Abstract: A modified alkali metal or ammonium huminate being made from molecules of the group consisting of ##STR1## wherein R.sub.1, R.sub.3 and R.sub.4 are individually hydrogen or --OH, R.sub.2 is ##STR2## or --CH.sub.2 -- and R.sub.5 and R.sub.6 are individually selected from the group consisting of hydrogen, --OH and --OCH.sub.3, with the proviso that R.sub.4, R.sub.5 and R.sub.6 are not all hydrogen at the same time and their preparation and their medical uses.
Abstract: The present invention relates to labelled resiniferatoxin and congeners thereof. Preferably, the labelled compounds of the invention are radio or fluorescently labelled. The invention is further directed to compositions comprising these labelled compounds, as well as to methods of using these compounds.
Type:
Grant
Filed:
June 29, 1990
Date of Patent:
August 3, 1993
Assignee:
The United States of America as represented by the Department of Health and Human Services
Inventors:
Peter M. Blumberg, Arpad Szallasi, Zoltan Szallasi
Abstract: A process for synthesizing polyoxa tetracyclics which involves the ozonolysis of a single-ring-structure vinyl silane with resulting direct formation of the desired multiple ring material. The polyoxa tetracyclic compounds have the formula ##STR1## The vinyl silanes have the structure ##STR2## The vinyl silanes are new chemical compounds as are corresponding primary ozonide and dioxetane intermediates. In a preferred embodiment, this invention provides a total synthesis of the antimalarial artemisinin.
Type:
Grant
Filed:
July 18, 1990
Date of Patent:
July 6, 1993
Assignee:
SRI International
Inventors:
Mitchell A. Avery, Clive Jennings-White
Abstract: This invention is a new method for preparing compounds useful as antimalarial agents having the formula; ##STR1## wherein R is hydrogen, a linear, branched or cyclo lower alkyl group having 1 to 8 carbon atoms; aminoalkyl; branched aminoalkyl; hydroxyalkyl: alkylcarboxylate or alkylbenzoate groups having 1 to 5 carbon atoms in the alkyl chains; aryl; alkoxy-substituted aryl; heteroaryl; and pyridinium groups. The method comprises treating artemisinic acid with a methylating agent followed by a stereoselective reduction of the methylated compound, subjecting the reduced compound to a Grignard addition followed by chiral photoxidation with subsequent treatment with a cyclization agent.
Abstract: 10-substituted ether derivatives of 3.alpha., 12.alpha.-Epoxy-3,4,5 5a.alpha., 6,7,8,8a.alpha.,9,10,12.beta., 12a-dodecahydro-10-hydroxy-3.beta.,6.alpha.,9.beta.-trimethylpyano-(4,3-j) (1,2) benzodioxepin, also known as Dihydroartemisinin or Dihydroquinghaosu (DHQ), pharmaceutically acceptable salts thereof, processes for their preparation and their use as chemotherapeutics against protozoal infections are provided.
Type:
Grant
Filed:
November 27, 1991
Date of Patent:
July 6, 1993
Assignee:
Hoechst Aktiengesellschaft
Inventors:
Bindumadhavan Venugopalan, Chintamani P. Bapat, Pravin J. Karnik, Bansi Lal, Dipak K. Chatterjee, Subramani N. Iver, Richard H. Rupp
Abstract: Dyes of the formula ##STR1## in which F is the radical of an indigoid dye, of a benzothioxanthene or of an aromatic dye which contains at least 4 alicyclic and/or heterocyclic, fused six-membered rings and at least two ring keto groups and is not water-soluble, R.sub.1 is a substituted or unsubstituted C.sub.1-4 -alkyl radical, a substituted or unsubstituted cycloalkyl radical, a substituted or unsubstituted aryl radical or a radical of the formula--A--Qwhere A is a substituted or unsubstituted C.sub.1-4 -alkylene radical and Q is a basic radical, which may be quaternised, and R.sub.2 is hydrogen or a substituted or unsubstituted C.sub.1-4 -alkyl radical, or in which R.sub.1 and R.sub.2 together with the ##STR2## group are a phthalimide radical, and R.sub.3 is hydrogen, a substituted or unsubstituted C.sub.1-4 -alkyl radical, a substituted or unsubstituted aryl radical, a C.sub.1-4 -alkoxycarbonyl radical or a N,N-di-C.sub.1-4 -alkylcarboxamide radical and n is 1, 2, 3 or 4.
Abstract: Non-sulphurized overbased metal salts of sulphur-free calixarenes having a substituent hydroxyl group or groups available for reaction with metal base and their preparation are claimed. The salts are useful as additives to lubricating oils by reason of their acids neutralization capability, their detergent and their antioxidant properties.
Type:
Grant
Filed:
February 6, 1992
Date of Patent:
April 27, 1993
Assignee:
BP Chemicals (Additives) Limited
Inventors:
Stephen J. Cook, Sean P. O'Conner, Andrew Pearce
Abstract: A process for synthesizing oxygen-containing polyoxatetracycle compounds and in particular analogs of the antimalarial agent known as qinghaosu or artemisinin is disclosed. The process employs as a reactant an olefinically unsaturated bicyclic bridging ketone having nonenolizable bridgehead moieties for both of its alpha positions. This ketone is converted to a vinylsilane that is subjected to ozonolytic cleavage of its olefinic bond to yield a member of a family of unique carboxyl/carbonyl-substituted vinylsilanes which may in turn optionally be subjected to a wide range of reactions prior to a final ozonolysis/acidification step which closes the oxygen-containing ring structure. The various intermediates are claimed as aspects of this invention as are novel tetracycles and their use as antimalarials.
Abstract: The present invention resides in the discovery of a new class of compounds defined herein as "chromogenic hemispherands" useful for the measurement of ions, in particular, ions in aqueous solution, which have the structure ##STR1## wherein: R, same or different, is hydrogen, lower alkyl, lower alkylidene, lower alkenyl, allyl or aryl;R', same or different, is lower alkyl, lower alkylidene, lower alkenyl, allyl or aryl;R", same or different, is hydrogen, lower alkyl, lower alkylidene, lower alkenyl, allyl or aryl;Q is a chromogenic moiety capable of providing the appearance of or change in color, or which is otherwise capable of providing a detectable response in the presence of a particular cation;m is 1 to about 3;n is 0 to about 3;A is an aliphatic or aromatic subunit, e.g.
Type:
Grant
Filed:
August 8, 1990
Date of Patent:
January 5, 1993
Assignees:
Miles Inc., The Regents of the University of California
Inventors:
Donald J. Cram, Eddy Chapoteau, Bronislaw P. Czech, Carl R. Gebauer, Roger C. Helgeson, Anand Kumar, Koon-Wah Leong
Abstract: The fungus Beauveria sulfurescens has been employed to introduce hydroxyl groups into artemisinin and derivatives of artemisinin, an antimalarial. Hydroxylated derivatives of artemisinin and derivatives of artemisinin produced thereby possess antimalarial activity, and can serve as intermediates in the synthesis of further derivatives useful in treating malaria.
Type:
Grant
Filed:
October 31, 1991
Date of Patent:
December 15, 1992
Assignee:
The United States of America as represented by the Secretary of the Department of Health and Human Services
Abstract: The invention concerns novel pharmaceutical compositions for use in the treatment of certain complications of diabetes and galactosemia and which contain a nitromethane derivative (or its non-toxic salt) as active ingredient. The nitromethane derivatives are inhibitors of the enzyme aldose reductase. Many of the inhibitors are novel and are provided, together with processes for their manufacture and use, as further features of the invention.
Type:
Grant
Filed:
February 6, 1989
Date of Patent:
October 6, 1992
Assignee:
Imperial Chemical Industries PLC
Inventors:
Steven P. Brown, Anthony L. Cooper, Jethro L. Longridge, Jeffrey J. Morris, John Preston
Abstract: Novel fluorogenic ionophores have been synthesized which selectively bind ions such as potassium and sodium, even in neutral aqueous and alcoholic media and respond to such binding by fluorescence quenching or enhancement. These ionophores are ideal for the selective and direct determination of ions in biological or environmental samples and the like. The ionophores are also suitable for incorporation into fiber optic-based sensors for the continuous in vivo or in vitro monitoring of metal ions in blood or other biological fluids.
Type:
Grant
Filed:
August 24, 1987
Date of Patent:
August 4, 1992
Assignee:
Allied-Signal Inc.
Inventors:
Divakaran Masilamani, Mariann E. Lucas, George S. Hammond
Abstract: Non-sulphurized overbased metal salts of sulphur-free calixarenes having a substituent hydroxyl group or groups available for reaction with metal base are claimed. The salts are useful as additives to lubricating oils by reason of their acids neutralization capability, their detergent and their antioxidant properties.
Type:
Grant
Filed:
March 22, 1991
Date of Patent:
May 19, 1992
Assignee:
BP Chemicals (Additive) Limited
Inventors:
Stephen J. Cook, Sean P. O'Connor, Andrew Pearce
Abstract: A novel series of polycyclic amines, derivatives, methods of making the compounds, novel intermediates, compositions containing them, and methods for using them in the treatment and prevention of cerebrovascular disorders are disclosed.
Type:
Grant
Filed:
February 27, 1990
Date of Patent:
December 10, 1991
Inventors:
Christopher F. Bigge, Sheryl J. Hays, Graham Johnson, Perry M. Novak, Daniel F. Ortwine
Abstract: The application describes nitrogen-containing an oxacalixarene or calixarene derivative of formula I: ##STR1## wherein m'+m"=0-8n=0-8m'.gtoreq.1/2(m'+M")3.ltoreq.m'+m"+n.ltoreq.8if n=0, m'+m".gtoreq.4R.sup.3 is H, halogen, or hydrocarbyl, aryl, hydrocarbylaryl or a substituted derivative thereof and R.sup.3 may be the same or different on each aryl group;R.sup.1 and R.sup.15 which may be the same or different are H or hydrocarbyl, aryl, hydrocarbylaryl or a substituted derivative thereof;R.sup.2 is selected from:R.sup.4 which is H, or hydrocarbyl, aryl, hydrocarbylaryl or a substituted derivative thereof, ##STR2## wherein R.sup.5 and R.sup.6 which may be the same or different are H, or hydrocarbyl, aryl, hydrocarbylaryl, or a substituted derivative thereof,-OR.sup.1, wherein R.sup.1 is as defined aboveand R.sup.17 which is a residue of a hydrocarbyl, aryl, or hydrocarbylaryl group or of a substituted derivative thereof providing a bond to another oxacalixarene or calixarene derivative of formula I wherein R.
Type:
Grant
Filed:
September 23, 1988
Date of Patent:
August 27, 1991
Assignee:
Loctite (Ireland) Ltd.
Inventors:
Stephen J. Harris, Maureen G. MacManus, John Guthrie
Abstract: This invention provides a new antimalarial compound, deoxoartemisinin, having the formula: ##STR1## Antimalarial compositions consisting essentially of the compound in admixture with a non-toxic, pharmaceutically-acceptable carrier. A method for treating malaria comprising administering a therapeutically effective concentration of the compound, preferably in admixture with a non-toxic, pharmaceutically-acceptable carrier. A method of preparing the deoxoartemisinin.
Abstract: A process for synthesizing oxygen-containing polyoxatetracycle compounds and in particular analogs of the antimalarial agent known as qinghaosu or artemisinin is disclosed. The process employs as a reactant an olefinically unsaturated bicyclic bridging ketone having nonenolizable bridgehead moieties for both of its alpha positions. This ketone is converted to a vinylsilane that is subjected to ozonolytic cleavage of its olefinic bond to yield a member of a family of unique carboxyl/carbonyl-substituted vinylsilanes which may in turn optionally be subjected to a wide range of reactions prior to a final ozonolysis/acidification step which closes the oxygen-containing ring structure. The various intermediates are claimed as aspects of this invention as are novel tetracycles and their use as antimalarials.
Abstract: A process for the epimerization of .alpha.- to .beta.-ethyletherartemisininelactol (arteether) or preparation of arteether, useful in the treatment of malaria, from artemisininelactol, comprises reacting starting material in a solvent including an acid catalyst, the reaction of artemisininelactol also including an etherifying ethyl moiety, and isolating the product.
Abstract: A process for synthesizing polyoxa tetracyclics which involves the ozonolysis of a single-ring-structure vinyl silane with resulting direct formation of the desired multiple ring matrial. The polyoxa tetracyclic compounds have the formula ##STR1## The vinyl silanes have the structure ##STR2## The vinyl silanes are new chemical compounds as are corresponding primary ozonide and dioxetane intermediates. In a preferred embodiment, this invention provides a total synthesis of the antimalarial artemisinin.
Type:
Grant
Filed:
February 15, 1989
Date of Patent:
October 16, 1990
Assignee:
SRI International
Inventors:
Mitchell A. Avery, Clive Jennings-White
Abstract: Oxacalixarenes of general formula I: ##STR1## wherein m=0-7 and n=1-8 with the proviso that m+n.ltoreq.8;R is hydrogen, halogen, or hydrocarbyl, aryl, hydrocarbylaryl or a substituted derivative thereof, and R may be the same or different on each aryl group; andR' is hydrocarbyl, aryl, hydrocarbylaryl, hydrocarbyloxy, aryloxy or hydrocarbylaryloxy or a substituted derivative thereof.The invention also provides a method of preparing oxacalixarenes of formula I, and cyanoacrylate adhesive compositions including as accelerator an oxacalixarene of formula I.
Abstract: This invention provides a new antimalarial compound, deoxoartemisinin, having the formula: ##STR1## Antimalarial compositions consisting essentially of the compound in admixture with a non-toxic, pharmaceutically-acceptable carrier. A method for treating malaria comprising administering a therapeutically effective concentration of the compound, preferably in admixture with a non-toxic, pharamceutically-acceptable carrier. A method of preparing the doxoartemisinin.
Abstract: Oxacalixarenes of general formula I: ##STR1## wherein m=0-7 and n=1-8 with the proviso that m+n.ltoreq.8;R is hydrogen, halogen, or hydrocarbyl, aryl, hydrocarbylaryl or a substituted derivative thereof, and R may be the same or different on each aryl group; andR' is hydrocarbyl, aryl, hydrocarbylaryl, hydrocarbyloxy, aryloxy or hydrocarbylaryloxy or a substituted derivative thereof.The invention also provides a method of preparing oxacalixarenes of formula I, and cyanoacrylate adhesive compositions including as accelerator an oxacalixarene of formula I.
Abstract: Retinoid-like activity is exhibited by compounds of the formula ##STR1## where X is S, O or NR.sub.1 where R.sub.1 is hydrogen or lower alkyl; n is 0-5; R is H or lower alkyl and A is H, --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH.sub.2 OH or an ether or ester derivative thereof, or --CHO or an acetal derivative thereof, or --COR.sub.2 or a ketal derivative thereof where R.sub.2 is --(CH.sub.2).sub.m CH.sub.3 where m is 0-4; or a pharmaceutically acceptable salt.
Abstract: This invention relates to novel dihydroartemisinin derivatives, including their pharmaceutically-acceptable salts, which are therapeutically-effective in the pre- and post-treatment of malarial infections.
Type:
Grant
Filed:
August 20, 1987
Date of Patent:
December 13, 1988
Assignee:
The United States of America as represented by the Secretary of the Army
Inventors:
Ai J. Lin, Daniel L. Klayman, Wilbur K. Milhous
Abstract: Ion-selective compositions which comprise an ion carrier, a compound capable of solvating the ion carrier, and a supporting matrix are disclosed. The ion carrier useful in this invention is a hemispherand compound represented by the structure: ##STR1## wherein X.sub.1, X.sub.2, X.sub.3 and X.sub.4 are independently alkyl or alkenyl, or any one of X.sub.1, X.sub.2, X.sub.3 and X.sub.4 is taken with one of the others of X.sub.1, X.sub.2, X.sub.3 and X.sub.4 to form an alkylene group or an alkylene group interrupted with hetero atoms; and R represents the atoms necessary to complete a macrocyclic ring structure having from 16 to 19 atoms in the backbone of the ring structure, with the proviso that R contains (a) at least one coordinating site for sodium ions and (b) at least two alkylene groups as part of the ring structure. These compounds and the compositions containing same are particularly useful in ion-selective electrodes.
Abstract: Blue vat dyes are obtained by reaction of dihydroxydibenzanthrone and an aldehyde in chlorosulfonic acid. These dyes can be optionally chlorinated and/or substituted by sulfonamido groups. They are suitable in particular for dyeing cellulose fibres.
Abstract: This invention relates to novel tricyclic ethers, pharmaceutically acceptable addition salts and optical isomers therefrom. The compounds described herein are useful as psychotropic agents in the treatment of depression and anxiety. Also included herein are methods of preparing said compounds, pharmaceutical compositions including them and methods of treating human or animal beings by administering these pharmaceutical compositions.
Abstract: There is provided a new class of crown ethers characterized by an --OH functional group attached to a carbon atom in the heterocyclic ether ring portion and derivatives thereof. A novel process for making such crown ethers is also provided which is characterized by reacting a bisphenol ether with an epihalohydrin to effect ring closure and provide the appendant --OH group.These products are especially useful as complexing agents.