Abstract: A taxane derivative of the formula ##STR1## wherein R.sub.1 is phenyl or substituted phenyl,R.sub.3 is CH.sub.3 O--, or CH.sub.3 CH.sub.2 O--,Z is --OT.sub.1,T.sub.1 is hydrogen, hydroxyl protecting group, or --COT.sub.2.T.sub.2 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkenyl, C.sub.1 -C.sub.6 alkynyl or monocylic aryl,Ac is acetyl, andE.sub.1 and E.sub.2 are independently selected from hydrogen and functional groups which increase the water solubility of the taxane derivative are useful as antitumor agents.
Abstract: The natural stereochemistry at the 13-position of avermectin aglycones, normally .alpha.-oriented or below the plane of the molecule, is inverted or epimerized into the .beta.-position. The procedure starts with the avermectin aglycone compounds where the 13.alpha.-hydroxy group is activated to a mesylate leaving group. The resultant 13-.alpha.-mesylate is then displaced with a cesium carboxylate and one equivalent of the respective carboxylic acid, ending with the ester group being converted to the 13-.beta.-hydroxy configuration by transesterification in high yield.
Type:
Grant
Filed:
July 1, 1992
Date of Patent:
August 31, 1993
Assignee:
Merck & Co., Inc.
Inventors:
Timothy Bill, Chris H. Senanayake, Robert D. Larsen, Sheo B. Singh, Thomas R. Vernhoeven
Abstract: 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.
Abstract: A metal alkoxide having the following formula: ##STR1## wherein T.sub.1 is hydrogen or a hydroxy protecting group, Z is --OT.sub.2, or --OCOCH.sub.3, T.sub.2 is hydrogen or a hydroxy protecting group, and M is selected from the group comprising Group IA, IIA and transition metals are useful in the preparation of biologically active derivatives of baccatin III and 10-deacetyl baccatin III.
Abstract: A taxane derivative of the formula ##STR1## wherein ##STR2## Z is --OT.sub.1, T.sub.1 is hydrogen, hydroxyl protecting group, or --COT.sub.2,T.sub.2 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkenyl, C.sub.1 -C.sub.6 alkynyl or monocylic aryl,R.sub.3 is benzoyl, substituted benzoyl or C.sub.1 -C.sub.6 alkoxycarbonyl,Ac is acetyl, andE.sub.1 and E.sub.2 are independently selected from hydrogen and functional groups which increase the water solubility of the taxane derivative are useful as antitumor agents.
Type:
Grant
Filed:
April 3, 1992
Date of Patent:
July 13, 1993
Assignee:
Florida State University
Inventors:
Robert A. Holton, Hossain Nadizadeh, Ronald J. Beidiger
Abstract: There are disclosed halogenated dioxolanes of a specified formula, dioxoles made therefrom, polymers of the dioxoles, and processes for making the dioxolanes.
Abstract: The invention relates to the benzylcyclanone derivatives of formula: ##STR1## where R.sub.1 and R.sub.3 denote H, OH, linear or branched C.sub.1 -C.sub.8 alkyl or linear or branched C.sub.1 -C.sub.8 alkoxy, R.sub.2 and R.sub.4 represent H or OH, at least one of the two being OH, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 represent H, C.sub.1 -C.sub.18 alkyl, aralkyl or aryl, it being possible for R.sub.5 and R.sub.6 and/or R.sub.7 and R.sub.8 to form an optionally substituted, saturated C.sub.5 -C.sub.12 ring, X represents O or --(CR.sub.9 R.sub.10).sub.n with n=1 or 2 and R.sub.9 and R.sub.10 represent H or CH.sub.3 ; if X represents --(CR.sub.9 R.sub.10).sub.n, R.sub.6 and R.sub.8, with the atoms of the ring to which they are attached, form a bicyclic system having 7 or 8 carbon atoms; if X represents --(CR.sub.9 R.sub.10).sub.n with n=1, R.sub.9 and R.sub.10 =CH.sub.3, R.sub.5 =H and R.sub.6 and R.sub.8, with the atoms of the ring to which are attached, form a bicyclic system having 7 carbon atoms, R.sub.
Abstract: A process for producing 3,4-dihydrocoumarin comprising cyclization and dehydrogenation of a 3-(2-cyclohexanoyl)propionic acid ester, in which a reaction mixture obtained by the cyclization and dehydrogenation is washed with an alkali to reduce the dihydrocinnamic acid content of the reaction mixture to 1% by weight or less and/or previously distilling the reaction mixture to remove high-boiling substances, and then subjected to rectification to recover 3,4-dihydrocoumarin. The thus obtained 3,4-dihydrocoumarin has high purity and high quality sufficient for use as a perfume as it is.
Abstract: The use is described of macrolactones, such as cladospolides and patulolides, as medicaments for the treatment of allergic-inflammatory diseases.
Type:
Grant
Filed:
August 19, 1991
Date of Patent:
June 8, 1993
Assignee:
Boehringer Mannheim GmbH
Inventors:
Fritz Hansske, Otto-Henning Wilhelms, Heidrun Anke
Abstract: The present invention provides novel furocoumarinsufonamide derivatives having the formula ##STR1## wherein R.sub.1, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are independently H or lower alkyl; m, n and p are independently 2, 3, 4, 5 or 6; A is NR.sub.4 (CH.sub.2).sub.P NR.sub.5, NR.sub.6, O or S; R.sub.2 is independently H, lower alkyl or a moiety of the formula ##STR2## useful for inhibiting protein kinase C and treating conditions related to, or affected by inhibition of protein kinase C, particularly cancer tumors, inflammatory disease, reperfusion injury, and cardiac dysfunctions related to reperfusion injury.
Abstract: This invention relates to compounds which are steroidyl derivatives of 4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one and the corresponding ring-opened hydroxy acid form thereof which are useful as antihypercholesterolemic agents, to pharmaceutical compositions including such compounds, and to their use in treating hypercholesterolemia.
Type:
Grant
Filed:
February 5, 1991
Date of Patent:
June 1, 1993
Assignee:
Rhone-Poulenc Rorer Pharmaceuticals Inc.
Inventors:
Daniel G. McGarry, Francis A. Volz, John R. Regan, Michael N. Chang
Abstract: Nitrato alkyl oxetanes are synthesized directly from the corresponding hyxy alkyl oxetanes by nitrating the hydroxy alkyl oxetane under non-acidic anhydrous conditions. A hydroxy alkyl oxetane is reacted with an anhydrous nitrate ester of a carboxylic acid at temperatures below about 10.degree. C. The product of the method, nitrato alkyl oxetane, is produced in relatively high yield without opening of the oxetane ring.
Type:
Grant
Filed:
July 10, 1989
Date of Patent:
May 25, 1993
Assignee:
The United States of America as represented by the Secretary of the Navy
Abstract: A process for producing high purity .alpha.-zeranol from a zeralenone containing surface fermentation product is described. One feature of the process entails fractional crystallization from an aqueous acetonitrile solvent of high purity .alpha.-zeranol from a solution containing a mixture of 50 to 60 parts by weight .alpha.-zeranol and 40 to 50 parts by weight .beta.-zeranol.
Type:
Grant
Filed:
May 7, 1992
Date of Patent:
May 11, 1993
Assignee:
C.R.C. Compagnia di Ricera Chimica S.p.A.
Abstract: Compounds of either of general formulae I and II: ##STR1## wherein: R.sup.1, R.sup.2, R.sup.3, R.sup.5, R.sup.6, a, b, c, and d are variables.These compounds are useful in the treatment of hypercholesterolaemia in general and arteriosclerosis, familial hypercholesterolaemia or hyperlipidaemia in particular.
Type:
Grant
Filed:
September 16, 1991
Date of Patent:
May 11, 1993
Assignee:
British Bio-Technology Limited
Inventors:
Richard S. Todd, Christopher N. Lewis, Alan H. Davidson, Alan H. Drummond
Abstract: Novel fluoran compounds represented by the formula (I): ##STR1## wherein R.sup.1 is an alkyl group having from 1 to 4 carbon atoms, preparation process of the fluoran compounds, and a heat-sensitive and a pressure-sensitive recording material comprising the fluoran compound, are disclosed.
Abstract: Compounds of the formula: ##STR1## where R.sup.1 is hydrogen or hydroxy and R.sup.2 is a substituted amino group, a substituted heterocyclic ring or a substituted alkyl. These compounds are oxytocin and vasopressin antagonists useful in the treatment of preterm labor, dysmenorrhea and for the stoppage of labor preparatory to cesarean delivery, timing of parturition, uterine hyperactivity, endometriosis, hypertension, congestive heart failure, hyponatremia and cognitive disorders. Also disclosed are pharmaceutical compositions containing these compounds, methods of their use and methods of their preparation.
Type:
Grant
Filed:
September 16, 1991
Date of Patent:
April 20, 1993
Assignee:
Merck & Co., Inc.
Inventors:
Mark G. Bock, Ben E. Evans, Roger M. Freidinger, Kevin Gilbert, Doug W. Hobbs, James B. Hoffman, George F. Lundell, Douglas J. Pettibone
Abstract: Taxol, 10-deacetyltaxol and other taxane derivatives are prepared from naturally occurring taxane-7-xylosides by the oxidative-cleavage of the 7-xyloside moieties.
Abstract: The present invention concerns novel dioxolane containing fluoroepoxides that are useful as curing materials, adhesives lubricants and coatings.
Abstract: Process for preparing taxol by the condensation of a (2R, 3S) acid of general formula (I) with a taxan derivative of general formula (II), followed by the removal of the groups R.sub.2 and R.sub.3 protecting the hydroxy groups .Iadd.and intermediates used therein.Iaddend..
Type:
Grant
Filed:
November 1, 1991
Date of Patent:
June 8, 1993
Assignee:
Centre National de la Recherche Scientifique
Inventors:
Jean-Noel Denis, Andrew E. Greene, Daniel Guenard, Francoise Gueritte-Voegelein