Acyclic -c(=x)-, Wherein X Is Chalcogen, Containing Patents (Class 549/342)
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Patent number: 8933117Abstract: To provide potassium salts of substituted cycloalkene derivatives, which suppress the production of an inflammatory mediator caused by intracellular signal transduction or cell activation induced by endotoxin, and crystals thereof. The present invention provides potassium (2-chloro-4-fluorophenyl){[(2R,3R,8R)-7-(ethoxycarbonyl)-2,3-bis(hydroxymethyl)-1,4-dioxaspiro[4.5]deca-6-en-8-yl]sulfonyl}azanide and potassium (2-bromo-4-fluorophenyl){[(2R,3R,8R)-7-(ethoxycarbonyl)-2,3-bis(hydroxymethyl)-1,4-dioxaspiro[4.5]deca-6-en-8-yl]sulfonyl}azanide, each of which suppresses the production of an inflammatory mediator caused by intracellular signal transduction or cell activation induced by endotoxin, crystals thereof, and a pharmaceutical containing any of the same, and a prophylactic and/or therapeutic agent for sepsis containing any of the same.Type: GrantFiled: September 22, 2011Date of Patent: January 13, 2015Assignee: Daiichi Sankyo Company, LimitedInventors: Nobuyuki Ohkawa, Kouki Iida, Takayoshi Nagasaki
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Publication number: 20140371468Abstract: The present invention relates to a novel process for the preparation of 1-H-pyrrolidine-2,4-dione derivatives and to novel intermediates and to a process for their preparation.Type: ApplicationFiled: August 29, 2014Publication date: December 18, 2014Inventors: Reiner FISCHER, Thomas HIMMLER
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Publication number: 20140256731Abstract: Pleuromutilin derivative compounds of the following formula, and uses thereof for the treatment of diseases mediated by microbes, are disclosed:Type: ApplicationFiled: May 21, 2014Publication date: September 11, 2014Applicant: NABRIVA THERAPEUTICS AGInventors: Rosemarie MANG, Werner HEILMAYER, Rudolf BADEGRUBER, Dirk B. STRICKMANN, Rodger NOVAK, Mathias FERENCIC, Atchyuta Rama Chandra Murty BULUSU
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Publication number: 20140114080Abstract: A fluorinated monomer has formula (1) wherein R1 is H, F, methyl or trifluoromethyl, R2 and R3 are H or a monovalent hydrocarbon group, R4 to R6 each are a monovalent fluorinated hydrocarbon group, A is a divalent hydrocarbon group, and k1 is 0, 1 or 2. A polymer derived from the fluorinated monomer may be endowed with appropriate water repellency, water slip, acid lability and hydrolysis and is useful as an additive polymer in formulating a resist composition.Type: ApplicationFiled: December 27, 2013Publication date: April 24, 2014Applicant: SHIN-ETSU CHEMICAL CO., LTD.Inventors: Masayoshi SAGEHASHI, Koji HASEGAWA, Takeshi SASAMI
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Publication number: 20140088158Abstract: The present invention relates to compounds of the formula I, wherein A, Y, Z, R20 to R22 and R50 have the meanings indicated in the claims, which are valuable pharmaceutical active compounds. Specifically, they are inhibitors of the endothelial differentiation gene receptor 2 (Edg-2, EDG2), which is activated by lysophosphatidic acid (LPA) and is also termed as LPA1 receptor, and are useful for the treatment of diseases such as atherosclerosis, myocardial infarction and heart failure, for example. The invention furthermore relates to processes for the preparation of the compounds of the formula I, their use and pharmaceutical compositions comprising them.Type: ApplicationFiled: November 27, 2013Publication date: March 27, 2014Applicant: SANOFIInventors: Josef PERNERSTORFER, Heinz-Werner KLEEMANN, Matthias SCHAEFER, Alena SAFAROVA, Marcel PATEK
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Publication number: 20140073689Abstract: To provide potassium salts of substituted pyrrolidine derivatives, which suppress the production of an inflammatory mediator caused by intracellular signal transduction or cell activation induced by endotoxin, and crystals thereof. The present invention provides potassium(2-chloro-4-fluorophenyl){[(2R,3R,8R)-7-(ethoxycarbonyl)-2,3-bis(hydroxymethyl)-1,4-dioxaspiro[4.5]deca-6-en-8-yl]sulfonyl}azanide and potassium(2-bromo-4-fluorophenyl){[(2R,3R,8R)-7-(ethoxycarbonyl)-2,3-bis(hydroxymethyl)-1,4-dioxaspiro[4.5]deca-6-en-8-yl]sulfonyl}azanide, each of which suppresses the production of an inflammatory mediator caused by intracellular signal transduction or cell activation induced by endotoxin, crystals thereof, and a pharmaceutical containing any of the same, and a prophylactic and/or therapeutic agent for sepsis containing any of the same.Type: ApplicationFiled: September 22, 2011Publication date: March 13, 2014Applicant: DAIICHI SANKYO COMPANY, LIMITEDInventors: Nobuyuki Ohkawa, Kouki Iida, Takayoshi Nagasaki
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Patent number: 8618096Abstract: Methods and compositions for treating disease caused by increased iron levels are disclosed Fluoregenic compounds and methods of using the same are also described.Type: GrantFiled: July 21, 2009Date of Patent: December 31, 2013Assignee: The Regents of the University of CaliforniaInventors: Adam Renslo, Sumit Mahajan
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Patent number: 8618312Abstract: Production of a bicyclo[3.1.0]hexane derivative, useful as a metabotropic glutamate receptor modulator, becomes possible by a production method that includes converting a compound represented by Formula (II) into a compound represented by Formula (III) by reaction with an acyl group donor in the presence of a microorganism-derived enzyme, without using an expensive optically active trans hydroxy ester as a starting material and without employing a fluorination reaction requiring an ultralow temperature reaction. Furthermore, since asymmetric synthesis can be carried out in a stage closer to the final product, the production method is useful as a production method that can mass produce a bicyclo[3.1.0]hexane derivative.Type: GrantFiled: November 19, 2010Date of Patent: December 31, 2013Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Mitsuaki Hirotsuka, Joji Sasaki, Hiroaki Kamiyama, Motoko Oshida, Takaaki Ishii
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Publication number: 20130211104Abstract: The present invention relates to a new process for the preparation of 6-hydroxy-5-arylbicyclo[2.2.2]octan-2-one compounds of the formula (II); which may subsequently be further transformed to compounds of the formula (I): The present invention further relates to novel compounds as such, which compounds are useful intermediates in the above process.Type: ApplicationFiled: October 19, 2011Publication date: August 15, 2013Applicant: ACTELION PHARMACEUTICALS lTD,Inventors: Stefan Abele, Jacques-Alexis Funel
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Publication number: 20130178521Abstract: To provide potassium salts of substituted pyrrolidine derivatives, which suppress the production of an inflammatory mediator caused by intracellular signal transduction or cell activation induced by endotoxin, and crystals thereof. The present invention provides potassium(2-chloro-4-fluorophenyl){[(2R,3R,8R)-7-(ethoxycarbonyl)-2,3-bis(hydroxymethyl)-1,4-dioxaspiro[4.5]deca-6-en-8-yl]sulfonyl}azanide and potassium(2-bromo-4-fluorophenyl){[(2R,3R,8R)-7-(ethoxycarbonyl)-2,3-bis(hydroxymethyl)-1,4-dioxaspiro[4.5]deca-6-en-8-yl]sulfonyl}azanide, each of which suppresses the production of an inflammatory mediator caused by intracellular signal transduction or cell activation induced by endotoxin, crystals thereof, and a pharmaceutical containing any of the same, and a prophylactic and/or therapeutic agent for sepsis containing any of the same.Type: ApplicationFiled: September 22, 2011Publication date: July 11, 2013Applicant: DAIICHI SANKYO COMPANY, LIMITEDInventors: Nobuyuki Ohkawa, Kouki Iida, Takayoshi Nagasaki
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Patent number: 8470958Abstract: This invention is the design and synthesis of a caprolactone monomer which bears a pendant protected carboxyl group. This monomer has been copolymerized with caprolactone in varying ratios. After polymerization, the protecting group can be removed and an antibiotic can be attached as a new pendant group. The bioactivity of the antibiotic-bound poly(caprolactone) polymer is described.Type: GrantFiled: February 7, 2012Date of Patent: June 25, 2013Assignee: University of South FloridaInventors: Edward Turos, Michelle Leslie
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Publication number: 20130096322Abstract: A method of production of value-added, biobased chemicals, derivative products, and/or purified glycerin from bioglycerin of recycled oil, grease, and/or fat origin is described herein. A method of purification of bioglycerin of recycled oil, grease, and/or fat origin is also described herein. The method of purification of bioglycerin of recycled oil, grease, and/or fat origin described provides methods for desalinating, decolorizing, and/or concentrating bioglycerin of recycled oil, grease, and/or fat origin for the production of biobased chemicals, derivative products, and/or purified glycerin.Type: ApplicationFiled: January 12, 2012Publication date: April 18, 2013Applicant: THESIS CHEMISTRY, LLCInventors: John R. Peterson, Christopher M. Yost
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Publication number: 20130040954Abstract: Pleuromutilin derivative compounds of the following formula, and uses thereof for the treatment of diseases mediated by microbes, are disclosed:Type: ApplicationFiled: April 3, 2012Publication date: February 14, 2013Inventors: Rosemarie MANG, Werner HEILMAYER, Rudolf BADEGRUBER, Dirk B. STRICKMANN, Rodger NOVAK, Mathias FERENCIC, Atchyuta Rama Chandra Murty BULUSU
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Publication number: 20120302745Abstract: This application discloses a novel process for the synthesis of himbacine analogs, as well as the compounds produced thereby. The synthesis proceeds by alternative routes including the cyclic ketal amide route, the chiral carbamate amide route, and the chiral carbamate ester route. The compounds produced thereby are useful as thrombin receptor antagonists.Type: ApplicationFiled: August 2, 2012Publication date: November 29, 2012Inventors: Tiruvettipuram K. Thiruvengadam, Anantha R. Sudhakar, Ngiap Kie Lim, Daw-Iong Kwok, George G. Wu, Tao Wang, Mingsheng Huang, Michael D. Green
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Publication number: 20120190865Abstract: The present invention relates to a novel process for the preparation of 1-H-pyrrolidine-2,4-dione derivatives and to novel intermediates and to a process for their preparation.Type: ApplicationFiled: January 25, 2012Publication date: July 26, 2012Applicant: Bayer CropScience AGInventors: Reiner FISCHER, Thomas HIMMLER
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Publication number: 20120142914Abstract: This application discloses a novel process for the synthesis of himbacine analogs, as well as the compounds produced thereby. The synthesis proceeds by alternative routes including the cyclic ketal amide route, the chiral carbamate amide route, and the chiral carbamate ester route. The compounds produced thereby are useful as thrombin receptor antagonists.Type: ApplicationFiled: February 10, 2012Publication date: June 7, 2012Inventors: Tiruvettipuram K. Thiruvengadam, Anantha R. Sudhakar, Ngiap Kie Lim, Daw-Iong Kwok, George G. Wu, Tao Wang, Mingsheng Huang, Michael D. Green
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Publication number: 20120135351Abstract: The present invention provides a salt represented by the formula (I): wherein R1 and R2 independently each represent a C1-C6 alkyl group or R1 and R2 are bonded each other to form a C5-C20 aliphatic ring together with the carbon atom to which they are bonded, R3 and R4 independently each represent a fluorine atom or a C1-C6 perfluoroalkyl group, X1 represents a C1-C17 divalent saturated hydrocarbon group in which one or more —CH2— can be replaced by —O— or —CO— and which may be substituted with one or more fluorine atoms, and Z1+ represents an organic counter ion.Type: ApplicationFiled: November 25, 2011Publication date: May 31, 2012Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventors: Koji ICHIKAWA, Yukako ANRYU, Shingo FUJITA
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Patent number: 8188089Abstract: Compounds of Formula I are described: preferably subject to the proviso that either (a) R2 and R3 together form —O—CH(R10)—O—, or (b) R5 and R6 together form —O—CH(R10)—O—, wherein R10 is H, halo, or loweralkyl. Pharmaceutical salts, formulations, and methods of using the same in the treatment of cancer are also described.Type: GrantFiled: December 20, 2006Date of Patent: May 29, 2012Assignee: The University of North Carolina at Chapel HillInventors: Kuo-Hsiung Lee, Linyi Wei, Kenneth F. Bastow, Arnold Brossi, Tian-Shung Wu
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Patent number: 8110678Abstract: This invention is the design and synthesis of a caprolactone monomer which bears a pendant protected carboxyl group. This monomer has been copolymerized with caprolactone in varying ratios. After polymerization, the protecting group can be removed and an antibiotic can be attached as a new pendant group. The bioactivity of the antibiotic-bound poly(caprolactone) polymer is described.Type: GrantFiled: May 10, 2007Date of Patent: February 7, 2012Assignee: University of South FloridaInventors: Edward Turos, Michelle Leslie
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Publication number: 20110250539Abstract: A fluorinated monomer has formula (1) wherein R1 is H, F, methyl or trifluoromethyl, R2 and R3 are H or a monovalent hydrocarbon group, R4 to R6 each are a monovalent fluorinated hydrocarbon group, A is a divalent hydrocarbon group, and k1 is 0, 1 or 2. A polymer derived from the fluorinated monomer may be endowed with appropriate water repellency, water slip, acid lability and hydrolysis and is useful as an additive polymer in formulating a resist composition.Type: ApplicationFiled: April 6, 2011Publication date: October 13, 2011Inventors: Masayoshi SAGEHASHI, Koji Hasegawa, Takeshi Sasami
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Publication number: 20100267947Abstract: This application discloses a novel process for the synthesis of himbacine analogs, as well as the compounds produced thereby. The synthesis proceeds by alternative routes including the cyclic ketal amide route, the chiral carbamate amide route, and the chiral carbamate ester route. The compounds produced thereby are useful as thrombin receptor antagonists.Type: ApplicationFiled: June 30, 2010Publication date: October 21, 2010Applicant: SCHERING CORPORATIONInventors: Tiruvettipuram K. Thiruvengadam, Anantha R. Sudhakar, Ngiap Kie Lim, Daw-long Kwok, George G. Wu, Tao Wang, Mingsheng Huang, Michael D. Green
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Publication number: 20090233952Abstract: [Object] To provide a substituted cycloalkene derivative having an action to suppress intracellular signal transduction or cell activation induced by endotoxin and to suppress cell responses due to the intracellular signal transduction and cell activation such as an excess generation of inflammatory mediators such as TNF-?, pharmacologically acceptable salts therefor, a medicament containing them as an active ingredient, a preparation method therefor, and a medicament containing the aforementioned substituted cycloalkene derivative as an active ingredient which is superior in prophylaxis and/or treatment of diseases such as sepsis (septic shock, disseminated intravascular coagulation, multiple organ failure and the like), that are associated with intracellular signal transduction or cell activation induced by endotoxin and to cell responses to the intracellular signal transduction and cell activation.Type: ApplicationFiled: September 13, 2006Publication date: September 17, 2009Inventors: Tomio Kimura, Nobuyuki Ohkawa, Takayoshi Nagasaki, Atsuhiro Sugidachi, Osamu Ando
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Patent number: 7528167Abstract: A compound of formula (I) or its enantiomers or diastereoisomers thereof: wherein: A, X, W, R1, Y; R3; and R4 are as defined herein. The compounds of the invention may be used as inhibitors of the papilloma virus E1-E2-DNA complex. The invention further provides a method of treating or preventing human papilloma virus infection.Type: GrantFiled: May 12, 2006Date of Patent: May 5, 2009Assignee: Boehringer Ingelheim (Canada) Ltd.Inventors: Christiane Yoakim, William W. Ogilvie, Jeffrey O'Meara, Peter White, Nathalie Goudreau
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Patent number: 7323577Abstract: A novel process for efficiently and easily producing a compound represented by the formula: wherein ring A is a benzene ring that may be optionally further substituted in addition to the group represented by W, or a salt thereof; which comprises reacting a compound represented by the formula: wherein R1 and R2 are the same or different and each is a hydrogen atom, an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, Y is a halogen atom, ring A is a benzene ring that may be optionally further substituted in addition to the group represented by Y and ring B is an optionally substituted benzene ring, or a salt thereof, with a compound represented by the formula: WH wherein W is wherein ring C is an optionally substituted benzene ring, ring D is an optionally substituted 5- to 7-membered nitrogen-containing heterocyclic ring, R3 is a hydrogen atom, an aliphatic hydrocarbon group containing an aromatic group or an acyl group, and R4 is a hydrogen atom, an optType: GrantFiled: February 22, 2006Date of Patent: January 29, 2008Assignee: Takeda Pharmaceutical Company LimitedInventors: Hiroyuki Tawada, Makoto Yamashita, Yujiro Ono
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Patent number: 7169940Abstract: NST 400 compounds consisting of a unit for partial coordination of Ca2+ ions (CPCU). The NST 400 compounds are optionally conjugated to another pharmaceutically active compound. The compounds and conjugates can be used for affinity filters and for binding negative charged phospholipids. The compounds and conjugates can also be used for treating diseases involving changes of cell membrane asymmetry.Type: GrantFiled: October 31, 2000Date of Patent: January 30, 2007Assignee: NST Neurosurvival Technologies Ltd.Inventor: Ilan Ziv
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Patent number: 6835841Abstract: A novel process for the asymmetric synthesis of substituted cyclic &bgr;-amino-carboxylates of the type shown in the specification from appropriate &bgr;-enamino-ester starting materials is described. These compounds are useful as intermediates for MMP and TACE inhibitors.Type: GrantFiled: September 11, 2003Date of Patent: December 28, 2004Assignee: Bristol-Myers Squibb CompanyInventors: Joerg Deerberg, Douglas D. McLeod, Tai-Yuen Yue
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Publication number: 20030139376Abstract: This invention is directed to lipoxin A4 analogs of the following formula (I) and (II): 1Type: ApplicationFiled: October 22, 2002Publication date: July 24, 2003Applicant: Schering AktiengesellschaftInventors: John G. Bauman, William J. Guilford, John F. Parkinson, Werner Skuballa, Babu Subramanyam
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Patent number: 6025519Abstract: Cyclobutane-1,2-dicarboxylic esters of the formula: ##STR1## in which R.sup.1 is a C.sub.1-8 -alkyl group, an optionally substituted mono- or bicyclic cycloaliphatic group having 3 to 10 ring carbon atoms, an optionally substituted aryl or arylalkyl group or an optionally substituted saturated heterocyclic group and R.sup.2 is either C.sub.1-4 -alkyl or both radicals R.sup.2 together form a group of the formula --(CH.sub.2).sub.n --(n is 2 to 4), are prepared from the corresponding maleic or fumaric esters and ketene acetals in the presence of a Lewis acid and a sterically hindered base. The reaction is stereoselective when optically active maleic or fumaric esters are employed. The cyclobutane-1,2-dicarboxylic esters (I), in particular those having trans configuration, are intermediates in the synthesis of pharmaceutically active compounds.Type: GrantFiled: July 20, 1998Date of Patent: February 15, 2000Assignee: Lonza, Ltd.Inventor: Andreas Brunner
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Patent number: 5962704Abstract: A method for producing an amide derivative of the formula ?XV! ##STR1## wherein each symbol is as defined in the specification, and an enantiomer thereof, a novel intermediate useful for producing said compound and a production method thereof. The production method of the present invention is extremely easy and simple as compared to the conventional methods, and enables effective production of compound ?XV! at high yields, which includes compound ?XVI! having an HIV protease inhibitory action. In addition, the novel intermediates of the present invention are extremely useful as intermediates for producing not only the aforementioned compound ?XVI! but also compounds useful as X-ray contrast media.Type: GrantFiled: March 25, 1998Date of Patent: October 5, 1999Assignees: Japan Tobacco Inc., Agouron Pharmaceuticals, Inc.Inventors: Takashi Inaba, Yasuki Yamada
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Patent number: 5861421Abstract: This invention relates to derivatives of 4,4-(disubstituted)cyclohexan-1-ones and related compounds which are useful for treating allergic and inflammatory diseases.Type: GrantFiled: June 23, 1997Date of Patent: January 19, 1999Assignee: SmithKline Beecham CorporationInventors: Siegfried B. Christensen, IV, Joseph M. Karpinski, M. Dominic Ryan, Paul E. Bender
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Patent number: 5773614Abstract: (1R,trans) Diprotected 3-methylene-1,2-cyclopropanedimethanol is oxidized to an optically active diol ##STR1## which is then cyclized to an orthoester ##STR2## This orthoester is then treated with a Lewis acid catalyst to give the cyclobutanone ##STR3## which is useful as an intermediate in the preparation of the antiviral agent ?1R-(1.alpha.,2.beta.,3.alpha.)!-2-amino-9-?2,3-bis(hydroxymethyl)cyclobut yl!-1,9-dihydro-6H-purin-6-one.Type: GrantFiled: September 13, 1996Date of Patent: June 30, 1998Assignee: Bristol-Myers Squibb Co.Inventors: Jollie D. Godfrey, Jr., Richard H. Mueller
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Patent number: 5559252Abstract: The present invention provides a process for the preparation of compounds of formula (V) below, and analogs thereof, which are useful as intermediates for the synthesis of HIV protease inhibitors, including cyclic ureas.Type: GrantFiled: June 30, 1994Date of Patent: September 24, 1996Assignee: The DuPont Merck Pharmaceutical CompanyInventor: Robert F. Kaltenbach III
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Patent number: 5418254Abstract: A class of 2,3-substituted cyclopenta-2,4-dienyl compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula II: ##STR1## wherein each of R.sup.1 and R.sup.2 is independently selected from hydrido, lower alkyl, lower hydroxyalkyl, halo, lower haloalkyl, lower alkoxycarbonyl and carboxyl; and wherein each of R.sup.3 through R.sup.12 is independently selected from hydrido, halo, lower alkyl, lower alkylthio, cyano, hydroxyl, mercapto, lower haloalkyl, lower haloalkoxy, lower alkoxy, lower hydroxyalkyl, lower alkoxyalkyl, lower alkylsulfonyl, lower haloalkylsulfonyl and sulfamyl; provided R.sup.5 and R.sup.10 are not both hydrido or methoxy; or a pharmaceutically suitable salt or prodrug thereof.Type: GrantFiled: May 4, 1994Date of Patent: May 23, 1995Assignee: G. D. Searle & Co.Inventors: Horng-Chih Huang, David R. Reitz
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Patent number: 5416225Abstract: The present invention provides two basic routes for the total synthesis of taxol having the structure: ##STR1## The present invention also provides the intermediates produced in the above processes, processes for synthesizing these intermediates as well as analogs to taxol. Both the intermediates and analogs to taxol may prove to be valuable anticancer agents.Type: GrantFiled: March 30, 1992Date of Patent: May 16, 1995Assignee: Sloan-Kettering Institute for Cancer ResearchInventors: Samuel J. Danishefsky, William G. Bornmann, Yves Queneau, Thomas V. Magee, Walter J. Krol
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Patent number: 5384077Abstract: Described are novel reversible photochromic naphthopyran compounds, examples of which are compounds substituted at the 3 position of the pyran ring with (i) an aryl substituent and (ii) a phenyl substituent having a 5- or 6-member heterocyclic ring fused at the number 3 and 4 carbon atoms of the phenyl substituent. Also described are organic host materials that contain or that are coated with such compounds. Articles such as ophthalmic lenses or other plastic transparencies that incorporate the novel naphthopyran compounds or combinations thereof with complementary photochromic compounds, e.g., spiro(indoline) type compounds, are also described.Type: GrantFiled: June 21, 1993Date of Patent: January 24, 1995Assignee: Transitions Optical, Inc.Inventor: David B. Knowles
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Patent number: 5344962Abstract: Cyclobutane intermediates wherein the absolute stereochemistry is (1S,2R) of the formula ##STR1## are disclosed. These intermediates are useful in the preparation of compounds having anti-viral activity.Type: GrantFiled: May 10, 1993Date of Patent: September 6, 1994Assignee: E. R. Squibb & Sons, Inc.Inventor: Saleem Ahmad
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Patent number: 5283346Abstract: Alcohols of the formula ##STR1## wherein R.sup.1 and R.sup.2 are each independently methyl or ethyl or together signify pentamethylene, formed by the enzymatic hydrolysis of a corresponding (RS) alkanoic acid ester are intermediates for Vitamin E.Type: GrantFiled: December 14, 1992Date of Patent: February 1, 1994Assignee: Hoffmann-La Roche Inc.Inventors: Richard Barner, Josepf Hubscher, Beat Wirz
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Patent number: 5202444Abstract: Optically active diols and hydroxycarboxylic acids and their esters are produced by deriving 1L-1,2:5,6-di-O-cyclohexylidene-chiro-inositol from 1L-chiro-inositol as an asymmetric source, followed by introduction of a selected class of sterically hindering and asymmetrically reactive groups into the first-mentioned compound and by subsequent reduction of the resulting compound. Seven specific inositols are also derivable from synthesis of those ultimate compounds.Type: GrantFiled: November 21, 1991Date of Patent: April 13, 1993Assignee: The Yokohama Rubber Co., Ltd.Inventors: Shoichiro Ozaki, Takahiko Akiyama, Kunio Kageyama, Morihisa Machida
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Patent number: 5179213Abstract: A process of separating one or more seleced species of ions from a solution containing the ions comprises contacting the solution with a novel composition of matter comprising a hydrocarbon chain covalently bonded to a macrocyclic compound, wherein the macrocyclic compound has at least four --A--C--C-- linkages in which A for each such linkage, is independently selected from the group consisting of O, O--CH.sub.2, S, SH.sub.2, NR, and NRCH.sub.2, with R being independently selected from the group consisting of hydrogen, alkyl and benzyl, and wherein the hydrocarbon chain has an end group ##STR1## with X being independently selected from the group consisting of lower alkyl, benzyl, phenyl, halogen, O--CH.sub.3, O--C.sub.2 H.sub.5 and O-matrix, and with matrix being independently selected from the group consisting of silica, silica gel, glass, glass fibers, titania, zirconia, alumina and nickle oxide.Type: GrantFiled: May 1, 1990Date of Patent: January 12, 1993Assignee: Brigham Young UniversityInventors: Jerald S. Bradshaw, Reed M. Izatt, Virginia B. Christensen, Ronald L. Bruening
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Patent number: 5164519Abstract: A process is disclosed for preparing a 2,2-R.sub.1, R.sub.2 -1,3-dioxolane-4-carboxylic acid or salt thereof rich in either the R or S enantiomer which process comprisesa) preparing a solution which contains a non-racemic mixture of R and S enantiomer of a carboxylate of the formula ##STR1## and M.sup.n+ ions, wherein R.sub.1 and R.sub.2 are each, independently, H or an unsubstituted or substituted alkyl group, or R.sub.1 and R.sub.2, together with the carbon atom to which they are attached, form an unsubstituted or substituted carbocyclic ring, and M is an alkali metal, an alkaline earth metal, a group IIb metal, boron, or an ammonium, di- or tri-alkanolammonium ion having 2 or 3 carbon atoms or a tetra C.sub.1 -C.sub.16 alkyl ammonium ion, and n is the valency of M;b) reducing the solubility of the M.sup.n+ salt of compound (I); andc) separating the resulting crystals from the mother liquor.Type: GrantFiled: December 2, 1991Date of Patent: November 17, 1992Assignee: Shell Internationale Research Maatschappij B.V.Inventors: Hubertus G. M. Walraven, Paulus B. M. Groen, Everardus J. A. M. Leenderts
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Patent number: 5104995Abstract: The invention is concerned with the preparation of 2-[4-(3-oxo- cyclohexyl)phenyl] propionic acid and of its derivatives. This preparation consists in transforming 4-(3,3-ethylenedioxo- cyclohexyl) acetophenone or its derivatives of the general formula: ##STR1##in which A.sup.1 represents a group ##STR2##and B represents a group ##STR3##and R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, which can be identical or different, represent each a hydrogen or an alkyl group into the desired compound of the general formula: ##STR4##in which A.sup.4 represents a group ##STR5##This method offers the advantage of being easier to implement on an industrial scale and of having a better yield than the methods of preparation of the compounds of formula (I) according to prior art.Type: GrantFiled: November 20, 1989Date of Patent: April 14, 1992Assignee: Sochinaz, Societe Chimique de Viomaz S.A.Inventor: Akhtar Haider
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Patent number: 5098932Abstract: The invention concerns a cyclic ether derivative of the formula I, ##STR1## wherein Ar.sup.1 is optionally substituted phenyl or naphthyl;A.sup.1 is (1-6C)alkylene, (3-6C)alkenylene, (3-6C)alkynylene or cyclo(3-6C)alkylene;Ar.sup.2 is optionally substituted phenylene, or a 6 membered heterocyclene moiety containing up to three nitrogen atoms;R.sup.1 and R.sup.2 together form a group of the formula --A.sup.2 --X--A.sup.3 -- wherein each of A.sup.2 and A.sup.3 is (1-6C)alkylene and X is oxy, thio, sulphinyl, sulphonyl or imino; andR.sup.3 is (1-6C)alkyl, (2-6C)alkenyl, (2-6C)alkynyl or substituted (1-4C)alkyl;or a pharmaceutically-acceptable salt thereof.The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.Type: GrantFiled: December 22, 1989Date of Patent: March 24, 1992Assignee: Imperial Chemical Industries PLC, ICI PharmaInventor: Annie Hamon
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Patent number: 5010101Abstract: Fungicidally active compounds of the formula ##STR1## in which X represents oxygen or sulphur,R represents cycloalkyl, or represents optionally substituted aryl, or represents the radical ##STR2## R.sup.1 and R.sup.2 each independently is hydrogen or an organic radical, or together with the nitrogen atom form a heterocyclic radical,R.sup.3 represents hydrogen, alkyl or optionally substituted aryl, andR.sup.4 represents alkyl or cycloalkyl, or represents optionally substituted aryl,but wherein R.sup.3 and R.sup.4 may not simultaneously represent methyl,and acid addition salts thereof, as well as intermediates therefor.Type: GrantFiled: August 17, 1989Date of Patent: April 23, 1991Assignee: Bayer AktiengesellschaftInventors: Wolfgang Kramer, Joachim Weissmuller, Dieter Berg, Wilhelm Brandes, Stefan Dutzmann
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Patent number: 5001144Abstract: Disclosed are novel 3-hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors useful as antihypercholesterolemic agents represented by the formula ##STR1## and the corresponding ring-opened hydroxy acids derived therefrom and pharmaceutically acceptable salts thereof.Phamaceutical compositions containing said compounds and method of inhibiting the biosynthesis of cholesterol therewith are also disclosed.Type: GrantFiled: April 17, 1990Date of Patent: March 19, 1991Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.Inventors: John R. Regan, Kent W. Neuenschwander
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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: 4971981Abstract: Novel substituted 1,3-dioxolan and 1,4-dioxan derivatives of formula I ##STR1## in which R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 each independently of the others represents hydrogen or C.sub.1 -C.sub.4 -alkyl or, if n=1,R.sub.2 and R.sub.4 together represent one of the radicals ##STR2## R.sub.7 represents hydrogen, halogen, methyl, ethyl, C.sub.1 -C.sub.2 -alkyl substituted by 1 to 5 halogen atoms, methoxy, ethoxy or C.sub.1 -C.sub.2 -alkoxy substituted by 1 to 5 halogen atoms;R.sub.8 represents a halogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -alkyl substituted by 1 to 7 halogen atoms, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.3 -alkoxy substituted by 1 to 7 halogen atoms, or cyano;U represents a grouping --CH.dbd. or --N.dbd.;X represents --O--, --S-- or --N(R.sub.9)--;Y represents --O--, --S--, --S(O)--, --S(O.sub.2)--, --CH.sub.2 --, --CO-- or --N(R.sub.9)--, whereinR.sub.9 represents hydrogen, C.sub.1 -C.sub.Type: GrantFiled: January 19, 1988Date of Patent: November 20, 1990Assignee: Ciba-Geigy CorporationInventor: Friedrich Karrer
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Patent number: 4929613Abstract: The novel series of quinoline-, naphthyridine- and benzoxazine-carboxylic acids useful as antibacterial agents is described. Novel methods for preparing the compounds as well as novel intermediates are also described as are methods for their formulation and the use thereof in treating bacterial infections.Type: GrantFiled: July 25, 1988Date of Patent: May 29, 1990Assignee: Warner-Lambert CompanyInventors: Townley P. Culbertson, John M. Domagala, Susan E. Hagen, Joseph P. Sanchez
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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: 4870098Abstract: This invention encompasses compounds of Formula I ##STR1## and the pharmaceutically acceptable salts and geometrical and optical isomers thereof wherein:Alk is alkylene or hydroxyalkylene containing 1-6 carbon atoms;Ar is 5,6,7,8-tetrahydro-1-naphthalenyl or phenyl optionally substituted with one or more substituents selected from lower alkyl containing 1 to 6 carbon atoms, hydroxy, lower alkoxy containing 1 to 6 carbon atoms, or lower alkanoyl containing 1 to 6 carbon atoms;R is hydrogen and lower alkyl containing 1 to 6 carbon atoms;X, Y, and Z are each independently O or S with S optionally oxidized to S.dbd.O;m is an integer from 0 to 3;n is an integer from 0 to 5.The compounds are useful as anti-allergy agents and anti-inflammatory agents.Type: GrantFiled: January 17, 1989Date of Patent: September 26, 1989Assignee: G. D. Searle & Co.Inventors: Michael A. Stealey, Richard M. Weier
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Patent number: RE41366Abstract: The invention relates to a method for the synthesis of galanthamine, the derivatives and analogues thereof of formula (1) where R1=a hydrogen atom, R2=a hydroxy group, R1 and R2 together form ?O, R3, R4, and R5 independently=a hydrogen atom, a hydroxy group or a (C1-C2)alkoxy group, R6?H, (C1-C12)alkyl, (CH2)nNR7R8, or —(CH2)nN+R7R8R9 where n=1 to 12, Z=two hydrogen atoms, or an oxygen atom and X=an oxygen, sulphur or nitrogen atom, or a —SO, —SO2, or —NR6 group where R6 is as defined above or is an amine protecting group.Type: GrantFiled: June 14, 2002Date of Patent: June 1, 2010Assignee: Centre National del la Recherche Scientifique (CNRS)Inventors: Claude Thal, Catherine Guillou, Jean-Luc Beunard, Emmanuel Gras, Pierre Potier