The Chalcogen, X, Is In A -c(=x)- Group Patents (Class 549/375)
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Patent number: 5254698Abstract: Phenyldioxanes of the formula I ##STR1## wherein R.sup.1 is an alkyl or alkenyl residue each with up to 16 C atoms, wherein one or two non-adjacent CH.sub.2 groups of these residues may be replaced by --CO--O-- or --O--CO--,Q.sup.1 and Q.sup.2 are each independently ##STR2## L.sup.1 and L.sup.2 are each independently F or H, and Y is Cl, F, CN, CF.sub.3, OCF.sub.3 or OCF.sub.2 H,m and n is 0 or 1,are suitable as components of liquid crystal media.Type: GrantFiled: February 12, 1991Date of Patent: October 19, 1993Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: David Coates, Simon Greenfield, Graham Smith, Volker Reiffenrath, Joachim Krause, Herbert Plach
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Patent number: 5248793Abstract: An improved process for the preparation of (4R-cis)-1,1-dimethylethyl 6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate is described where a hydroxy ester derivative is converted in two steps to the desired product, as well as valuable intermediates used in the process.Type: GrantFiled: December 21, 1992Date of Patent: September 28, 1993Assignee: Warner-Lambert CompanyInventors: Alan Millar, Donald E. Butler
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Patent number: 5231197Abstract: Ethylenically unsaturated graftable monomers are prepared by reacting hydroxy substituted orthoesters with electrophilic reagents, an alkaline reagent, and a phase transfer catalyst. Preferably the hydroxy orthoester is 4-hydroxymethyl-2-methoxy-2-methyl-1,3-dioxolane, and the preferred reagent is acryloyl chloride with sodium hydroxide as the base and methyltrialkylammonium (C.sub.8-10) chloride as the phase transfer catalyst.Type: GrantFiled: June 1, 1992Date of Patent: July 27, 1993Assignee: General Electric CompanyInventors: Farid F. Khouri, Robert J. Halley
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Patent number: 5217991Abstract: Non-peptidyl compounds characterized generally as cycloalkyl/cycloalkylalkyl-N-terminal cycloalkoxy-C-terminal amino hydroxy .beta.-amino acid derivatives are useful as renin inhibitors for treatment of hypertension. Compounds of particular interest are of the formula ##STR1## wherein R.sub.1 is selected from cycloalkyl and cycloalkylalkyl groups, wherein said cycloalkyl group contains three to about eight carbon atoms and the acyclic alkyl portion of said cycloalkylalkyl group contains one to about eight carbon atoms; wherein each of R.sub.2 and R.sub.4 is independently selected from hydrido and methyl; wherein R.sub.3 is methyl or ethyl: wherein R.sub.5 is cyclohexylmethyl; wherein R.sub.6 and R.sub.Type: GrantFiled: May 28, 1992Date of Patent: June 8, 1993Assignee: G. D. Searle & Co.Inventors: Gunnar J. Hanson, John S. Baran, Dave Weissing, Mark Russell
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Patent number: 5216013Abstract: Non-peptidyl compounds characterized generally as heterocyclic acyl aminodiol .beta.-amino acid derivatives are useful as renin inhibitors for treatment of hypertension. Compounds of particular interest are compounds of the formula ##STR1## wherein R.sub.1 is selected from aryl and aralkyl groups represented by ##STR2## and wherein R.sub.1 may be further selected from heteroaryl and heteroaralkyl represented by ##STR3## wherein each of T and A is independently selected from N and CH; wherein n is a number selected from zero through five, inclusive; wherein X is selected from oxygen atom, methylamino and NH; wherein each of Y and Z is independently selected from chloro, fluoro, methoxy and dimethylamino; wherein Q is oxygen atom; and wherein each of T and A is independently selected from N and CH; wherein each of R.sub.2 and R.sub.4 is independently selected from hydrido and methyl; wherein R.sub.3 is selected from methyl and ethyl; wherein R.sub.5 is cyclohexylmethyl; wherein R.sub.6 is hydroxy; wherein R.Type: GrantFiled: July 16, 1992Date of Patent: June 1, 1993Assignee: G. D. Searle & Co.Inventor: Gunnar J. Hanson
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Patent number: 5214197Abstract: A novel 2,4-dihydroxyadipic acid derivative of the formula: ##STR1## wherein R.sup.1 and R.sup.4 are the same or different and each a hydrogen atom, an alkyl group, an aralkyl group, an aryl group or a silyl group, and R.sup.2 and R.sup.3 are the same or different and each a hydrogen atom or a protective group of a hydroxy group or together form a ring, which is useful as a common intermediate in the synthesis of HMG-CoA reductase inhibitor.Type: GrantFiled: July 2, 1991Date of Patent: May 25, 1993Assignee: Kanegafuchi Chemical Industry Co., Ltd.Inventors: Shigeo Hayashi, Noboru Ueyama, Kenji Inoue, Teruyoshi Koga, Satomi Takahashi
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Patent number: 5189180Abstract: Seco-mevinic acid derivatives are provided which have the structure ##STR1## including all stereoisomers thereof, wherein Z is ##STR2## R is H, alkali metal or lower alkyl, R.sup.1 is H, lower alkyl, aryl, lower alkoxy, cycloalkyl, heteroaryl, aralkyl, heteroaralkyl or heterocyclic; R.sup.2 is lower alkyl, cycloalkyl or aralkyl, and X is O or NR.sup.5 wherein R.sup.5 is H or lower alkyl, and are HMG CoA reductase inhibitors and thus are useful as antihypercholesterolemic agents and in treating atherosclerosis.New intermediates for preparing the above seco-mevinic acid derivatives are also provided.Type: GrantFiled: May 1, 1991Date of Patent: February 23, 1993Assignee: E. R. Squibb & Sons, Inc.Inventor: Donald S. Karanewsky
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Patent number: 5171471Abstract: Novel ferroelectric and antiferroelectric liquid crystal compounds of the invention, which comprise those showing optically tristable states in phase S*.sub.(3), have a wide range of phase transition temperature so as to be not only preferably used solely as display element material but also mixed with any other liquid crystal to desiredly expand the above range wider and make optical response time faster.Typical compounds are represented by ##STR1## in which Z means CF.sub.3, C.sub.2 F.sub.5, CHF.sub.2, CH.sub.2 F, CClF.sub.2, CCl.sub.2 F, CF.sub.3 CCl.sub.2 or C.sub.3 F.sub.7, m' and n' are same or different with each other and each is an integer of 1-20.Type: GrantFiled: January 31, 1992Date of Patent: December 15, 1992Assignee: Showa Shell Sekiyu K.K.Inventors: Yoshiichi Suzuki, Takashi Hagiwara, Koichi Numazawa
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Patent number: 5169960Abstract: The invention relates to a process for the production of E/Z mixtures of 2-(bicyclo[3.3.0]octan-3-ylidene)-acetic acid derivatives of Formula I, ##STR1## in which either the E or the Z portion predominates.Type: GrantFiled: September 12, 1991Date of Patent: December 8, 1992Assignee: Schering AktiengesellschaftInventors: Hartmut Rehwinkel, Helmut Vorbruggen, Hans-Joachim Gais, Gerhard Schmiedl, Jorg Bund
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Patent number: 5162571Abstract: Novel phenol derivatives of the general formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, X, Y and n are as defined in the specification, which have therapeutic and prophylactic activities against cerebral, cardiac, renal and pulmonary circulatory system diseases, respiratory diseases, allergy, anaphylactic shock, endotoxin shock, inflammation and the like as well as inhibiting activities against vascularization by oncocytes.Type: GrantFiled: June 8, 1988Date of Patent: November 10, 1992Assignee: Takeda Chemical Industries, Ltd.Inventors: Mitsuru Shiraishi, Kohei Mishikawa
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Patent number: 5162552Abstract: A process for the preparation of 4-acetals of butene-1,4-dial of the formula ##STR1## where R is an alkyl, alkenyl, cycloalkyl or aralkyl radical of 1 to 12 carbon atoms which may contain alkoxy groups, or the two radicals R together form an alkylene or alkenylene radical of 2 to 10 carbon atoms which may contain alkoxy groups, and R.sup.1 is an alkyl, alkenyl or alkynyl radical of 1 to 12 carbon atoms which may be substituted by cycloaliphatic, aromatic or heterocyclic radicals or by hydroxyl, ether, thioether, acyl, alkylamino, carboxyl or carbalkoxy groups, or is an unsubstituted or substituted aryl radical or an alkoxy, alkylthio or acyloxy group, wherein a glyoxal monoacetal of the formula ##STR2## is reacted with an aldehyde of the formulaR.sup.1 --CH.sub.2 --CHO IIIat up to 150.degree. C., and novel acetals of butene-1,4-dial.Type: GrantFiled: April 30, 1987Date of Patent: November 10, 1992Assignee: BASF AktiengesellschaftInventors: Franz Merger, Rolf Fischer, Hans Horler, Juergen Frank
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Patent number: 5162573Abstract: 2-Propyl-2-pentanoic acid (valproic acid) esters and (E)-2-propyl-2-pentenoic acid [(E)-2-valproenoic acid] esters surprisingly proved to have valuable properties, in that they show anticonvulsive and antiepileptic activities comparable with those of valproic acid, as well as an improved bioavailability and a markedly reduced toxicity.Type: GrantFiled: June 17, 1987Date of Patent: November 10, 1992Assignee: Chiesi Farmaceutici S.p.A.Inventors: Paolo Chiesi, Vittorino Servadio, Flavio Villani
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Patent number: 5159117Abstract: A process for preparing .alpha.,.alpha.-dialkoxy ketones of the formula I ##STR1## where R.sup.1 and R.sup.2 are each, independently of one another, hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.3 -C.sub.20 -cycloalkyl, C.sub.4 -C.sub.30 -cycloalkylakyl, C.sub.9 -C.sub.30 -alkylcycloalkyl, unsubstituted or C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy-, halogen-, C.sub.1 -C.sub.4 -haloalkyl-, C.sub.1 -C.sub.4 -haloalkoxy-, phenyl-, phenoxy-, halophenyl-, halophenoxy- and/or cyano-substituted aryl, C.sub.7 -C.sub.20 -aralkyl or heterocyclyl,R.sup.2 is also ##STR2## R.sup.3 and R.sup.4 are each, independently of one another, C.sub.1 -C.sub.20 -alkyl, C.sub.3 -C.sub.20 -cycloalkyl, aryl, C.sub.7 -C.sub.20 -arylalkyl, or together are an unsubstituted or C.sub.1-C.sub.4 -alkyl- substituted C.sub.2 -C.sub.7 -alkylene chain andR.sup.5 is R.sup.1 or together with R.sup.1 is an unsubstituted or C.sub.1 -C.sub.4 -alkyl-substituted C.sub.2 -C.sub.Type: GrantFiled: August 20, 1991Date of Patent: October 27, 1992Assignee: BASF AktiengesellschaftInventors: Guenter Wegner, Stefan Karbach, Hubert Smuda, Eckhard Hickmann, Reiner Kober, Rainer Seele, Thomas Zierke
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Patent number: 5128479Abstract: Oxidized diphenylheteroalkanes of the formula I ##STR1## where R.sup.1 to R.sup.6 and A have the meanings specified in the description, and the preparation thereof are described. The substances are suitable for controlling diseases and as cosmetic agents.Type: GrantFiled: January 29, 1990Date of Patent: July 7, 1992Assignee: BASF AktiengesellschaftInventors: Bernd Janssen, Hans-Heiner Wuest
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Patent number: 5126368Abstract: The invention describes the novel compound 6(Z)-8-([2,4,5-cis]-4-o-hydroxyphenyl-2-trifluoromethyl-1,3-dioxan-5-yl)oc tenoic acid of formula I and its pharmaceutically acceptable salts and pharmaceutical compositions, which are of value in treating certain pulmonary and/or vascular disorders. Also described are various processes for the manufacture of the novel compound and intermediates for use therein.Type: GrantFiled: August 10, 1990Date of Patent: June 30, 1992Assignee: Imperial Chemical Industries plcInventor: Michael J. Smithers
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Patent number: 5118866Abstract: Polyene aldehydes of the general formula I ##STR1## where R is ##STR2## where R' is alkyl, aryl, aralkyl or cycloalkyl and, if desired, may be further substituted, and the radicals R" are each C.sub.1 -C.sub.4 -alkyl or together form --CH.sub.2 --CH.sub.2 -- or --CH.sub.2 --CH.sub.2 --CH.sub.2 -- bridges which, if desired, may be further substituted by C.sub.1 -C.sub.4 -alkyl, are prepared by catalytic oxidation of the corresponding polyene alcohol with oxygen or an oxygen-containing gas by a process wherein the oxidation is carried out in the presence of the catalyst system comprising 2,2,6,6-tetramethylpiperidine 1-oxide or 4-oxo-2,2,6,6-tetramethylpiperidine 1-oxide and copper(I) chloride.Type: GrantFiled: February 5, 1988Date of Patent: June 2, 1992Assignee: BASF AktiengesellschaftInventors: Guenter H. Knaus, Joachim Paust
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Patent number: 5103024Abstract: An improved process for the preparation of (4R-cis)-1,1-dimethylethyl 6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate is described where a hydroxy ester derivative is converted in two steps to the desired product, as well as valuable intermediates used in the process.Type: GrantFiled: October 17, 1990Date of Patent: April 7, 1992Assignee: Warner-Lambert CompanyInventors: Allan Millar, Donald E. Butler
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Patent number: 5100577Abstract: A ferroelectric liquid crystalline mixture containing at least one optically active compound of the general formula ##STR1## wherein X.sup.1 denotes a single covalent bond, --COO--, --OOC--, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 -- or --CH.sub.2 O--; one of rings A.sup.1, A.sup.2 and A.sup.3 represents trans-m-dioxan-2,5-diyl and the other two of rings A.sup.1, A.sup.2 and A.sup.3 each independently represent unsubstituted 1,4-phenylene or 1,4-phenylene substituted with cyano, halogen or lower alkyl; R.sup.1 and R.sup.2 each independently signify an optionally halogen-substituted alkyl group with up to 18 carbon atoms in which optionally 1 CH.sub.2 group or 2 non-adjacent CH.sub.2 groups is/are replaced by --O--, --CO--, --COO-- and/or --OOC--,as well as novel compounds falling under formula I and ferroelectric electrode-optical indicating devices including same.Type: GrantFiled: January 11, 1990Date of Patent: March 31, 1992Assignee: Hoffman-La Roche Inc.Inventors: Richard Buchecker, Hans-Jurgen Fromm, Stephen Kelly, Martin Schadt, Alois Villiger
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Patent number: 5093363Abstract: A 2,4,6-substituted phenol having the formula (I): ##STR1## wherein X is S or CH.sub.2 ; R.sup.1 and R.sup.2 are the same or different from each other and each is a lower alkyl group; R.sup.3 is a group of the formula: ##STR2## in which R.sup.4 is hydrogen atom or a lower alkyl group; R.sup.5 and R.sup.6 are the same or different from each other and each is hydrogen atom, a lower alkyl group, or a phenyl group which may be substituted,or a pharmaceutically acceptable salt thereof is useful as an active agent in a pharmaceutical composition. The pharmaceutical composition comprises a therapeutically effective amount of a compound having the formula (I), as an effective ingredient, in association with a pharmaceutically acceptable substantially nontoxic carrier or excipient. The pharmaceutical composition can be useful in the treatment of lipemia of mammals. Additionally the compounds can be used as antiatherosclerotic agents and antilipenic agents.Type: GrantFiled: August 14, 1990Date of Patent: March 3, 1992Assignee: Shionogi & Co., Ltd.Inventors: Toru Kita, Hiroshi Harada, Eiichi Ohsugi, Toshiro Konoike
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Patent number: 5072002Abstract: Processes of synthesizing compounds of the formula: ##STR1## wherein R.sub.1 is H, lower alkyl (1 to 6 C), lower dialkyl (1 to 6 C), lower cycloalkyl (3 to 7 C), or lower dicycloalkyl (3 to 7 C);R.sub.2 is H, lower alkyl (1 to 6 C), or lower cycloalkyl (3 to 7 C);R.sub.5 C(O) is an acyl group with R.sub.5 being alkyl (1 to 18 C), cycloalkyl, bicycloalkyl, tricycloalkyl, alkenyl (1 to 18 C), alkadienyl (1 to 18 C), aryloxy-, alkoxy-, substituted alkyl, wherein the substituents are acetoxy-, acyl-, alkoxy-, alkoxycarbonyl-, alkylamido-, alkylsulfonyl-, alkylsulfoxido-, alkylthio-, alkylthiocarbonyl-, amino-, aroyl-, aryl-, aryloxy-, arylthio-, azido-, carboxy-, dialkylamido-, dialkylamino-, dihalogeno-, hydroxy-, monohalogeno-, trihalogeno-, or arylalkylthio-.Compounds of the above formula are capable of appreciably lowering blood levels of cholesterol in human beings.Type: GrantFiled: July 18, 1989Date of Patent: December 10, 1991Assignee: The Governors of the University of AlbertaInventors: Derrick L. J. Clive, Andrew G. H. Wee, Kammaralli S. K. Murthy
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Patent number: 5072008Abstract: The invention concerns a novel process for the stereospecific manufacture of novel hydroxymethyl lactols of the formula I by a one step reduction of a corresponding lactone carboxylic ester of the formula II (many of which esters are novel) using a reducing agent such as diisobutylaluminium hydride at about ambient temperature. The lactols of formula I are intermediates for the production of pharmacologically active 1,3-dioxane alkenoic acids useful in the treatment of certain cardiovascular and pulmonary medical conditions. Certain of the esters of formula II are novel and are also included in the invention.Type: GrantFiled: June 14, 1989Date of Patent: December 10, 1991Assignee: Imperial Chemical Industries PLCInventor: Gregory D. Harris
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Patent number: 5059698Abstract: Polymeric .beta.-keto-ester acetals which, in combination with compounds which release acid under the action of actinic radiation, are suitable as positive photoresists, which are suitable for the production of printing plates, printed circuit boards, integrated circuits or silver-free films, can be prepared by free-radical polymerization from compounds of the formula I or II ##STR1## in which n is zero, 1 or 2 and, for example, R.sup.1 is an H atom, C.sub.1 -C.sub.10 -alkyl, phenyl or benzyl, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 independently of one another are each an H atom, halogen atom, C.sub.1 -C.sub.10 alkyl, phenyl, naphthyl or the radical --COOR.sup.9, ##STR2## or --SO.sub.2 R.sup.9, in which R.sup.9 is C.sub.1 -C.sub.6 alkyl or phenyl, X is O, S or NR.sup.10, in which R.sup.10 is an H atom, C.sub.1 -C.sub.6 alkyl or phenyl, Y is a radical of the following formulae ##STR3## in which R.sup.11 is an H atom, C.sub.1 -C.sub.Type: GrantFiled: June 9, 1989Date of Patent: October 22, 1991Assignee: Ciba-Geigy CorporationInventors: Adrian Schulthess, Max Hunziker
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Patent number: 5053507Abstract: Optical active compounds of the formula (1), (2), (3) and (4): ##STR1## The compounds (1), (2) and (3) are useful as raw materials of chiral dopants to be added for forming liquid crystal compositions, medicines or agricultural chemicals, and the compound (4) is useful as chiral dopants to be added for forming liquid crystal compositions.Type: GrantFiled: March 21, 1990Date of Patent: October 1, 1991Assignee: Arakawa Kagaku Kogyo Kabushiki KaishaInventors: Fumio Moriuchi, Hiroshi Yano, Kazushige Kajita
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Patent number: 5047412Abstract: The invention describes novel (2-styryl-, 2-naphthyl- and 2-phenethyl-4-o-hydroxyphenyl-1,3-dioxan-5-yl)alkenoic acids and related tetrazoles and sulphonamides, of the formula I wherein Q completes a benzene or pyridine ring, Y is vinylene, Z is carboxy, 1(H)-tetrazol-5-yl or a group of the formula --CO.NHSO.sub.2 R.sup.6, and R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, A.sup.1, A.sup.2, n and m have the meanings defined in the specification, and pharmaceutically acceptable salts thereof, for use in conjunction with their pharmaceutical compositions in treating certain pulmonary and/or vascular disorders. The invention also describes various processes and intermediates for the manufacture of the novel compounds.Type: GrantFiled: February 1, 1989Date of Patent: September 10, 1991Assignee: Imperial Chemical Industries PLCInventors: George R. Brown, Michael J. Smithers
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Patent number: 4999378Abstract: Phenylcarboxylic acid derivatives having the formula: ##STR1## wherein R.sup.1 and R.sup.2 are each H, halogen, alkyl, haloalkyl, alkanoyl, cycloalkyl, nitro, amino, --O--D--R.sup.5 (D is alkylene, R.sup.5 is H, amino, morpholino, carboxyl, phthalimido, phenyl, epoxy), substituted or unsubstituted phenoxy, substituted or unsubstituted phenylalkylamino, carboxylalkenyl, or both form alkylenedioxy; R.sup.3 is H, --E--R.sup.6 (E is alkylene, R.sup.6 is H, carboxyl, cyano, OH, phenylalkoxy, or halogen-substituted phenyl, or phenylcarbamoyl), --CO--G--R.sup.7 (G is alkylene, R.sup.7 is H, substituted or unsubstituted phenylcarbamoyl), substituted or unsubstituted benzoyl, alkenyl, carbamoyl, phenyl, or halophenyl; R.sup.4 is H or alkyl; A is alkylene, alkylene condensed with cycloalkyl ring, or alkenylene; B is alkylene or alkenylene; l is 0 or 1.Type: GrantFiled: June 20, 1989Date of Patent: March 12, 1991Assignee: Otsuka Pharmaceutical Company, LimitedInventors: Setsuro Fujii, Hiroyuki Kawamura, Shinichi Watanabe
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Patent number: 4983759Abstract: A compound of a 3,5,6-trihydroxyhexanoic acid derivative of the formula: ##STR1## wherein P.sup.1 and P.sup.2 are independently hydrogen atoms or hydroxy-protecting groups, or together form a ring, and R is an alkyl group is effectively prepared by a process comprising steps of:reacting a butyronitrile derivative of the formula: ##STR2## wherein P.sup.1 and P.sup.2 are the same as defined above with an .alpha.-haloacetate of the formula:X--CH.sub.2 --COOR (III)wherein X is a halogen atom, and R is the same as defined above in the presence of a metallic catalyst selected from the group consisting zinc and zinc-copper to form a keto acid derivative of the formula: ##STR3## wherein P.sup.1, P.sup.2 and R are the same as defined above, and then reducing the obtained keto-acid derivative of the formula (IV).Type: GrantFiled: December 20, 1989Date of Patent: January 8, 1991Assignee: Kanegafuchi Chemical Industry Co., Ltd.Inventors: Kenji Inoue, Satomi Takahashi, Keiichi Yonetsu, Noboru Ueyama
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Patent number: 4981993Abstract: The invention concerns new polyfunctional ethylenic monomers of the general formula (I): ##STR1## where R=cyano, substituted or unsubstituted acyl, substituted or unsubstituted alkoxycarbonyl or substituted or unsubstituted aryloxycarbonyl; R.sub.1 and R.sub.2 each represent --CHR.sub.3 R.sub.4 where R.sub.3 and R.sub.4 may be identical or different and represent H or an alkyl, alkenyl or aralkyl group. R.sub.1 and R.sub.2 may, alternatively, together form a radical --CH.sub.2 --(CR.sub.5 R.sub.6).sub.n --CHR.sub.7 where n=0 or 1 and R.sub.5, R.sub.6 and R.sub.7 may be identical or different and represent H or CH.sub.3.Particular monomers are: 2-cyano-4,4-dimethoxy-3-hydroxy-1-butene; 2-cyano-4,4-dibutoxy-3-hydroxy-1-butene; 4,4-dibutoxy-2-ethoxycarbonyl-3-hydroxy-1-butene; 2-butoxycarbonyl-4,4-dibutoxy-3-hydroxy-1-butene; 4,4-dimethoxy-2-hydroxythoxycarbonyl-1-butene; 4,4-dimethoxy-2-dimethylaminoethoxycarbonyl -3-hydroxy-1-butene; and 4,4-dimethoxy-2-ethoxycarbonyl-3-hydroxy-1-butene.Type: GrantFiled: August 18, 1988Date of Patent: January 1, 1991Assignee: Societe Francaise HoechstInventors: Didier Wilhelm, Alain Blanc
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Patent number: 4982006Abstract: The present invention involves process for the preparation of compounds having the chemical structure: ##STR1## wherein Ar--H is an aromatic compound which is activated to an electrophilic attack, and wherein --Y is an aliphatic group having a labile moiety, especially where the labile moiety is a terminally unsaturated moiety: --C.tbd.CH, ##STR2## or aldehydes in the form of their acetals. The process comprises the step of reacting Ar--H and ##STR3## wherein --X is --Cl or --Br, and where the reaction step is carried out in a solvent medium at a temperature of from about -40.degree. C. to about -100.degree. C. using stannic chloride as a catalyst.Type: GrantFiled: May 1, 1989Date of Patent: January 1, 1991Assignee: Norwich Eaton Pharmaceuticals, Inc.Inventor: Thomas T. Hudec
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Patent number: 4977279Abstract: A process for the preparation of optically active 3-demethylmevalonic acid derivatives of the formula I ##STR1## (3,5-dihydroxy carboxylic acid derivatives) or of the formula II ##STR2## in which R, R.sup.1 and Y have the indicated meanings, is described. The invention furthermore relates to aldehydes of the formula XII ##STR3## in which M represents the indicated protective groups.Type: GrantFiled: November 20, 1989Date of Patent: December 11, 1990Assignee: Hoechst AktiengesellschaftInventors: Gunther Wess, Kurt Kesseler, Ekkehard Baader, Gerhard Beck
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Patent number: 4962207Abstract: The present application discloses novel potassium salts of particular tellurium and selenium compounds which are useful for the stimulation of the production of cytokines.Type: GrantFiled: October 9, 1987Date of Patent: October 9, 1990Assignee: Bar-Ilan UniversityInventors: Michael Albeck, Benjamin Sredni
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Patent number: 4943588Abstract: Prodrugs of 3-hydroxy-3-methylglutarylcoenzyme A (HMG-CoA) reductase inhibitors which are useful as antihypercholesterolemic agents and are represented by the following general structural formula (I): ##STR1## are disclosed.Type: GrantFiled: February 1, 1989Date of Patent: July 24, 1990Assignee: Merck & Co., Inc.Inventors: Wasyl Halczenko, Steven M. Pitzenberger, George Hartman
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Patent number: 4943384Abstract: Cyclohexane derivatives of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --R.sup.2 IwhereinR.sup.1 and R.sup.2 are each H or an alkyl group which has 1-10 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or --CO-groups, and/or --CO--O-- groups and/or --CH.dbd.CH-- groups, or are F, Cl, Br, CN or R.sup.3 --A.sup.3 --Z.sup.2 --,A.sup.1 is --A--, A.sup.4 --Z.sup.o --A-- or --A--Z.sup.o --A.sup.4 --,A is a trans-1,4-cyclohexylene or 1,4-cyclohexenylene group which is unsubstituted or is monosubstituted or polysubstituted in the 2-, 3-, 5- and/or 6-position by F and/or Cl and/or Br and/or CN and/or an alkyl group or a fluorinated alkyl group each of which has 1-10 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or --CO-- groups and/or --CO--O-- groups, which trans-1,4-cyclohexylene or 1,4-cyclohexenylene group can optionally also be substituted in the 1-position and/or 4-position and one or two CH.sub.Type: GrantFiled: November 21, 1986Date of Patent: July 24, 1990Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Wolfgang Sucrow, Herbert Wolter, Rudolf Eidenschink
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Patent number: 4940806Abstract: Novel substituted 2-(1H-1,2,4-triazolyl)-1-phenylethan-1-one ketals of the general formula ##STR1## wherein one of the two phenyl substituents is in 2-position and the other is in 4-position, and wherein R.sub.a is halogen, methyl or C.sub.1 -C.sub.3 haloalkoxy, and U and V are each independently of the other C.sub.1 -C.sub.12 alkyl, unsubstituted or substituted by halogen or C.sub.1 -C.sub.6 alkoxy, or together are an alkylene bridge selected from ##STR2## wherein R.sub.1 to R.sub.5 are as defined herein, and the acid addition salts and metal complex salts, have microbicidal properties and are especially suitable for controling phytopathogenic microorganisms. They can be used in the form of plant protective or seed dressing agents for preventing or controlling plant pathogens.Type: GrantFiled: June 21, 1989Date of Patent: July 10, 1990Assignee: Ciba-Geigy CorporationInventor: Adolf Hubele
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Patent number: 4929739Abstract: A novel complex of a class of tellurium and selenium compounds is disclosed, which is based on a complexing agent and the particular compound to be complexed.Type: GrantFiled: March 24, 1988Date of Patent: May 29, 1990Assignee: Bar-Ilan UniversityInventors: Benjamin Sredni, Leo Pavliv, Michael Albeck
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Patent number: 4921979Abstract: the invention concerns novel 1,3-dioxane ethers of the formula I, wherein R.sup.1 includes alkyl, cycloalkyl, pheny and phenylalkyl, R.sup.2 R.sup.3 include hydrogen and alkyl, n is 1 or 2, m is 2, 3 or 4, p is zero, 1 or 2, and Z is carboxy or 1(H)-tetrazol-5-yl, and pharmaceutically acceptable salts thereof, for use in conjunction with their pharmaceutical compositions in the treatment of certain pulmonary and/or vascular disorders. The invention also describes various processes and intermediates for the manufacture of the novel compounds.Type: GrantFiled: July 13, 1988Date of Patent: May 1, 1990Assignee: Imperial Chemical Industries plcInventor: Michael J. Smithers
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Patent number: 4902712Abstract: The invention describes the novel compound 4(Z)-6-([2,4,5-cis]-4-o-hydroxyphenyl-2-trifluoromethyl-1,3-dioxan-5-yl)he xenoic acid of formula I and its pharmaceutically acceptacle salts and pharmaceutical compositions, which are of value in treating certain pulmonary and/or vascular disorders. Also described are various processes for the manufacture of the novel compound and intermediates for use therein.Type: GrantFiled: May 9, 1986Date of Patent: February 20, 1990Assignee: Imperial Chemical Industries plcInventor: Michael J. Smithers
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Patent number: 4900846Abstract: The invention provides a novel process for making novel (4-phenyl-1,3-dioxan-cis-5-yl)alkenoic acids of the formula I in which Ra and Rb are independently hydrogen, alkenyl, alkyl, halogenoalkyl, pentafluorophenyl, aryl or aryl-(1,4C)alkyl; or Ra and Rb together are polymethylene; Rc is hydroxy or (1-6C)alkanesulphonamideo, A is vinylene, n is 1, Y is polymethylene, and benzene ring B bears various optional substituents. The process involves the reaction of an aldehyde of formula II with an ylid to give an erythro-diol of formula III which is then cyclized to the required dioxane derivative of formula I. The invention also provides a novel process for making the aldehydes of formula II from the corresponding lactols of formula IIa, which are themselves obtained with the correct trans-stereochemistry by two selective reductions of a trans-phenylparaconic acid of formula V. The compounds of formula I are useful as thereapeutic agents.Type: GrantFiled: October 27, 1987Date of Patent: February 13, 1990Assignee: Imperial Chemical Industries plcInventor: Gregory P. Harris
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Patent number: 4895962Abstract: The invention provides a novel group of 4(Z)-([2,4,5-cis]-2,4-diphenyl-1,3-dioxan-5-yl)hexenoic acids of formula I, wherein X is F, Cl, Br, CF.sub.3, CN, CH.sub.3 O or NO.sub.2 and one of Y and Z is hydrogen or fluoro and the other is hydrogen, and their pharmaceutically acceptable salts; together with their pharmaceutical compositions for use in treating a variety of disease conditions. Also provided are methods for the manufacture of novel compounds. Representative compounds are those in which X is 2-cyano or 2-chloro and Y and Z are both hydrogen.Type: GrantFiled: July 13, 1988Date of Patent: January 23, 1990Assignee: Imperial Chemical Industries plcInventors: Andrew G. Brewster, George R. Brown, Michael J. Smithers
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Patent number: 4895963Abstract: The invention provides a novel group of 4(Z)-6-([2,4,5-cis]-2-alkyl-4-o-hydroxyphenyl-1,3-dioxan-5-yl)hexenoic acids of formula I wherein R is branched alkyl or 3-5 carbon atoms and one of X and Y is hydrogen or fluoro and the other is hydrogen, and their pharmaceutically acceptable salts; together with their pharmaceutical compositions for use in treating a variety of disease conditions. Also provided are methods for the manufacture of the novel compounds. A representative compound is that in which R is t-butyl and X and Y are both hydrogen.Type: GrantFiled: July 12, 1988Date of Patent: January 23, 1990Assignee: Imperial Chemical Industries plcInventors: Andrew G. Brewster, Michael J. Smithers
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Patent number: 4883887Abstract: A process for producing carotenoids and carotenoid intermediates via reduction of sulfonyl polyenes with a dithionite in the presence of ammonia or an aliphatic amine, including novel intermediates in this process, which carotenoids are known coloring agents for foodstuffs, animal feeds, pharmaceuticals, etc.Type: GrantFiled: July 1, 1988Date of Patent: November 28, 1989Assignee: Hoffmann-La Roche Inc.Inventors: Kurt Bernhard, Stephan Jaggli, Paul Kreienbuhl, Ulrich Schwieter
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Patent number: 4877891Abstract: 1,1-dialkoxy- or 1,1-(.alpha.,.omega.-methylenedioxy)-non-2-yn-9-ol and their OH-protected derivatives of the general formula I ##STR1## where R.sup.1 and R.sup.2 are each C.sub.1 -C.sub.6 -alkyl or together form an alkylene chain of 2 to 5 carbon atoms and X is hydrogen or a protective group which can be eliminated, their preparation and their use as intermediates.Type: GrantFiled: August 5, 1988Date of Patent: October 31, 1989Assignee: BASF AktiengesellschaftInventors: Rainer Becker, Walter Seufert, Ernst Buschmann, Christiane Bruchner
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Patent number: 4876368Abstract: A process is provided for the production of a monohydroxy monocyclic acetal, e.g., trimethylolpropane cyclic formal, of a trihydroxy alcohol, e.g., trimethylolpropane, and an aldehyde, e.g., formaldehyde, by subjecting a "heavier condensation product" of the trihydroxy alcohol and the aldehyde than the desired cyclic acetal, i.e., one having a higher molecular weight and boiling point, to acetal formation conditions. In a preferred embodiment, the product of reaction of the trihydroxy alcohol and aldehyde is treated to remove the desired monohydroxy monocyclic acetal product and at least part of the remainder comprising the heavier condensation product is recycled to the reaction together with a flesh supply of trihydroxy alcohol and aldehyde. The monohydroxy monocyclic acetal product may be further reacted to obtain a desired ester, e.g. trimethylolpropane cyclic formal acrylate, such as by transesterifying the acetal with a low boiling ester of the esterifying acid, e.g.Type: GrantFiled: May 24, 1988Date of Patent: October 24, 1989Assignee: Hoechst Celanese CorporationInventors: Jerry A. Broussard, Wayne C. Fuqua, James H. George
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Patent number: 4846998Abstract: Cyclohexane derivatives of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --R.sup.2 Iin whichR.sup.1 and R.sup.2 are each an alkyl group having 1-10 C atoms, in which one or two non-adjacent CH.sub.2 groups can also be replaced by O atoms and/or --CO-- groups and/or --CO--O-- groups and/or --CH.dbd.CH-- groups, one of the radicals R.sup.1 and R.sup.2 also being H, F, Cl, Br, CN or R.sup.3 --A.sup.3 --Z.sup.2 --,A.sup.1 is --A--, A.sup.4 --A-- or --A--A.sup.4 --,A is a trans-1,4-cyclohexylene group which can be substituted in the 2-, 3-, 5- and/or 6-position one or more times by F and/or Cl and/or Br and/or CN and/or an alkyl group or a fluorinated alkyl group which each have 1-10 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or --CO-- groups and/or --CO--O-- groups, and which may also be substituted in the 1- and/or 4-position,A.sup.2, A.sup.3 and A.sup.Type: GrantFiled: November 21, 1986Date of Patent: July 11, 1989Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Ludwig Pohl, Bernhard Scheuble, Reinhard Hittich, Rudolf Eidenschink, Hans A. Kurmeier, Andreas Wachtler
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Patent number: 4845119Abstract: A compound of the formula ##STR1## wherein X has the formula --CR.sup.5 .dbd.CR.sup.6 --, --C.tbd.C-- or ##STR2## wherein ring A is phenyl, naphthyl or heterocyclic; wherein R.sup.1 is hydrogen, alkyl, alkanoyl or aroyl;wherein R.sup.2, R.sup.3 and R.sup.4, which may be the same or different, each is an electron withdrawing substituent of each is hydrogen or alkyl, alkoxy or dialkylamino, provided that when ring A is phenyl or naphthyl at least one of R.sup.2, R.sup.3 and R.sup.4 is an electron-withdrawing substitutent;wherein R.sup.5 and R.sup.6, each is hydrogen, halogeno or alkyl;wherein R.sup.7 is alkyl or halogenoalkyl; and wherein R.sup.8 has the formula --Y--Q--R.sup.9 wherein Y is straight- or branched-chain alkylene or alkenylene; wherein Q is --O--, --S--, --SO-- or --SO.sub.2 --; andwherein R.sup.9 is alkyl or up to 6 carbon atoms which contains one or more defined substituents, processes for their manufacture and pharmaceutical compositions containing them.Type: GrantFiled: February 18, 1986Date of Patent: July 4, 1989Assignee: Imperial Chemical Industries PLCInventors: Leslie R. Hughes, Howard Tucker
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Patent number: 4843171Abstract: 1,1-Dialkoxy-2-methyl-4,4-diacyloxy-2-butenes having the general structure: ##STR1## in which R.sub.1 represents alkyl substituents having from 1 to 5 carbon atoms, or both R.sub.1 substituents together represent a single ethylene or propylene substituent, or a single C.sub.1 -C.sub.2 alkyl substituent, and R.sub.2 represents alkyl substituents having from 1 to 5 carbon atoms, or cycloalkyl substituent having from 5 to 7 carbon atoms, or aromatic substituents (preferably phenyl substituents). These new compounds are useful as building blocks in the synthesis of terpenes and carotenoids.Type: GrantFiled: July 1, 1987Date of Patent: June 27, 1989Assignee: BASF AktiengesellschaftInventors: Bernhard Schulz, Rolf Fischer
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Patent number: 4837205Abstract: Prodrugs of 3-hydroxy-3-methylglutarylcoenzyme A (HMG-CoA) reductase inhibitors which are useful as antihypercholesterolemic agents and are represented by the following general structural formula (I): ##STR1## are disclosed.Type: GrantFiled: September 2, 1986Date of Patent: June 6, 1989Assignee: Merck & Co., Inc.Inventors: Wasyl Halczenko, George Hartman, Steven M. Pitzenberger
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Patent number: 4834905Abstract: Compounds of the formulaR.sup.1 --Q.sup.1 --(CH.sub.2).sub.m --(COO).sub.n --(CH.sub.2).sub.p --Q.sup.2 --R.sup.2whereinR.sup.1 and R.sup.2 are each independently alkyl or alkoxy each of 1-12 C atoms, F, Cl, Br, CN or --Q.sup.3 --R.sup.3, or one of R.sup.1 and R.sup.2 can also be H;Q.sup.1, Q.sup.2 and Q.sup.3 are each independently 1,4-phenylene, 1,4-cyclohexylene, 1,4-bicyclo(2,2,2)-octylene or 1,3-dioxane-2,5-diyl, each of which is unsubstituted or substituted by 1-4 fluorine, chlorine or bromine atoms;R.sup.3 is alkyl or alkoxy each of 1-8 C atoms, H, F, Cl, Br or CN;m is 1, 2, 3, 4, 5 or 6; n is 0 or 1; and p is 0, 1, 2, 3, 4 or 5; the sum of (m+p) being 2, 4 or 6 and the sum of (m+n+p) being at least 3;but with the proviso that Q.sup.3 is unsubstituted 1,4-phenylene or 1,4-phenylene substituted by a fluorine, chlorine or bromine atom, only when n=1 or (m+p)=6 or at least one of R.sup.1 to R.sup.3 is F, Cl or Br or none of R.sup.1 to R.sup.3 is CN or two of the radicals R.sup.1 to R.sup.Type: GrantFiled: October 3, 1986Date of Patent: May 30, 1989Assignees: Merck Patent Gesellschaft mit beschrankter Haftung, The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: Rudolf Eidenschink, Joachim Krause, Beatrice M. Andrews, George W. Gray, Neil Carr
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Patent number: 4826620Abstract: The new esters derived from a chiral compound containing two OH groups and at least one mesogenic carboxylic acid which have the general formula (I) ##STR1## in which X.sup.1 =O--H or O--CO--(C.sub.1 to C.sub.12)alkyl and X.sup.2 =O--MC or X.sup.1 and X.sup.2 denote O-MC independently of each other, where MC is the molecular radical of a mesogenic monocarboxylic acid after splitting off an OH group.The esters or esters substituted in the aromatic part of the phenolic part preferably find application as an admixture intwistable liquid crystal phases in which they produce a temperature compensation and a high degree of twisting.Type: GrantFiled: January 21, 1988Date of Patent: May 2, 1989Assignee: Hoechst AktiengesellschaftInventors: Gerd Heppke, Detlef Lotzsch, Feodor Oestreicher, Gunter Scherowsky
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Patent number: 4824858Abstract: The invention describes novel (2-styryl-, 2-naphthyl- and 2-phenethyl-4-o-hydroxyphenyl-1,3-dioxan-5-yl)alkenoic acids and related tetrazoles and sulphonamides, of the formula I wherein Q completes a benzene or pyridine ring, Y is vinylene, Z is carboxy, 1 (H)-tetrazol-5-yl or a group of the formula --CO.NHSO.sub.2 R.sup.6, and R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, A.sup.1, A.sup.2, n and m have the meanings defined in the specification, and pharmaceutically acceptable salts thereof, for use in conjunction with their pharmaceutical compositions in treating certain pulmonary and/or vascular disorders. The invention also describes various processes and intermediates for the manufacture of the novel compounds.Type: GrantFiled: May 9, 1986Date of Patent: April 25, 1989Assignee: Imperial Chemical Industries PLCInventors: George R. Brown, Michael J. Smithers
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Patent number: 4822815Abstract: The invention concerns novel 1,3-dioxane hexenoic aids and related carboxytic acid esters and alkanesulphonamides of the formula I in which X is oxy or thio, R.sup.1 is hydrogen, halogeno, trifluoromethyl, cyano or nitro and R.sup.2 is hydrogen, together with their pharmaceutically acceptable salts. The invention also concerns processes for the production of the novel compounds and pharmaceutical compositions containing the compounds for use in the treatment of various diseases in which thromboxane A.sub.2 (TXA.sub.2) is implicated.Type: GrantFiled: December 10, 1986Date of Patent: April 18, 1989Assignee: Imperial Chemical Industries PLCInventors: George R. Brown, Michael J. Smithers