Abstract: C7, C10 di-CBZ 10-deacetyl baccatin III of the formula: ##STR1## provides an intermediate for the production of docetaxel. A method of producing this C7, C10 di-CBZ 10-deacetyl Baccatin III is provided. Here, 10-deacetyl Baccatin III is acylated with at least 1.5 equivalents of n-butyl lithium and at least 1.5 equivalents of benzyl chloroformate in tetrahydrofuran. The 10-deacetyl Baccatin III may first be dissolved in tetrahydrofuran after which the n-butyl lithium is added followed by the addition of the benzyl chloroformate. The reaction is preferably at a reduced temperature of less than -20.degree. C. The resulting solution may be quenched with ammonium chloride and reduced to residue. The residue may then be redissolved in an organic solvent, washed, dried and recrystallized to purify the compound.

Abstract: This invention relates to a taxoid of the formula (I): ##STR1## wherein R.sup.1 is a C.sub.3 -C.sub.5 alkyl or alkenyl or trifluoromethyl radical;R.sup.2 is a C.sub.3 -C.sub.5 branched alkyl radical;R.sup.3 and R.sup.4 are independently selected from hydrogen and hydroxyl protecting groups including functional groups which increase the water solubility of the taxoid antitumor agent;R.sup.5 is a hydrogen, an acyl radical, or an alkoxylcarbonyl or carbamoyl radical; andR.sup.6 is an acyl radical.The compounds of formula I are useful as antitumor agents or their precursors. This invention also relates to a pharmaceutical composition having antineoplastic activity comprising the compound of formula (I) and a physiologically acceptable carrier and method of treatment using the compound of formula I.

Abstract: This invention relates to a taxoid of the formula (I) ##STR1## wherein R.sup.1 is 1-propenyl radical;R.sup.2 is a C.sub.3 -C.sub.5 branched alkyl radical;R.sup.3 and R.sup.4 are independently selected from hydrogen and hydroxyl protecting groups including functional groups which increase the water solubility of the taxoid antitumor agent;R.sup.5 represents a hydrogen or a hydroxyl protecting group;R.sup.6 represents an acyl radical,which are useful as antitumor agents or their precursors. A pharmaceutical composition having antineoplastic activity comprising the compound of formula (I) and a physiologically acceptable carrier and method of treatment are also disclosed.

Abstract: The invention provides taxanes that are conjugates of cis-docosahexaenoic acid and taxotere. The conjugates are useful in treating cancer.

Abstract: The invention relates to thioureido-cyclodextrins, usable in particular to solubilize anti-tumor and antiparasitic agents and their preparation processes.These thioureido-cyclodextrins correspond to the formula: ##STR1## with m=6, 7 or 8, R.sup.1 represents OH or NH--CS--NHR.sup.2, at least one of the R.sup.1 being NH--CS--NHR.sup.2,R.sup.2 represents an alkyl, monosaccharide, oligosaccharide glycosyl-amino acid or glycopeptide group.These cyclodextrins are usable for solubilizing anti-tumor or antiparasitic agents of the Taxol family.

Abstract: An efficient protocol for the synthesis of taxol, taxol analogs and their intermediates is described. The process incudes the attachment of the taxol A-ring side chain to baccatin III and for the synthesis of taxol and taxol analogs with variable A-ring side chain structures. A rapid and highly efficient esterification of O-protected isoserine and 3-phenylisoserine acids having N-benzyoloxycarbonyl groups to the C-13 hydroxyl of 7-O-protected baccatin III is followed by a deprotection-acylation sequence to make taxol, cephalomanninne and various analogs, including photoaffinity labeling candidates.

Abstract: A process for preparing N-acyl, N-sulfonyl and N-phosphoryl substituted isoserine esters in which a metal alkoxide is reacted with a .beta.-lactam.

Abstract: A derivative or analog of baccatin III or 10-desacetyl baccatin III having a C-9 substituent other than keto.

Abstract: A method of acylating C-2' O-protected-10-hydroxy taxol selectively at the C-10 hydroxyl position over the C-7 hydroxy position thereof to produce C-2' O-protected taxol is accomplished first by dissolving C-2' O-protected-10-hydroxy taxol in an acceptable ether solvent therefor, such as tetrahydrofuran, to form a first solution at a first temperature. The first solution is then cooled to a second temperature, and a lithium base, preferably n-butyl lithium, is added to form an intermediate compound having a lithium alkoxide at the C-10 position thereof. An acylating agent, such as acetyl chloride, is then added. The resulting solution may be quenched, for example with ammonium chloride, to eliminate excess of the acylating agent and the lithium base. The result is a solution containing C-2' O-protected taxol. This solution may then be washed, concentrated and purified. The present invention is also directed to C-10 lithium alkoxide intermediate compounds for the production of paclitaxel.

Abstract: The present invention teaches a method of extracting TAXOL.RTM. from the leaves of taxus cupidata plants. The process comprises a series of steps, including the concentration of the extracts obtained from the plant, the separation of the aqueous and chloroform phases, and several purification procedures. In addition, the present invention teaches a multi-step process wherein the virtual removal of chlorophyll is achieved prior to the introduction of the extract into the silica gel packing material. This prevents the deactivation of the silica gel packing material by chlorophyll in the extract solution.

Abstract: Spontaneously dispersible concentrates comprising new esters of Baccatin-III, 10-Deacetylbaccatin-III and 14-OH-10-Deacetylbaccatin-III, procedures for their production. The preparation of aqueous ultramicroemulsions, their incorporation into pharmaceutical compositions having antitumor, antiviral and virucidal activity, are efficacious in the treatment of eczemae and psoriasis and stimulate the increased absorption of exogenous activators, regulators or modulators, are described.

Abstract: Taxane derivatives having an amino substituted C13 side chain.

Abstract: Provided herein is a taxane having a hydrocarbon attached at the 2' and/or 7 positions, the hydrocarbon's alpha position being occupied by a "hydrolysis-promoting group" ("HPG"). Substitution of an HPG for the methylene unit ordinarily occupying the alpha position allows for enhanced in vivo hydrolysis of the hydrocarbon-taxane bond, and hence, for enhanced taxane therapeutic activity. Also provided herein are taxane-containing compositions, and methods of administering taxanes to animals, including those afflicted with cancers.

Abstract: A method of acylating C-2' O-protected-10-hydroxy taxol selectively at the C-10 hydroxyl position over the C-7 hydroxy position thereof to produce C-2' O-protected taxol is accomplished first by dissolving C-2' O-protected-10-hydroxy taxol in an acceptable ether solvent therefor, such as tetrahydrofuran. A lithium salt, preferably lithium chloride, is added. A trialkylamine base or pyridine is next added, followed by the addition of an acylating agent, such as acetyl chloride. The resulting solution may be quenched, for example with ammonium chloride, to eliminate excess of the acylating agent. This solution may then be diluted with ethyl acetate to form an organic phase and an aqueous phase, with the organic phase being washed and thereafter reduced. Recrystallization and column chromatography may be employed to purify the C-2' O-protected taxol.

Abstract: A method for esterifying C13 deoxy taxoid intermediates employs three steps, i.e., oxygenation of the C13 deoxy taxoid intermediate to produce a C13 enone taxoid intermediate; reduction of the C13 enone to produce an alcohol; followed by esterification of the C13 alcohol. Key intermediates include C13 deoxy taxoids; C13 enone substituted taxoids; and C1-C2 cyclo carbonate esters of taxoids.

Abstract: The present invention relates to solvent-free processes for the preparation of mono-substituted fluorinated oxetane monomers. Once prepared, the mono-substituted fluorinated oxetane monomers can be used to prepare prepolymers and polymers having fluorinated alkoxymethylene side chains.

Abstract: The present invention relates to a method of obtaining different biologically pure cultures of bacteria isolated from different species of Taxus such as Taxus canadensis. T. brevifolia, T. baccata, T. cuspidata, and T. hunnewelliana, wherein the bacteria produce in vitro taxanes and paclitaxel, and wherein the bacteria are of the genus Sphingomonas, Bacillus, Pantoea or Curtobacterium. Also, the present invention relates to a method of a bacterial mass production of at least one taxane or paclitaxel. There is also disclosed a novel bacterial taxane. The present invention also relates to the use of different biologically pure cultures of bacteria isolated from different species of Taxus, wherein the bacteria are able to biotransform pro-taxanes. There is also provided a process for improving taxanes and paclitaxel production of taxanes and paclitaxel producing bacteria which include culturing bacteria in the presence of a mutagenic agent for a period a time sufficient to allow mutagenesis.

Abstract: Taxane derivatives having alternative C2 substituents.

Abstract: The present invention relates to an improved process for the production of important taxol analogues 10-deacetyl taxol A,B and C of the formula (2) ##STR1## R=C.sub.6 H.sub.5 (10 deacetyl taxol A) =CH.sub.3 C.dbd.CHCH.sub.3 (10-deacetyl taxol B)=C.sub.5 H.sub.11 (10-deacetyl taxol C)where R represent C.sub.6 H.sub.5 (10-deacetyl taxol A) or, CH.sub.3 C.dbd.CHCH.sub.3 (10-deacetyl taxol B) or, C.sub.5 H.sub.11 (10-deacetyl taxol C) which comprises (a) dissolving the taxol analogues 7-xylosyl-10-deacetyl taxol A,B,C of the formula (1) ##STR2## R=C.sub.6 H.sub.5 (10 deacetyl taxol A) =CH.sub.3 C.dbd.CHCH.sub.3 (10-deacetyl taxol B)=C.sub.5 H.sub.11 (10-deacetyl taxol C)where R represents C.sub.6 H.sub.5 (taxol analogue A or xyloside A), or CH.sub.3 C.dbd.CHCH.sub.3 (taxol analogue B or xyloside B) or C.sub.5 H.sub.11 (taxol analogue C or xyloside C) in a polar solvent (b) reacting the resultant solution with periodate for 20-40 hours at 20-40.degree. C.

Abstract: Process for the preparation of 4-acetoxy-2.alpha.-benzoyloxy-5.beta.,20-epoxy-1,7.beta., 10.beta.-trihydroxy-9-oxo-tax-11-en-13.alpha.-yl (2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-3-phenylpropionate trihydrate, characterized in that the 4-acetoxy-2.alpha.-benzoyloxy-5.beta.,20-epoxy-1,7.beta.,10.beta.-trihydro xy-9-oxo-tax-11-en-13.alpha.-yl (2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-3-phenylpropionate is crystallized from a mixture of water and an aliphatic alcohol containing 1 to 3 carbon atoms, and then the product obtained is dried under defined conditions of temperature, pressure and humidity.

Abstract: Process for synthesizing paclitaxel by treating baccatin III with a strong base in a solvent, adding an electrophile to the solution to form a 7-O-protected baccatin III derivative, reacting the 7-O-protected baccatin III derivative with a protected paclitaxel sidechain in a solvent such that the protected paclitaxel sidechain is coupled to the 13-hydroxyl of the 7-O-protected baccatin III, and subsequently deprotecting the protected paclitaxel sidechain and the 7-O protecting group to form paclitaxel, and intermediates used therein.

Abstract: Taxane derivatives having an alkoxy, alkenoxy or aryloxy substituted C13 side chain.

Abstract: The present invention relates to novel taxane derivatives wherein, the taxol ring is substituted by sulfur groups on the C-7, their use as antitumor agents and pharmaceutical formulations.

Abstract: Taxol is produced from taxol-producing micro-organisms. Methods of obtain the taxol-producing microorganisms are described. Radioactive labelled taxol products and methods for use of the radioactive labelled taxol and for the treatment of leukemia and cancer cells are described.

Abstract: Taxane derivatives having alternative C9 substituents.

Abstract: A method for purifying taxoids (Taxotere, 10-deacetylbaccatin III) by centrifugal partition chromatography.

Abstract: The synthesis of taxol and other tricyclic and tetracyclic taxanes.

Abstract: Taxane derivatives having a 3' butenyl substituted C13 side chain.

Abstract: Taxanes are purified by chromatographic separation using a phenylalkyl chromatographic resin, wherein the alkyl portion of the phenylalkyl is a C.sub.4 -C.sub.10 moiety. Taxanes such as paclitaxel, 10-deacetyltaxol, 7-epi-taxol, cephalomannine, baccatin III, baccatin V, 7-epi-DAB, 10-deactylbaccatin III ("DAB") and 9-dihydro-13-acetylbaccatin III ("DHB") and others may be purified. In accordance with the invention, taxanes are separated from each other and from other impurities common to crude taxane samples.

Abstract: A process for the preparation of 4,10-diacetoxy-2.alpha.-benzoyloxy-5.beta.,20-epoxy-1,7.beta.-dihydroxy-9- oxo-tax-11-en-13.alpha.-yl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropionate trihydrate by crystallization from a water/alcohol solution.

Abstract: Taxane derivatives having alternative C10 substituents.

Abstract: Taxane derivatives having alternative C7 substituents.

Abstract: Process for the preparation of a derivative or analog of baccatin III or 10-desacetyl baccatin III having a C9 substituent other than keto in which the C9 keto substituent of taxol, a taxol analog, baccatin III or 10-desacetyl baccatin III is selectively reduced to the corresponding hydroxy group.

Abstract: The present invention disclose to non-radioactive vitamin D compounds of formula (1) and methods to assay for the presence of vitamin D, vitamin D analogs and their metabolites which may be present in milk, blood or other biological fluids. The assay methods employed in this invention may be enzyme linked immununoassays (ELISAs) (with biotin containing compounds) and fluorimetric and chemiluminometric assays (with fluorescein or chemiluminiscence containing compounds).

Abstract: The present invention provides new methods isolating taxanes and other metabolites from taxane-producing plant materials.

Abstract: A compound of the formula I: ##STR1## wherein Ar represents an aryl radical;R.sub.1 represents a hydrogen atom, an aroyl radical, or a radical of the formula R.sub.4 --O--CO;R.sub.2 and R.sub.3 together form a 5- or 6-membered saturated heterocycle;G.sub.1 represents an acetyl radical or a protecting group of the hydroxyl functional group; andG.sub.2 represents a protecting group of the hydroxyl functional group.

Abstract: The present invention concerns novel paclitaxel derivatives, their use as antitumor agents, and pharmaceutical formulations.

Abstract: Disclosed are water soluble compositions of paclitaxel and docetaxel formed by conjugating the paclitaxel or docetaxel to a water soluble chelator, polyethylene glycol or polymer such as poly (1-glutamic acid) or poly (1-aspartic acid). Also disclosed are methods of using the compositions for treatment of tumors, auto-immune disorders such as rheumatoid arthritis and for prediction of paclitaxel uptake by tumors and radiolabeled DTPA-paclitaxel tumor imaging. Other embodiments include the coating of implantable stents for prevention of restenosis.

Abstract: The present invention relates to novel oxazolidinecarboxylic acids. These oxazolidinecarboxylic acids are useful intermediates for the esterification of taxane synthons to provide taxanes esterified with an isoserine residue.

Abstract: A chemical compound having the formula: wherein R is an alkyl group and M.sup.+ counterion is an alkali metal, and a process of making the same.

Abstract: Novel methods for the preparation of sidechain-bearing taxanes, comprising the preparation of an oxazoline compound, coupling the oxazoline compound with a taxane having a hydroxyl group directly bonded at C-13 thereof to form an oxazoline sidechain-bearing taxane, and opening the oxazoline ring of the oxazoline sidechain-bearing taxane so formed. Novel compounds prepared by the methods of the present invention are also provided.

Abstract: Novel taxoids of general formula (I), the preparation thereof, and pharmaceutical compositions containing the novel taxoids: ##STR1## wherein Z represents a hydrogen atom or a radical of general formula (II): ##STR2##

Abstract: A reaction of perfluoroolefins with bis(silyl) ethers to produce novel partially fluorinated and perfluorinated copolymers and macrocyclic compounds is disclosed.

Abstract: A high yield and high purity method for obtaining taxane analogues from a source containing taxanes. The method employs a polymeric resin membrane for separating the analogues under low pressure without the use of complex and expensive separation/purification steps currently provided in the art.

Abstract: This invention relates to a method of producing a taxane-type diterpene(s) wherein tissues or cells of a plant which produces taxane-type diterpene(s) is cultured in the presence of at least one selected from the group consisting of jasmonic acids, compounds containing a heavy metal, complex ions containing a heavy metal, heavy metal ions, amines and antiethylene agents, a method of producing a taxane-type diterpene wherein the tissues or the cells of the plant are cultured by controlling the oxygen concentration in a gas phase in a culture vessel to less than the oxygen concentration in the atmosphere from the initial stage of the culture, or by controlling the dissolved oxygen concentration in a fluid medium which is in contact with the tissue or the cell to less than the saturated dissolved oxygen concentration at that temperature from the initial stage of the culture, a method of producing a taxane-type diterpene wherein the tissue or the cell of the plant is cultured in a culture vessel, while oxygenic g

Abstract: This invention provides oxazolidine protected taxol analogs of the Formula: ##STR1## which are useful intermediates to make various taxol analogues.

Abstract: The present invention is directed compositions of the formula: ##STR1## wherein: D is a residue of biologically active moiety;X is an electron withdrawing group;Y and Y' are independently O or S;(n) is zero (0) or a positive integer, preferably from 1 to about 12;wherein: R.sub.1 and R.sub.2 are independently selected from the group consisting of H, C.sub.1-6 alkyls, aryls, substituted aryls, aralkyls, heteroalkyls, substituted heteroalkyls and substituted C.sub.1-6 alkyls;wherein: R.sub.3 is a substantially non-antigenic polymer, C.sub.1-12 straight or branched alkyl or substituted allyl, C.sub.5-8 cycloalkyl or substituted cycloalkyl, carboxyalkyl, carboalkoxy alkyl, dialkylaminoalkyl, phenylalkyl, phenylaryl or ##STR2## wherein: R.sub.4 and R.sub.5 are independently selected from the group consisting of H, C.sub.1-6 alkyls, aryls, substituted aryls, aralkyls, heteroalkyls, substituted heteroalkyls, and substituted C.sub.1-6 alkyls or jointly form a cyclic C.sub.5 -C.sub.7 ring.

Abstract: The present invention relates to a novel process for preparing dialkoxy derivatives of the taxoid family by direct alkylation of the two positions 7 and 10 of deacetylbaccatin or derivatives thereof which are esterified in position 13.

Abstract: Novel taxoids of general formula (I), wherein R is a substituted alkyl radical or an alkenyl, alkynyl, cycloalkyl, optionally substituted cycloalkenyl or phenyl radical, or an aromatic 5- or 6-membered heterocyclic radical; and Z is a hydrogen atom or a radical of general formula (II), wherein R.sub.1 is an optionally substituted benzoyl, thenoyl or furoyl radical or a radical R.sub.2 --O--CO, where R.sub.2 is an alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, bicycloalkyl, optionally substituted phenyl, or heterocycl radical, and R.sub.3 is an aromatic heterocyclic, alkyl, alkenyl, alkynyl cycloalkyl, phenyl or naphthyl radical. The novel products of general formula (I), wherein Z is a radical of general formula (II), have remarkable antitumoral activity.

Abstract: Taxol is produced from taxol-producing microorganisms. Methods of obtaining he taxol-producing microorganisms are described. Radioactive labelled taxol products and methods for use of the radioactive labelled taxol and for the treatment of leukemia and cancer cells are described.