Spiro Patents (Class 549/264)
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Patent number: 6124477Abstract: The present inventor has discovered chemical compounds which inhibit the first-pass effect of orally administered drugs in humans; that phototoxic low molecular weight furocoumarins and certain ether-substituted furocoumarins that are naturally present in citrus extracts, juices, byproducts, etc. may be removed therefrom or reduced in concentration without destroying the first-pass effect inhibiting compounds therein, and a method for preparing citrus-based compositions using only FDA or USP acceptable reagents.Type: GrantFiled: December 30, 1997Date of Patent: September 26, 2000Assignee: Bioavailability Systems, LLCInventor: James W. Harris
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Patent number: 6063809Abstract: Safe, effective first-pass inhibiting compounds and citrus-derived substances are provided. Formulations containing the compounds are also provided as are methods for inhibiting the first pass effect.Type: GrantFiled: December 23, 1997Date of Patent: May 16, 2000Assignee: Bioavailability Systems, LLCInventor: James W. Harris
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Patent number: 6054477Abstract: Safe, effective first-pass inhibiting compounds and citrus-derived substances are provided. Formulations containing the compounds are also provided as are methods for inhibiting the first pass effect.Type: GrantFiled: February 23, 1999Date of Patent: April 25, 2000Assignee: Bioavailability Systems, LLCInventor: James W. Harris
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Patent number: 5989566Abstract: The invention relates to certain stable vaccine compositions comprising a macrocyclic lactone compound, a milbemycin compound, an avermectin compound or mixtures thereof; at least one antigen; a dispersing agent; an adjuvant; a water soluble organic solvent; and saline or water or mixtures thereof. The invention further relates to stable compositions as described above of a macrocyclic lactone compound, a milbemycin compound, an avermectin compound or mixtures thereof, but without an antigen. The invention also relates to a method for preventing or controlling helminthiasis, infection by acarids and arthropod endo-and ectoparasites and bacterial and viral disease in warm-blooded animals by the parenteral administration of compositions of the invention. The invention further relates to a process for the preparation of the invention compositions.Type: GrantFiled: June 28, 1996Date of Patent: November 23, 1999Assignee: American Cyanamid CompanyInventors: Ramune Marija Cobb, Christopher Leigh Schwartzkoff
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Patent number: 5990154Abstract: This invention relates to the process of making citrus (preferably grapefruit) extract having reduced levels of phototoxic furocoumarins and containing enhanced amounts of one or more anti-first pass effect compounds.Type: GrantFiled: May 22, 1998Date of Patent: November 23, 1999Assignee: Bioavailability Systems, L.L.C.Inventor: James W. Harris
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Patent number: 5962659Abstract: Novel compounds of formula (I): ##STR1## wherein R.sup.1 is hydrogen or optionally protected hydroxy; R.sup.2 is alkoxy, optionally protected hydroxy, oxo or optionally O-substituted oximino; R.sup.3 is hydrogen, optionally protected hydroxy,or a group 4'-(.alpha.-L-oleandrosyl)-.alpha.-L-oleandrosyloxy or .alpha.-L-oleandrosyloxy wherein the terminal hydroxy group is optionally protected; R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are the same or different and each is hydrogen or an organic radical; and R.sup.8 is an optionally substituted amino or imino group such as optionally O-substituted oxyimino, optionally N-substituted hydrazone, or optionally N-substituted semicarbazone; are useful in the treatment of helminthiasis in humans and animals.Type: GrantFiled: November 29, 1991Date of Patent: October 5, 1999Assignee: Pfizer, Inc.Inventors: Geoffrey Harold Baker, Roderick John Dorgan, David Owen Morgan, Peter Robin Shelley, Simon Edward Blanchflower
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Patent number: 5883080Abstract: Antiparasitic avermectin derivatives of formula (I), where the broken line represents an optional bond, R.sup.1 and R.sup.4 are independently H, OH, halo, oximino, or an organic radical, R.sup.2, R.sup.6 and R.sup.7 are organic radicals and R.sup.3 is alpha-oleandrosyl or 4'-(alpha-oleandrosyl)-alpha-oleandrosyl optionally substituted at the 4'- or 4"-position, and R.sup.12 and R.sup.13 are independently H, CN, CONH.sub.2, C.sub.1 -C.sub.8 alkyl or aryl optionally substituted with at least one halo, OH, C.sub.1 -C.sub.8 alkylthio group.Type: GrantFiled: January 16, 1998Date of Patent: March 16, 1999Assignee: Pfizer Inc.Inventors: Christopher James Dutton, Stephen Paul Gibson, Michael John Witty
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Patent number: 5871938Abstract: 1,2-dioxetane compounds bearing a proteolytic enzyme specific amino acid or peptide are provided, which amino acid or peptide can be removed by action of the corresponding protease. When the amino acid or peptide is removed, the 1,2-dioxetane decomposes with chemiluminescence, the generation of light providing a rapid, ultra-sensitive and convenient means for detecting the presence of the protease in the sample being inspected. The amount of light generated, or degree of chemiluminescence, can be correlated with the amount of protease present. Immunoassays, as well as DNA hybridization and DNA probe assays are provided.Type: GrantFiled: September 22, 1997Date of Patent: February 16, 1999
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Patent number: 5861518Abstract: This invention provides processes for producing phthalide compounds which comprise cultivating Phanerochaete avelutina FERM BP-4787 and then isolating phthalide compounds from the fermentation broth.Type: GrantFiled: October 31, 1997Date of Patent: January 19, 1999Inventors: Koenraad A. Dekker, Yuji Yamauchi, Taisuke Inagaki, Shinichi Sakemi, Nakao Kojima
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Patent number: 5861429Abstract: Compounds of formula (I): ##STR1## wherein: R.sup.1 is methyl, ethyl, isopropyl or sec-butyl; X is carbonyl or methylene; Z is .dbd.C.dbd.(R.sup.2).sub.2 or .dbd.C.dbd.(CH.sub.2).sub.m, in which R.sup.2 is alkyl, and m is integer of from 2 to 5); n is 0 or 1; R.sup.3 is nitro, amino, alkylamino, dialkylamino, alkoxy, alkoxyalkoxy, or a group (iii), (iv), (v), (vi), (vii), (viii) or (ix): ##STR2## , wherein: R.sup.4 represents: alkyl; substituted alkyl; cycloalkyl having from 3 to 6 carbon atoms; substituted cycloalkyl; alkenyl; alkynyl; carbocyclic aryl; or heterocyclic; R.sup.5 is hydrogen atom or alkyl; R.sup.6 represents: hydrogen; alkyl; or cycloalkyl; R.sup.7 represents: alkyl; cycloalkyl; carbocyclic aryl; or aralkyl; or R.sup.6 and R.sup.7, together with the nitrogen atom to which they are attached, are fuised to form heterocyclic ring; Y is oxygen or sulfur; r is 1, 2 or 3; Q is methylene or carbonyl; R.sup.8 is: alkyl or carbocyclic aryl; R.sup.Type: GrantFiled: September 30, 1996Date of Patent: January 19, 1999Assignee: Sankyo Company, LimitedInventors: Kazuo Sato, Akio Saito, Toshimitsu Toyama
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Patent number: 5843681Abstract: 1, 2-dioxetane compounds bearing a proteolytic enzyme specific amino acid or peptide are provided, which amino acid or peptide can be removed by action of the corresponding protease. When the amino acid or peptide is removed, the 1,2-dioxetane decomposes with chemiluminescence, the generation of light providing a rapid, ultra-sensitive and convenient means for detecting the presence of the protease in the sample being inspected. The amount of light generated, or degree of chemiluminescence, can be correlated with the amount of protease present. Immunoassays, as well as DNA hybridization and DNA probe assays are provided.Type: GrantFiled: October 11, 1996Date of Patent: December 1, 1998
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Patent number: 5840704Abstract: The invention provides novel compounds having the formula: ##STR1## wherein R when taken individually is H; R.sup.1 when taken individually is H or OH; R and R.sup.1 when taken together represent a double bond;R.sup.2 is an alpha-branched C.sub.3 -C.sub.8 alkyl, alkenyl, alkynyl, alkoxyalkyl or alkylthioalkyl group; a C.sub.3 -C.sub.8 cycloalkyl, C.sub.5 -C.sub.8 cycloalkenyl or C.sub.5 -C.sub.8 cycloalkylalkyl group, any of which may be substituted by methylene or one or more C.sub.1 -C.sub.4 alkyl groups or halo atoms; or a 3 to 6 membered oxygen or sulphur containing heterocyclic ring which may be substituted by one or more C.sub.1 -C.sub.4 alkyl groups or halo atoms;R.sup.3 is hydrogen or methyl;R.sup.4 is H or 4'-(alpha-L-oleandrosyl)-alpha-L-oleandrosyloxy with the proviso that when R.sup.2 is alkyl it is not isopropyl or sec-butyl; when R.sup.4 is H, each of R and R.sup.1 is H, and R.sup.2 is not methyl or ethyl; and when R.sup.Type: GrantFiled: March 23, 1993Date of Patent: November 24, 1998Assignee: Pfizer Inc.Inventors: Stephen P. Gibson, Alexander C. Goudie, Kelvin S. Holdom, John D. Bu'Lock
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Patent number: 5830875Abstract: Novel avermectin and milbemycin derivatives are disclosed, where the C-24 and C-25 carbon atoms are substituted by hydrogen, alkyl, alkenyl, substituted alkyl or substituted alkenyl groups. These compounds can be further substituted at the 4"-, 5-, 13-, and 23-positions. The new C-24 and C-25 substituted avermect prepared by cleavage of known and suitably protected avermectin and milbemycin compounds. The new compounds are potent anti-parasitic agents, in particular, the compounds are anthelmintic, insecticidal and acaricidal agents.Type: GrantFiled: October 30, 1989Date of Patent: November 3, 1998Assignee: Merck & Co., Inc.Inventors: Helmut Mrozik, Thomas L. Shih
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Patent number: 5811034Abstract: Described are novel 7-methylidene-5-oxo-furo fused naphthopyran compounds having certain substituents at the 2 position of the pyran ring. Also described are polymeric organic host materials that contain or that are coated with such compounds.Type: GrantFiled: October 23, 1997Date of Patent: September 22, 1998Assignee: PPG Industries, Inc.Inventor: Jibing Lin
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Patent number: 5728719Abstract: The present invention is a method for controlling ectoparasites. More particularly, the invention relates to a method of treatment in which the warm blooded animal is dosed with an ovicidally effective amount of a heterocyclic nitrogen compound selected from the group represented by the formula: ##STR1## wherein R.sub.1, is either one of the following groups: ##STR2## in which R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11, R.sub.12, R.sub.13, R.sub.14, R.sub.15, R.sub.16, and R.sub.17 are, the same or different, each a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.4 alkoxy group, a C.sub.1 -C.sub.4 alkylthio group, a trifluoro methyl group or a vitro group, R.sub.18, R.sub.19, R.sub.20 and R.sub.21 are, the same or different, each a hydrogen atom or a methyl group, k is an integer of 0 to 1 and 1 is an integer of 0 to 3; R.sub.2 and R.sub.3 are, the same or different, each a hydrogen atom, a halogen atom or a methyl group; R.sub.4 is a halogen atom or a methyl group; R.sub.5 and R.sub.Type: GrantFiled: March 14, 1995Date of Patent: March 17, 1998Assignee: Virbac, Inc.Inventor: Thomas A. Miller
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Patent number: 5723488Abstract: A compound of formula (I): ##STR1## wherein the broken lines represent independently optional bonds, R.sup.1 and R.sup.2 being absent when the C.sub.22 -C.sub.23 double bond is present.Type: GrantFiled: August 12, 1996Date of Patent: March 3, 1998Assignee: Pfizer Inc.Inventor: Nigel Derek Walshe
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Patent number: 5721271Abstract: Compounds of formula (I): ##STR1## wherein R.sup.1 is hydrogen or methyl, R.sup.2 is hydrogen or (E)-2-methyl 2-butenoyloxy, and R.sup.3 is hydrogen or hydroxy, with the proviso that when R.sup.3 is hydrogen, R.sup.1 and R.sup.2 are both hydrogen, and when R.sup.2 is (E)-2-methyl 2-butenoyloxy, R.sup.1 is methyl; the compound of formula (II): ##STR2## and the compound of formula (III): ##STR3## are obtainable by the fermentation of Streptomyces E225 NCIB 12310 or Streptomyces E225B NCIB 12509. The compounds have anthelmintic utility.Type: GrantFiled: October 29, 1996Date of Patent: February 24, 1998Assignee: Pfizer Inc.Inventors: Rhona Mary Banks, Geoffrey Harold Baker, Roderick John Dorgan, Mark Edward Poulton
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Patent number: 5686484Abstract: Compounds of formula (I): ##STR1## and of formula (I).sub.w : ##STR2## in which: A represents group having one of the following formulae: ##STR3## wherein R.sup.2, R.sup.3 and R.sup.4 are independently selected from the group consisting of hydrogen atoms, halogen atoms, alkyl groups having from 1 to 4 carbon atoms, and alkoxy groups having from 1 to 4 carbon atoms;R.sup.1, R.sub.w.sup.1 and R.sub.w.sup.2 are, for example, hydrogen, halogen, cyano, nitro, optically substituted alkyl, alkoxy or alkoxyalkoxy;X or X.sub.w is hydroxy, alkanoyloxy, substituted alkanoyloxy or hydroxyimino; R.sup.3.sub.w and R.sup.4.sub.w are each hydrogen, alkyl or alkoxy; R.sup.5 and R.sup.5.sub.w are methyl, ethyl, isopropyl or sec-butyl; and salts thereof have valuable anthelmintic, acaricidal and insecticidal activities.Type: GrantFiled: March 1, 1995Date of Patent: November 11, 1997Assignees: Sankyo Co., Ltd., Ciba-Geigy CorporationInventors: Yasuhiro Morisawa, Akio Saito, Satoru Naito, Toshimitsu Toyama, Susumu Kaneko, Louis-Pierre Molleyres, Jean-Claude Gehret
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Patent number: 5677332Abstract: This invention is directed to novel antiparasitic compounds of formula (I), wherein the broken line represents an optional bond, R.sup.1 and R.sup.4 being absent when this bond is present, R.sup.1, R.sup.3, R.sup.4 are independently H, OH, halo mercapto, oxo, oximino, or an organic radical, R.sup.2 and R.sup.7 are organic radicals, R.sup.6 is H or an organic radical and R.sup.12 is OH, halo, C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.9 alkanoyloxy, or oximino optionally O-substituted by a C.sub.1 -C.sub.8 alkyl, alkenyl, alkynyl, aryl, trialkylsilyl, aralkyl or C.sub.1 -C.sub.9 alkanoyl group.Type: GrantFiled: December 22, 1995Date of Patent: October 14, 1997Assignee: Pfizer Inc.Inventor: Bernard Joseph Banks
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Patent number: 5656748Abstract: The invention relates to a process for the selective hydrogenation of avermectins with the aid of a rhodium-phosphine complex based on a hydrazine.Type: GrantFiled: February 27, 1996Date of Patent: August 12, 1997Assignee: Bayer AktiengesellschaftInventors: Dieter Arlt, Gerhard Bonse, Friedhelm Reisewitz
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Processes for the production of 13-ether derivatives of milbemycins and novel intermediates therefor
Patent number: 5625078Abstract: An intermediate useful in the synthesis of milbemycin derivatives having an ether bond at the 13-position and which is represented by the general formula (IIId): ##STR1## wherein R represents a methyl group, an ethyl group, an isopropyl group or a sec-butyl group, and R.sup.5 and R.sup.6' each individually represents a hydrogen atom or a protecting group,and related precursors as well as to a process for producing these intermediates.Type: GrantFiled: May 11, 1995Date of Patent: April 29, 1997Assignee: Sankyo Company, LimitedInventors: Mitsugi Shibano, Mutsuo Suzuki, Shunshi Kojima -
Patent number: 5616729Abstract: Triggerable dioxetanes with a fluorescent substituent bonded or tethered in the dioxetane so as to produce fluorescence from the group are described. The compounds are of the formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are carbon containing groups and wherein one of R.sub.1, R.sub.2 and R.sub.3 is a tethered fluorescent substitutent. The compounds are useful in immunoassays and in probes using enzymes or other chemicals for triggering the dioxetanes to produce light from the fluorescent molecule in the group as a signal.Type: GrantFiled: December 27, 1988Date of Patent: April 1, 1997Assignee: Board of Governors of Wayne State UniversityInventors: Arthur P. Schaap, Hashem Akhavan-Tafti
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Patent number: 5614470Abstract: 13-Substituted milbemycin derivatives having the formula (I): ##STR1## wherein: R.sup.1 is methyl, ethyl, isopropyl or sec-butyl;R.sup.2 is hydrogen or alkyl;X is (.alpha.-hydroxyimino- or .alpha.-alkoxyimino-substituted)-arylmethyl or (.alpha.-hydroxyimino- or .alpha.-alkoxyimino-substituted)-heterocyclylmethyl, N-substituted-aminophenyl or N-substituted-aminophenoxy;m is 0 or 1; and n is 0 or 1;are valuable as agricultural and horticultural anthelmintic, acaricidal and insecticidal agents.Type: GrantFiled: March 29, 1995Date of Patent: March 25, 1997Assignee: Sankyo Company, LimitedInventors: Hideo Takeshiba, Kazuo Sato, Toshiaki Yanai, Shinji Yokoi, Reiji Ichinose, Kinji Tanizawa
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Patent number: 5604182Abstract: Compounds of formula (I): ##STR1## and salts and esters thereof have valuable anthelmintic, acaricidal and insecticidal activities. Methods of preparing the compounds are also provided.Type: GrantFiled: July 11, 1994Date of Patent: February 18, 1997Assignee: Sankyo Company LimitedInventors: Yasuhiro Morisawa, Akio Saito, Toshimitsu Toyama, Susumu Kaneko
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Patent number: 5591591Abstract: 1,2-dioxetane compounds bearing a proteolytic enzyme specific amino acid or peptide are provided, which amino acid or peptide can be removed by action of the corresponding protease. When the amino acid or peptide is removed, the 1,2-dioxetane decomposes with chemiluminescence, the generation of light providing a rapid, ultra-sensitive and convenient means for detecting the presence of the protease in the sample being inspected. The amount of light generated, or degree of chemiluminescence, can be correlated with the amount of protease present. Immunoassays, as well as DNA hybridization and DNA probe assays are provided.Type: GrantFiled: February 9, 1995Date of Patent: January 7, 1997
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Patent number: 5559249Abstract: Compound of general formula V ##STR1## wherein Hal is a chlorine or bromine atom. The compounds are useful as starting materials in preparing gamma-rubromicin amino derivatives.Type: GrantFiled: May 25, 1995Date of Patent: September 24, 1996Assignee: Gruppo Lepetit SpaInventors: Aldo Trani, Clelia M. L. Dallanoce, Romeo Ciabatti
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Patent number: 5556868Abstract: Avermectin and milbemycin derivatives of formula (I) ##STR1## having a double bond at the 3-4 position and a cyano substituent at the 3-position have outstanding anthelmintic properties. They may be prepared by allowing an avermectin or milbemycin derivative having a leaving group at the 5-position, or having double bonds at the 2-3 and 4-5 positions and no substituent at the 5-position, to react with an ionic cyanide.Type: GrantFiled: September 28, 1994Date of Patent: September 17, 1996Assignee: Pfizer IncInventor: Bernard J. Banks
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Patent number: 5539089Abstract: A83543 Aglycones A83543AgA, A83543AgD, A83543AgE, and A83543AgF, and A83543 pseudoaglycones A83543PsaA2, A83543PsaB2, A83543PsaD2, and A83543PsaN2 are intermediates useful in preparation of known insecticides.Type: GrantFiled: September 7, 1994Date of Patent: July 23, 1996Assignee: DowElancoInventors: Mary C. Broughton, Lawrence Creemer, Mary L. B. Huber, Herbert A. Kirst, Jan R. Turner
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Patent number: 5530133Abstract: New naphthazarin derivatives obtained by introducing in the 7' position of Purpuromycin or .gamma.-Rubromycin an amino or a monosubstituted amino group.The compounds of the invention show antibiotic activity against Gram positive and Gram negative microorganisms, fungi and protozoa and are suitable for the treatment of vaginal infections.Type: GrantFiled: May 25, 1995Date of Patent: June 25, 1996Assignee: Gruppo Lepetit SpAInventors: Aldo Trani, Clelia M. L. Dallanoce, Romeo Ciabatti
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Patent number: 5519050Abstract: The Micronesian marine sponge Phakellia sp. has been found to contain cern key members of the antineoplastic halichondrin/halistatin family. These compounds include halichondrin B, homohalichondrin B, halistatin 1, and halistatin 3.Halistatin 3 is a newly discovered member of this family. It inhibited both the P388 leukemia cell line and selected brain, lung, colon, ovarian, renal, and melanoma type cancer cell lines with ED.sub.50 /GI.sub.50 concentrations on the order of 3.times.10.sup.-5 .mu.g/ml.Type: GrantFiled: April 7, 1995Date of Patent: May 21, 1996Assignee: Arizona Board of Regents acting on behalf of Arizona State UniversityInventors: George R. Pettit, Yoshitatsu Ichihara
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Patent number: 5510372Abstract: The present invention relates to certain antibiotic compounds, designated N787-182 compounds herein and derivatives thereof, which are antiparasitic agents, active against insect pest, acari, free-living nematodes and endo- and ectoparasites. This invention also relates to pharmaceutical and other compositions comprising such compounds, methods of using such compounds, the microorganism Streptomyces hygroscopicus ATCC 53718 and mutants or genetically transformed or recombinant form thereof, and processes for producing such compounds.Type: GrantFiled: January 27, 1995Date of Patent: April 23, 1996Assignee: Pfizer IncInventors: Mark A. Haxell, David A. Perry, Hiroshi Maeda, Junsuke Tone
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Patent number: 5506247Abstract: The present invention is directed to compounds which suppress immune responses and/or selectively inhibit complement. These compounds contain an aromatic ring and are substituted dihydrobenzofurans, spirobenzofuran-2(3H)-cycloalkanes, and their open chain intermediates. The compounds of the present invention, and the pharmaceutically acceptable salts thereof, interrupt the proteolytic processing of C5 to bioactive components, exhibit immunosuppressive activities, and have therapeutic utility in the amelioration of disease and disorders mediated by complement and/or immune activity.Type: GrantFiled: January 21, 1994Date of Patent: April 9, 1996Assignees: T Cell Sciences, Inc., The University of MississippiInventors: Robert D. Sindelar, Barton J. Bradbury, Teodoro S. Kaufman, Stephen H. Ip, Henry C. Marsh, Jr., Chew Lee
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Patent number: 5478951Abstract: The present invention provides a method for the purification of a 23-E isomer of a 23-imino derivative of a LL-F28249 compound having the structural formula I ##STR1##Type: GrantFiled: June 22, 1994Date of Patent: December 26, 1995Assignee: American Cyanamid CompanyInventor: Kenneth A. M. Kremer
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Patent number: 5475010Abstract: The present invention concerns novel naphthazarin antibiotic derivatives having general formula I ##STR1## and the pharmaceutically acceptable addition salts thereof.Type: GrantFiled: May 26, 1994Date of Patent: December 12, 1995Assignee: Gruppo Lepetit S.p.A.Inventors: Aldo Trani, Clelia M. L. Dallanoce, Romeo Ciabatti
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Patent number: 5461168Abstract: An intermediate useful in the synthesis of milbemycin derivatives having an ether bond at the 13-position and which is represented by the general formula (IIId): ##STR1## wherein R represents a methyl group, an ethyl group, an isopropyl group or a sec-butyl group, and R.sup.5 and R.sup.6' each individually represents a hydrogen atom or a protecting group,and related precursors as well as to a process for producing these intermediates.Type: GrantFiled: August 31, 1993Date of Patent: October 24, 1995Assignee: Sankyo Company, LimitedInventors: Mitsugi Shibano, Mutsauo Suzuki, Shunshi Kojima
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Patent number: 5436355Abstract: Their is disclosed a novel solvent-depletion process for making an avermectin/zein composition and the composition itself, which has excellent photostability and unexpected bioavailability to foliar-feeding insects. The process consists of depleting a dilute acidic, basic or alcoholic solvent from an emulsified solution of avermectin, zein, and dilute solvent.Type: GrantFiled: February 3, 1994Date of Patent: July 25, 1995Assignee: Merck & Co., Inc.Inventor: Richard J. Demchak
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Patent number: 5428034Abstract: Compounds of formula (I): ##STR1## thereof have valuable anthelmintic, acaricidal and insecticidal activities.Type: GrantFiled: June 9, 1993Date of Patent: June 27, 1995Assignees: Sankyo Co., Ltd., Ciba-Geigy CorporationInventors: Yasuhiro Morisawa, Akio Saito, Toshimitsu Toyama, Susumu Kaneko
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Patent number: 5420260Abstract: An improved process for formation of a 5-oxime on avermectin derivatives comprises the treatment of the oxo-compound with hydroxylamine in aqueous isopropanol at pH 1.8-2.1.Type: GrantFiled: September 29, 1993Date of Patent: May 30, 1995Assignee: Merck & Co., Inc.Inventors: Joseph S. Amato, Raymond Cvetovich
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Patent number: 5411946Abstract: Avermectin derivatives, wherein the C-17-21-25-dioxaspirane substructure has been modified to include substitutions of heteratomic nucleophilic thiols at the 23,24-.alpha.-epoxide. These compounds can be similarly substituted at the 4"-, 5-, 13, and 25-positions. The new C-23 and C-24 substituted avermectin derivatives are potent anthelmintic, insecticidal and acaricidal agents.Type: GrantFiled: February 24, 1993Date of Patent: May 2, 1995Assignee: Merck & Co., Inc.Inventors: Ronald C. Newbold, Thomas L. Shih
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Patent number: 5405867Abstract: Compounds having a 16-membered macrolide ring, and related to the milbemycins and avermectins, with substituents at positions 5.13, 25 and optionally also 23, have acaricidal, insecticidal and anthelmintic properties. They are useful for treating various pests in plants and animals.Type: GrantFiled: October 8, 1993Date of Patent: April 11, 1995Assignee: Sankyo Company, LimitedInventors: Kazuo Sato, Toshiaki Yanai, Takao Kinoto, Keiji Tanaka, Akira Nishida, Toshimitsu Toyama, Bruno Frei, Anthony O'Sullivan
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Patent number: 5399717Abstract: A stereocontrolled glycosidation with thiophenyl 4-(N-allyloxycarbonyl)-epi-methylamino-4-deoxyoleandrose and 5-O-allyloxycarbonyl avermectin B.sub.1 monosaccharide using N-iodosuccinimide produces exclusively the .alpha.-anomer of a precursor of 4"-epi-methylamino-4"-deoxyavermectin B.sub.1 in 90% yield. Deprotection and crystallization as the benzoic acid salt yields 4"-epi-methylamino-4"-deoxyavermectin B.sub.1 (emamectin benzoate), a potent insecticide.Type: GrantFiled: September 29, 1993Date of Patent: March 21, 1995Assignee: Merck & Co., Inc.Inventors: Raymond Cvetovich, Mallory F. Loewe
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Patent number: 5384078Abstract: A soluble highly reactive form of calcium, prepared from Ca(II) salts and a reducing agent in ethereal, polyethereal, or hydrocarbon solvents, is presented. This form of calcium can be used in the preparation of organocalcium reagents. The organocalcium reagents resulting from the reaction of the soluble highly reactive calcium with organic compounds containing either halide, cyanide, a 1,3-diene, or a polyunsaturated functionality, are stable, useful reagents for organic synthesis. The organocalcium halide reagents undergo Grignard-type reactions. They also undergo reactions with Cu(I) salts to form organocalcium cuprate reagents. The organocalcium cuprate reagents undergo a variety of cross-coupling reactions. The soluble highly reactive calcium reacts with 1,3-dienes to yield the corresponding 2-butene-1,4-diylcalcium complexes. These bis-organocalcium reagents can undergo dialkylation reactions with .alpha.,.omega.Type: GrantFiled: December 15, 1993Date of Patent: January 24, 1995Assignee: Board of Regents of the University of NebraskaInventor: Reuben D. Rieke
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Patent number: 5380838Abstract: There is disclosed a novel form of avermectin compounds wherein the avermectin compounds are crystallized as alcohol solvates to greatly enhance stability of the avermectin drug during long-term storage. The avermectin compounds have utility as highly potent antiparasitic, insecticidal, and anthelmintic agents and compositions for that use are also disclosed.Type: GrantFiled: October 8, 1993Date of Patent: January 10, 1995Assignee: Merck & Co. Inc.Inventors: Joseph S. Amato, Raymond Cvetovich
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Patent number: 5376678Abstract: By carrying out the fermentation of Streptomyces avermitilis ATCC 55278, a dried mycelium is obtained which, orally administered to animals, particularly to ovines, has an antiparasitic activity.Type: GrantFiled: April 30, 1993Date of Patent: December 27, 1994Assignees: Gnosis srl, Euroresearch srlInventors: M. Leonardo Cappelletti, Giacomo Lucarelli, Giuseppe Mearelli
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Patent number: 5366986Abstract: The present invention is directed to compounds which suppress immune responses and/or selectively inhibit complement. These compounds contain an aromatic ring and are substituted dihydrobenzofurans, spirobenzofuran-2(3H)-cycloalkanes, and their open chain intermediates. The compounds of the present invention, and the phamaceutically acceptable salts thereof, interrupt the proteolytic processing of C5 to bioactive components, exhibit immunosuppressive activites, and have therapeutic utility in the amelioration of disease and disorders mediated by complement and/or immune activity.Type: GrantFiled: December 6, 1990Date of Patent: November 22, 1994Assignees: T Cell Sciences, Inc., The University of MississippiInventors: Robert D. Sindelar, Barton J. Bradbury, Teodoro S. Kaufman, Stephen H. Ip, Henry C. Marsh, Jr., Chew Lee
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Patent number: 5360917Abstract: A process for recovering at least one Antibiotics S541 compound or chemical derivative thereof from solution in an organic solvent, which comprises the steps of contacting the said solution with alumina and adsorbing the compound(s) thereon, eluting the compound(s) and collecting the eluate containing the compounds(s).This method is suitable for the large scale separation of individual S541 compounds or mixtures thereof.Type: GrantFiled: July 27, 1989Date of Patent: November 1, 1994Assignee: Glaxo Group LimitedInventors: Robert Thornton, David T. Eastlick, Kenneth Briggs
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Patent number: 5352804Abstract: An intensive long-term investigation of marine organisms as sources of new anticancer drugs has led to the isolation and structural elucidation (primarily by high field NMR and mass spectrometry) of halistatin 2, a new polyether macrolide of the halipyran-type, from the Western Indian Ocean sponge Axinella cf. carteri (Dendy). Halistatin 2 (1.4.times.10.sup.-6 % yield) caused the accumulation of cells arrested in mitosis, inhibited tubulin polymerization, and inhibited the binding of radiolabeled vinblastine and GTP to tubulino. Further, Halistatin 2 displayed significant activity against selected human tumor cell lines.Type: GrantFiled: January 19, 1993Date of Patent: October 4, 1994Assignee: Arizona Board of Regents, a body corporate, acting on behalf of Arizona State UniversityInventors: George R. Pettit, Feng Gao
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Patent number: 5350742Abstract: Avermectin derivatives are disclosed which incorporate two fluorine atoms at the 4' monosaccharide position, the 4" disaccharide position or the 23 position. Avermectin aglycone derivatives are also disclosed which incorporate two fluorine atoms at position 13 or 23. These difluoro avermectin analogs are derived from corresponding ketones and enones which in turn are prepared by chemical modification of naturally occurring avermectins. These compounds are used as antiparisitic, insecticidal and antihelmintic agents in humans and animals and compositions containing such compounds as the active ingredient thereof are also disclosed.Type: GrantFiled: June 10, 1993Date of Patent: September 27, 1994Assignee: Merck & Co., Inc.Inventors: Peter T. Meinke, Helmut Mrozik, Michael H. Fisher
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Patent number: 5346918Abstract: Compounds of formula (I): ##STR1## in which: R.sup.1 is a variety of organic groups; R.sup.5 is methyl, ethyl, isopropyl or sec-butyl; and X is hydroxy, alkanoyloxy or hydroxyimino and salts and esters thereof have valuable anthelmintic, acaricidal and insecticidal activities. Methods of preparing the compounds are also provided.Type: GrantFiled: February 27, 1991Date of Patent: September 13, 1994Assignee: Sankyo Company LimitedInventors: Yasuhiro Morisawa, Akio Saito, Toshimitsu Toyama, Susumu Kaneko
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Patent number: 5338865Abstract: Novel chemical compounds that can be used to synthesize halichondrin B and norhalichondrin B, and related derivatives, are described. The synthesis of halichondrin B and norhalichondrin B from these compounds also is described.Type: GrantFiled: January 29, 1993Date of Patent: August 16, 1994Assignee: President and Fellows of Harvard CollegeInventors: Yoshito Kishi, Francis G. Fang, Craig J. Forsyth, Paul M. Scola, Suk K. Yoon