Multiple Bond Between Two Acyclic Carbons Patents (Class 558/217)
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Patent number: 8765988Abstract: The invention relates to a novel important lycopene intermediate 3,7,11-trimethyl-1,3,6,10-tetraene-dodecyl diethyl phosphonate. A current lycopene intermediate 2,4,6,10-tetra-double bond pentadec-carbon phosphonate is difficult to synthesize. The invention provides a novel intermediate, which has the following synthesis steps of: preparing 2,6,10-trimethyl-3,5,9-undecane triene-1-aldehyde from pseudoionone; preparing 2,6,10-trimethyl-2,5,9-undecane triene-1-aldehyde from the 2,6,10-trimethyl-3,5,9-undecane triene-1-aldehyde; and subjecting the 2,6,10-trimethyl-2,5,9-undecane triene-1-aldehyde and tetraethyl methylenediphosphonate to condensation reaction to obtain target product. The invention can generate novel intermediate from raw material pseudoionone only by four reactions, thus the reactions are easy to control and great industrial value are achieved.Type: GrantFiled: March 9, 2011Date of Patent: July 1, 2014Inventors: Xuejun Lao, Runpu Shen, Weidong Ye, Xiaohua Song, Luo Liu, Chunlei Wu, Yibin Wu, Liujiang Hu
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Publication number: 20130066098Abstract: The present invention provides phosphonate compounds and methods of preparing the phosphonate compounds so as to allow, for example, increased capability to modify nanoparticles for targeted drug delivery applications.Type: ApplicationFiled: August 30, 2012Publication date: March 14, 2013Applicant: Mallinckrodt LLCInventors: Thomas E. Rogers, Kah Tiong Kuan
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Publication number: 20120330048Abstract: The invention relates to a novel important lycopene intermediate 3,7, 11-trimethyl-1,3,6,10-tetraene-dodecyl diethyl phosphonate. A current lycopene intermediate 2,4,6,10-tetra-double bond pentadec-carbon phosphonate is difficult to synthesize. The invention provides a novel intermediate, which has the following synthesis steps of: preparing 2,6,10-trimethyl-3,5,9-undecane triene-1-aldehyde from pseudoionone; preparing 2,6,10-trimethyl-2,5,9-undecane triene-1-aldehyde from the 2,6,10-trimethyl-3, 5,9-undecane triene-1-aldehyde; and subjecting the 2,6,10-trimethyl-2,5,9-undecane triene-1-aldehyde and tetraethyl methylenediphosphonate to condensation reaction to obtain target product. The invention can generate novel intermediate from raw material pseudoionone only by four reactions, thus the reactions are easy to control and great industrial value are achieved.Type: ApplicationFiled: March 9, 2011Publication date: December 27, 2012Applicants: UNIVERSITY OF SHAOXING, ZHEJIANG MEDICINE CO., LTD. XINCHANG PHARMACEUTICAL FACTORYInventors: Xuejun Lao, Runpu Shen, Weidong Ye, Xiaohua Song, Luo Liu, Chunlei Wu, Yibin Wu, Liujiang Hu
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Publication number: 20100204184Abstract: The invention concerns novel phosphonate derivatives, preparation method, use thereof as ligands modulating T ?9?2 lymphocyte activity and pharmaceutical compositions comprising them.Type: ApplicationFiled: January 14, 2010Publication date: August 12, 2010Applicants: LABORATOIRES MAYOLY SPINDLER, CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE, UNIVERSITE MONTPELLIER IIInventors: Jean-Louis Montero, Ibrahim Zgani, Chantal Menut, Valérie Gallois
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Patent number: 6215013Abstract: A method for the preparation of alkene phosphonic acids and salts thereof, such as VDPA (vinylidene diphosphonic acid) is disclosed. The products can be produced in a stable, substantially pure form and in high yield. The method includes the azeotropic removal of water from salts of &agr;-hydroxy-alkane diphosphonic acid dimer or corresponding acids thereof, and the pyrolysis of the dehydrated reactant at a temperature of from 170° C. to 300° C. There may be included a step to convert anhydrides which have been formed during the pyrolysis. The method may include the use of heat transfer agents and/or bases, and may be carried out at elevated or reduced pressure.Type: GrantFiled: September 5, 2000Date of Patent: April 10, 2001Assignee: Rhodia Consumer Specialties LimitedInventors: Gary Woodward, Timothy Kevin Brierley, Ranbir Singh Padda, John Christopher Harris, Aidan Michael Hayes
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Patent number: 6111127Abstract: A process for the preparation of an unsaturated phosphonic acid ester of the formula:R.sup.1 CH.dbd.C(R.sup.2)P(.dbd.O)(OR.sup.3).sub.2wherein an acetylene compound of the formula:R.sup.1 C.tbd.CR.sup.2is reacted with a secondary phosphite of the formula:HP(.dbd.O)(OR.sup.3).sub.2in the presence of a palladium complex catalyst. The process is characterized in that the reaction is performed in the presence of water or in that the palladium complex catalyst contains, as a ligand, a 1,3-bisphosphinopropane of the formula: ##STR1## wherein R.sup.4, R.sup.5, R.sup.6 and R.sup.7 stand, independently from each other, for an alkyl group, a cycloalkyl group, an aralkyl group or an aryl group.Type: GrantFiled: September 13, 1999Date of Patent: August 29, 2000Assignees: Agency of Industrial Science & Technology, Masato TanakaInventors: Masato Tanaka, Li-Biao Han
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Patent number: 5973179Abstract: The present invention describes novel phosphonate reagent compositions of the formula: ##STR1## wherein R and R'=C.sub.1 -C.sub.4 alkyl groups, or R, R'=(CH.sub.2).sub.n (n=2 or 3) or [CH.sub.2 C(CH.sub.3).sub.2 CH.sub.2 ].The invention also describes allylic C-15 phosphonate compounds of the formula: ##STR2## wherein R and R'=C.sub.1 -C.sub.4 alkyl groups. The invention also describes methods of preparing phosphonate reagent compositions (4), allylic phosphonate compounds (5), and lycopene.Type: GrantFiled: November 19, 1998Date of Patent: October 26, 1999Assignee: Loyola University of ChicagoInventors: James H. Babler, Harvey W. Posvic
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Patent number: 5847185Abstract: Allenic phosphonate reagent compositions are described which have the formula: ##STR1## wherein R and R'=C.sub.1 -C.sub.4 alkyl groups, or R, R'=(CH.sub.2).sub.n (n=2 or 3) or ?CH.sub.2 C(CH.sub.3).sub.2 CH.sub.2 !.Also described are methods for forming such allenic phosphonates from ethynyl-.beta.-ionol, and for converting these allenic compounds to allylic phosphonate compounds which can be used in the synthesis of a variety of biologically-active materials.Type: GrantFiled: November 21, 1997Date of Patent: December 8, 1998Assignee: Loyola University of ChicageInventor: James H. Babler
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Patent number: 5574025Abstract: The compounds disclosed inhibit the prenylation of several proteins. These compounds are potent inhibitors of famesyl-protein transferase and geranylgeranyl-protein transferase. Further contained in this invention are chemotherapeutic compositions containing these prenyl-transferase inhibitors and methods for their production.Type: GrantFiled: October 26, 1994Date of Patent: November 12, 1996Assignee: Merck & Co., Inc.Inventors: Neville J. Anthony, Robert P. Gomez, Charles A. Omer
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Patent number: 5532226Abstract: Novel benzylphosphonate compounds of the general formula I: ##STR1## are disclosed as useful in treating bone wasting diseases including postmenopausal osteoporosis in increasing in mammals bone formation and bone mass.Type: GrantFiled: December 9, 1993Date of Patent: July 2, 1996Assignee: Ortho Pharmaceutical CorporationInventors: Keith Demarest, Charles Schwender, David Wustrow
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Patent number: 5475128Abstract: Process for the continuous preparation of dialkyl vinylphosphonates using catalysts at temperatures of from 150.degree. to 270.degree. C. by dissociation of dialkyl acetoxyethanephosphonates at a pressure of from 5 to 500 mbar in contact with a liquid, catalytically active medium while drawing off the dialkyl vinylphosphonates formed and other volatile reaction products as vapors, by conveying the liquid medium in forced circulation via an evaporator while feeding in fresh dialkyl acetoxyethanephosphonate, if desired admixed with catalyst, corresponding to the distillation of dialkyl vinylphosphonates and other volatile compounds, and drawing off non-volatile material formed as byproduct from the liquid circuit to maintain constant conditions.Type: GrantFiled: December 12, 1994Date of Patent: December 12, 1995Assignee: Hoechst AktiengesellschaftInventors: Gunter Roscher, Wolf-Dietmar Kaufmann, Bernd Laugwitz
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Patent number: 5424478Abstract: The present specification relates to an industrially advantageous process for producing vitamin A derivatives which are useful as medicaments, feed additives, food additives and the like. The process provides vitamin A derivatives, particularly all-trans vitamin A derivatives in high yield and purity.Type: GrantFiled: March 22, 1994Date of Patent: June 13, 1995Assignee: Takeda Chemical Industries, Ltd.Inventors: Mitsutaka Tanaka, Tadashi Hanaoka, Kunio Takanohashi
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Patent number: 5352822Abstract: The present invention discloses pesticidally active compounds of formula (II) ##STR1## or a salt thereof, wherein Q is an monocyclic aromatic ring, or fused bicyclic ring system of which at least one ring is aromatic containing 9 or 10 atoms of which one may be nitrogen and the rest carbon each ring system being optionally substituted, or Q is a dihalovinyl group or a group R.sup.6 --C.tbd.C-- where R.sup.6 is C.sub.1-4 alkyl, tri C.sub.1-4 alkylsilyl, halogen or hydrogen; R.sup.2, R.sup.3 , R.sup.4 and R.sup.5 are the same or different with at least one being hydrogen and the others being independently selected from hydrogen, halo, C.sub.1-4 alkyl or C.sub.1-4 haloalkyl; and R.sup.1 is selected from hydrogen and C.sub.1-8 hydrocarbyl optionally substituted by dioxalanyl, halo, cyano, trifluoromethyl, trifluoromethylthio or C.sub.1-6 alkoxy and X.sup.1 is hydrogen, fluoro or chloro.Type: GrantFiled: April 7, 1993Date of Patent: October 4, 1994Assignee: Roussel UclafInventors: Robert J. Blade, George S. Cockerill, John E. Robinson
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Patent number: 5177238Abstract: An improved process for the production of allylphosphonic acid dialkyl esters in high yield and selectivity by the gradual addition of trialkyl phosphite to react with the appropriate allyl halide in the presence of a divalent nickel catalyst and, optionally, a polymerization inhibiting compound, e.g. hydroquinone.Type: GrantFiled: July 16, 1991Date of Patent: January 5, 1993Assignee: W. R. Grace & Co.-Conn.Inventors: Charles G. Carter, David R. Sterrenburg
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Patent number: 5166198Abstract: A compound of formula (I), or a pharmaceutically acceptable salt thereof: ##STR1## wherein R.sub.1 is hydroxy or amino;R.sub.2 is hydrogen or amino;R.sub.3 is hydrogen, hydroxymethyl or acyloxymethyl;R.sub.4 is hydrogen or (when R.sub.3 =H and Z is a bond or CH.sub.2) hydroxy, acyloxy, hydroxymethyl or acyloxymethyl;Z is a bond, or a group CHR.sub.8 wherein R.sub.8 is hydrogen, or (when R.sub.3 =R.sub.4 =H), R.sub.8 is hydroxy, acyloxy, hydroxymethyl or acyloxymethyl;R.sub.5 is a group of formula: ##STR2## wherein R.sub.6 and R.sub.7 are independently selected from hydrogen,C.sub.1-6 alkyl and optionally substituted phenyl.Type: GrantFiled: March 28, 1990Date of Patent: November 24, 1992Assignee: Beecham p.l.c.Inventors: Michael R. Harnden, David M. Duckworth, Halina T. Serafinowska
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Patent number: 5142084Abstract: A novel process for rearranging triallyl phosphite to diallyl allylphosphonate ester is disclosed. The process involves heating triallyl phosphite in the presence of a soluble, inorganic bromide or iodide catalyst. The rearrangement process is useful in a 3-step process for the preparation allylphosphonic acid from trialkyl phosphite without the isolation of intermediates.Type: GrantFiled: October 11, 1991Date of Patent: August 25, 1992Inventors: Charles G. Carter, David R. Sterrenburg
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Patent number: 5132444Abstract: A process for the preparation of vinyl phosphonic derivatives of the general formula I ##STR1## in which R.sup.1 and R.sup.2 are the same or different and may stand for hydrogen or a C.sub.1 -C.sub.8 -alkyl, a C.sub.6 -C.sub.10 -aryl, or a C.sub.8 -C.sub.10 -aralkyl radical optionally substituted by Cl or Br, and in which R.sup.1 and R.sup.2 may alternatively be joined together to form an alicyclic ring having from 3 to 12 carbon atoms in the ring, wherein an ethane phosphonic ester of the general formula II ##STR2## in which R.sup.3 and R.sup.4 have the meanings stated above for R.sup.1 and R.sup.2 except for hydrogen and X denotes a hydroxy group, a halogen atom, or a radical of the formula--OR.sup.5,in which R.sup.5 is a hydrogen atom or a radical of the formula ##STR3## in which R.sup.6 is a C.sub.1 -C.sub.6 -alkyl radical or an alicyclic ring, is converted in the gas phase in the presence of a solid catalyst.Type: GrantFiled: April 22, 1991Date of Patent: July 21, 1992Assignee: BASF AktiengesellschaftInventors: Andreas Northemann, Martin Fischer, Ludwig Wambach
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Patent number: 5128333Abstract: Compounds of the general formula I ##STR1## wherein R1 represents --R3, --OR3 or --N(R3).sub.2, in which R3 is alkyl of 1 to about 18 carbon atoms;R2 represents alkyl of 1 to about 18 carbon atoms; andX represents --OR3, halogen, --CN, --SR4 or --N(R4).sub.2, in which R4 is alkyl of 1 to about 5 carbon atoms,with the proviso that at least one of R2 and R3 is a pheromone alkyl chain.Members of this class of compounds have been shown to exhibit outstanding activity in disrupting pheromone-mediated behavior of various insects, in particular moths.Type: GrantFiled: August 15, 1991Date of Patent: July 7, 1992Assignee: Regents of the University of CaliforniaInventors: T. Roy Fukuto, Richard S. Vetter, Thomas C. Baker, Mangel S. Malik
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Patent number: 5061819Abstract: Processes for synthesizing novel phosphonate diester compounds of the general formula ##STR1## are disclosed and claimed. The claimed process includes forming a reaction mixture of a C-14 aldehyde and a methylene-bis-phosphonic acid ester, separating a pentadienyl phosphonic acid dialkyl ester intermediate from the reaction mixture, optionally isomerizing the intermediate in the presence of a basic catalyst, and isolating the desired pentadienylphosphonic acid dialkyl ester compound. The isolated phosphonate compounds made according to the processes of the present invention may be employed in synthesizing retinoids such as retinoic acid or carotenoids such as beta-carotene.Type: GrantFiled: February 5, 1990Date of Patent: October 29, 1991Assignee: Loyola University of ChicagoInventor: James H. Babler
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Patent number: 5047578Abstract: Novel phosphonic acid-containing compounds such as (2-(4-ethenylphenyl)ethenyl)-phosphonic acid and esters thereof are disclosed. A method of preparation of the phosphonic acids comprising contacting a diethylenically unsaturated aromatic compound and phosphorus pentachloride in the presence of sulfur dioxide is also disclosed.The compounds of this invention are useful as monomers for the preparation of polymers having enhanced anti-corrosive properties.Type: GrantFiled: April 20, 1988Date of Patent: September 10, 1991Assignee: The Dow Chemical CompanyInventors: Gerald K. McEwen, Donald L. Schmidt
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Patent number: 4916250Abstract: Novel phosphonate compounds of the formula ##STR1## are disclosed and claimed, as well as methods for manufacturing the phosphonates from C-14 through C-16 aldehydes. The phosphonate compounds of the present invention can be employed to form 13-cis retinoic acid, retin-A and beta-carotene.Type: GrantFiled: October 31, 1988Date of Patent: April 10, 1990Assignee: Loyola University of ChicagoInventor: James H. Babler
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Patent number: 4758384Abstract: Novel phosphonic acid-containing compounds such as (2-(4-ethenylphenyl)ethenyl)-phosphonic acid and esters thereof are disclosed. A method of preparation of the phosphonic acids comprising contacting a diethylenically unsaturated aromatic compound and phosphorus pentachloride in the presence of sulfur dioxide is also disclosed.The compounds of this invention are useful as monomers for the preparation of polymers having enhanced anti-corrosive properties.Type: GrantFiled: August 7, 1987Date of Patent: July 19, 1988Assignee: The Dow Chemical CompanyInventors: Gerald K. McEwen, Donald L. Schmidt
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Patent number: 4659702Abstract: Compounds and compositions containing them, for insecticidal control, particularly for use as soil and/or foliar insecticides, have the formula ##STR1## in which R.sub.1 is C.sub.1 -C.sub.3 alkyl;R.sub.2 is C.sub.1 -C.sub.6 alkyl, or C.sub.5 -C.sub.6 cycloalkyl;R.sub.3 is hydrogen or C.sub.1 -C.sub.3 alkyl;R.sub.4 is hydrogen, C.sub.1 -C.sub.4 alkyl, phenyl, halogen, or halo-(C.sub.1 -C.sub.4 alkyl);R.sub.5 and R.sub.6 are independently hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, phenyl, or C.sub.2 -C.sub.5 carboalkoxy; orR.sub.3 and R.sub.5 taken together form a trimethylene group; provided that if R.sub.3, R.sub.5 and R.sub.6 are all hydrogen, R.sub.4 is other than hydrogen.Type: GrantFiled: February 15, 1985Date of Patent: April 21, 1987Assignee: Stauffer Chemical CompanyInventors: Charles G. Chavdarian, Valerie F. Heusinkveld
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Patent number: 4659703Abstract: Insecticides have the formula ##STR1## in which R.sub.1 methyl or ethyl and R.sub.2 is C.sub.3 -C.sub.5 alkyl.Type: GrantFiled: December 16, 1985Date of Patent: April 21, 1987Assignee: Stauffer Chemical CompanyInventor: Charles G. Chavdarian
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Patent number: 4654430Abstract: Compounds having the formula ##STR1## in which R.sub.1 is methyl or ethyl and R.sub.2 is ethyl or a C.sub.3 -C.sub.5 branched alkyl group other than, 1,2-dimethylpropyl, are effective soil insecticides.Type: GrantFiled: May 27, 1986Date of Patent: March 31, 1987Assignee: Stauffer Chemical CompanyInventor: Alexandra B. Shortt
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Patent number: 4614735Abstract: Compounds having the formula ##STR1## in which R.sub.1 is methyl or ethyl and R.sub.2 is ethyl or a C.sub.3 -C.sub.5 branched alkyl group other than 1,2-dimethylpropyl, are effective soil insecticides.Type: GrantFiled: December 24, 1984Date of Patent: September 30, 1986Assignee: Stauffer Chemical CompanyInventor: Alexandra B. Shortt
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Patent number: 4608207Abstract: Dialkyl vinylphosphonates are prepared by heating the new dialkyl 2-alkylcarbonatoethanephosphonates in the presence of catalysts. Also disclosed is a process for making the new dialkyl 2-alkylcarbonatoethanephosphonate by transesterification of a dialkyl 2-carboxyethanephosphonate with a dialkyl carbonate in the presence of a transesterification catalyst.Type: GrantFiled: May 4, 1984Date of Patent: August 26, 1986Assignee: Bayer AktiengesellschaftInventors: Hans-Josef Buysch, Peter Mues
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Patent number: 4595783Abstract: The invention relates to intermediate compounds having the general formula I ##STR1## in which R.sup.1 is H, an alkyl, arylalkyl or an aliphatic acyl radical, preferably a benzyl or acetyl group and wherein X and Y together span an additional bond between the X and Y carrying C atoms (Ia) or in which Y is OH and X is H (Ib) and in which the dotted line can represent an additional bond particularly[2R,1'Z,3'E,7'E]-6-benzyloxy-2,5,7,8-tetramethyl-2-(4',8',12'-trimethyl-tri deca-1',3',7'-trien-1'-yl)chroman and6-benzyloxy-2,5,7,8-tetramethyl-2-(1'-hydroxy-4',8',12'-trimethyl-trideca-3 ',7'-diene-1'-yl)chroman, as well as compounds and methods of preparing compounds having the general formula II ##STR2## in which Z is one of the groups ##STR3## wherein R.sup.2 is an alkyl group with 1 to 4 carbon atoms preferably CH.sub.3 or C.sub.2 H.sub.Type: GrantFiled: August 31, 1984Date of Patent: June 17, 1986Inventors: Friedrich Vogel, Joachim Paust, Axel Nuerrenbach
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Patent number: 4582652Abstract: Allyl phosphonate diesters are converted to vinyl phosphonate diesters by isomerization with a catalytically effective amount of one or more metal hydroxide catalysts.Type: GrantFiled: July 2, 1984Date of Patent: April 15, 1986Assignee: Allied CorporationInventors: David Nalewajek, David S. Soriano