert Koebernick, Klaus Richter, Hans-Ulrich Woelk
-
Patent number: 4542137Abstract: Alkylaminodesoxy-1.4;3.6-dianhydrohexitol nitrates substituted by purine bases of the general formula I, ##STR1## wherein R.sup.1 signifies a hydrogen atom or a lower alkyl group with 1 to 4 C-atoms, X a straight-chained or branched alkyl or hydroxyalkyl group with 1 to 7 C-atoms, Y a 1,3-dialkylxanthin-7-yl or a 3,7-dialkylxanthin-1-yl group, each with straight or branched-chained alkyl groups with 1 to 5 C-atoms, or an adenin-9-yl group, as well as their physiologically acceptable acid-addition salts. Process for the preparation of said compounds and pharmaceutical compositions containing said compounds.Type: GrantFiled: July 20, 1981Date of Patent: September 17, 1985Assignee: Dr. Willmar Schwabe GmbH & Co.Inventors: Klaus Klessing, Shyam S. Chatterjee
-
Patent number: 4506086Abstract: Liquid dianhydrohexitol mixtures are prepared from diacylation products of hexitols and compounds such as organic carboxylic acids, carboxylic acid anhydrides, carboxylic acid halides, ketene and carbonic acid ester derivatives. More specifically, such diacylation products are simultaneously dehydrated and isomerized by subjecting them to a temperature of at least 130.degree. C. in the presence of a strong acid to yield diacylated dianhydrohexitol isomer mixtures. These isomer mixtures are then converted to dianhydrohexitol isomer mixtures by hydrolysis or transesterification. Suitable strong acids include proton acids, Lewis acids and heterogeneous acid catalysts (e.g., ion exchange resins). The mixtures of the present invention are characterized by a minimal tendency towards crystallization. These mixtures are particularly useful as chain extending agents in the production of polyurethanes.Type: GrantFiled: July 20, 1983Date of Patent: March 19, 1985Assignee: Bayer AktiengesellschaftInventors: Herbert Salzburg, Manfred Hajek, Holger Meyborg
-
Patent number: 4479951Abstract: 1.4;3.6-Dianhydrohexitol nitrates substituted by purine bases, namely, adenyl-desoxy-1.4;3.6-dianhydrohexitol nitrates of the general formula Ia as well as theophyllinyl-desoxy-1.4;3.6-dianhydrohexitol nitrates of the general formula Ib, ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and, independently of one another signify(a) a hydrogen atom,(b) a straight-chained or branched alkyl group with 1 to 7 C-atoms,(c) an .omega.-phenylalkyl group, whereby the alkyl group has 1 to 7 C-atoms and whereby the phenyl ring can be halogen-substituted in the p-position, or wherein(d) R.sup.1 signifies one of the residues given under (a) to (c) and R.sup.2 an acyl radical or an aliphatic, possibly methyl-substituted monocarboxylic acid with 2 to 7 C-atoms, or wherein(e) R.sup.1 and R.sup.Type: GrantFiled: July 20, 1981Date of Patent: October 30, 1984Assignee: Dr. Willmar Schwabe GmbH & Co.Inventors: Klaus Klessing, Shyam S. Chatterjee
-
Patent number: 4435586Abstract: A high yield process for the polyalkylation of hexitols and hexitol inner ethers is presented wherein aqueous dispersions of monoalkali metal alkoxides thereof in organic solvent are reacted with alkyl monohalides to first form the monoalkylated hexitols or hexitol inner ether and thereafter further alkylated by addition of reactants to form the completely alkylated derivative.Type: GrantFiled: April 28, 1982Date of Patent: March 6, 1984Inventors: Walter M. Kruse, John F. Stephen
-
Patent number: 4431830Abstract: In a process for preparing isosorbide-5-nitrate, isosorbide is reacted with an aliphatic carboxylic acid, with the formation of an acylation mixture. The acylation mixture is then nitrated, and the resulting nitration mixture is hydrolyzed and/or transesterified in order to split off acyl groups. The product is used in treatment of angina pectoris.Type: GrantFiled: April 23, 1982Date of Patent: February 14, 1984Assignee: Cassella AktiengesellschaftInventor: Karl Schonafinger
-
Patent number: 4431829Abstract: The present invention provides a process for the preparation of 1,4:3,6-dianhydro-D-glucitol-5-nitrate, in which(a) 1,4:3,6-dianhydro-D-glucitol is acetylated with 0.5 to 1.5 mole equivalents of acetic anhydride in the presence of a catalyst, a mixture of 1,4:3,6-dianhydro-D-glucitol-2-acetate, 1,4:3,6-dianhydro-D-glucitol-5-acetate and 1,4:3,6-dianhydro-D-glucitol-2,5-diacetate being obtained;(b) the mixture is nitrated with nitric acid, a mixture of 1,4:3,6-dianhydro-D-glucitol-2-acetate-5-nitrate and 1,4:3,6-dianhydro-D-glucitol-5-acetate-2-nitrate being obtained; and(c) hydrolysis is carried out with an inorganic base to give 1,4:3,6-dianhydro-D-glucitol-5-nitrate;wherein, in step (a), the reaction is carried out in the presence of a basic catalyst and the 1,4:3,6-dianhydro-D-glucitol-2,5-diacetate is substantially removed before further working up.Type: GrantFiled: June 24, 1981Date of Patent: February 14, 1984Assignee: Boehringer Mannheim GmbHInventors: Einhart Kiegel, Karl Lauer
-
Patent number: 4417065Abstract: A process for the preparation of isosorbide-2-nitrate of the formula ##STR1## comprising contacting isosorbide with a carboxylic acid anhydride in the presence of a metal salt; esterifying the resultant isosorbide-5-acylate with nitric acid; and converting the resultant isosorbide-5-acylate-2-nitrate to isosorbide-2-nitrate by treatment with an alkyl alcohol in the presence of an alkali metal alcoholate.Type: GrantFiled: May 24, 1982Date of Patent: November 22, 1983Assignee: Heinrich Mack Nachf. Chem.-Pharmazeutische FabrikInventor: Peter Stoss
-
Patent number: 4413122Abstract: Aminodesoxy-1.4;3.6-dianhydrohexitol derivatives of the general formula I, ##STR1## wherein R.sup.1 and R.sup.2, in each case independently of one another, signifies a hydrogen atom or a lower alkyl group with 1 to 4 C-atoms or wherein R.sup.1 signifies a hydrogen atom and R.sup.2 an adamant(1)yl radical or wherein R.sup.1 and R.sup.2, together with the nitrogen atom to which they are attached, (a) signify the residue of a cyclic, non-aromatic secondary amine possibly containing a further hetero atom or (b) the aden(9)yl radical possibly mono- or disubstituted on the 6-amino group or (c) the 6-alkylmercaptopurin(9)yl radical or (d) the theophyllin(7)yl radical or (e) the 6-chloropurin-9-yl radical or wherein R.sup.1 signifies a hydrogen atom or a lower alkyl group with 1 to 4 C-atoms and R.sup.2 an .omega.-theophyllin(7)ylalkyl radical or an .omega.-theobromin-1-ylalkyl radical or an .omega.Type: GrantFiled: July 20, 1981Date of Patent: November 1, 1983Assignee: Fa. Wilmar Schwabe GmbH & Co.Inventor: Klaus Klessing
-
Patent number: 4408061Abstract: A process for the preparation of 1,4-3,6-dianhydro-hexitols from hexitols by elimination of water is described, characterized in that gaseous hydrogen halide is used as the acid dehydrating agent optionally with carboxylic acids, carboxylic acid halides and/or carboxylic acid anhydrides in quantities of up to 600 mol percent, based on the hexitols, as cocatalysts. The reaction is carried out in the absence of water and organic solvents, preferably using gaseous hydrogen chloride, temperatures of up to 300.degree. C. and pressures of up to 250 bar. Very high yields are obtained after working up of the product by distillation or extraction.Type: GrantFiled: March 11, 1982Date of Patent: October 4, 1983Assignee: Bayer AktiengesellschaftInventors: Herbert Salzburg, Holger Meyborg, Heinz Ziemann
-
Patent number: 4381400Abstract: The invention relates to the synthesis of isosorbide mononitrates.The process according to the invention consists in reacting a hydrazine derivative with isosorbide dinitrate, in a polar solvent medium. The reaction is preferably carried out at the reflux temperature of the solvent medium, with an excess of the hydrazine derivative. A preferred solvent medium is a mixture of tetrahydrofuran and methanol. The process leads to the preferential formation of isosorbitol-2-mononitrate, which is a coronary vasodilator.Type: GrantFiled: February 16, 1982Date of Patent: April 26, 1983Assignee: Societe Nationale Des Poudres et ExplosifsInventors: Jean-Marie Emeury, Eric Wimmer
-
Patent number: 4371703Abstract: This invention relates to a process for the production of isosorbide-5-nitrate comprising(a) subjecting an acylation mixture of isosorbide containing varying proportions of isosorbide, isosorbide-2-acylate, isosorbide-5-acylate and/or isosorbide-2,5-diacylate, or pure isosorbide-5-acylate or an equimolar mixture of isosorbide-2,5-diacylate and isosorbide to a transacylation reaction in the presence of a catalyst and removing the isosorbide-2-acylate present from the reaction mixture by fractional distillation;(b) optionally subjecting the separated isosorbide-2-acylate to a further purification step;(c) esterifying the obtained isosorbide-2-acylate with nitric acid; and(d) partially hydrolyzing the obtained isosorbide-2-acylate-5-nitrate.Type: GrantFiled: January 7, 1982Date of Patent: February 1, 1983Assignee: Heinrich Mack Nachf. Chem-Parm. FabrikInventor: Peter Stoss
-
Patent number: 4364953Abstract: 2-0- and 5-0-substituted 1.4;3.6-dianhydrohexitol mononitrates of the general formula I, ##STR1## wherein R is a halogen-substituted phenyl group, a methanesulphonyl or nicotinoyl group, as well as their physiologically acceptable acid-addition salts, insofar as R signifies the nicotinoyl group.Processes for the preparation of said compounds and pharmaceutical compositions containing said compounds.Type: GrantFiled: July 20, 1981Date of Patent: December 21, 1982Assignee: Firma Willmar SchwabeInventors: Klaus Klessing, Shyam S. Chatterjee