The Nitrogen Is Bonded Directly At 4- Or 6-position Patents (Class 544/317)
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Patent number: 6124306Abstract: The subject invention relates to pyrimidine-thioalkyl and alkylether compounds of Formula I ##STR1## and pyrimidine-thioalkyl and alkylethers of Formula I, where R.sub.4 is selected from the group consisting of --H or --NR.sub.15 R.sub.16 where R.sub.15 is --H and R.sub.16 is --H, C.sub.1 -C.sub.6 alkyl, --NH.sub.2 or R.sub.15 and R.sub.16 taken together with the --N form 1-pyrrolidino, 1-morpholino or 1-piperidino; andR.sub.6 is --S--C.sub.1-6 alkyl (preferably --SCH.sub.3);The compounds of Formula I are useful in the treatment of individuals who are HIV positive.Type: GrantFiled: September 21, 1998Date of Patent: September 26, 2000Assignee: Pharmacia & Upjohn CompanyInventors: Joel Morris, Wade J. Adams, Janice M. Friis, Donn G. Wishka
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Patent number: 6096891Abstract: N,N'-dialkylurea and an .alpha.,.beta.-unsaturated nitrile are reacted to form a cyclic N,N'-dialkylurea containing an imine group on a ring carbon. This compound is useful as an intermediate in the formation of N,N'-dialkylpropyleneureas by hydrogenation followed by hydrogenolysis to remove the imine group. Using N,N'-dimethylurea and acrylonitrile as the starting materials one can arrive at N,N'-dimethylpropyleneurea which is a compound useful as an organic solvent and known by its acronym, DMPU.Type: GrantFiled: December 9, 1999Date of Patent: August 1, 2000Assignee: Air Products and Chemicals, Inc.Inventors: Richard V. C. Carr, Kristen Elaine Minnich, John Anthony Marsella
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Patent number: 6093718Abstract: This invention concerns heterocyclic derivatives which are useful in inhibiting oxido-squalene cyclase, processes for their preparation and pharmaceutical compositions containing them. The present invention is also concerned with heterocyclic derivatives capable of inhibiting cholesterol biosynthesis and hence in lowering cholesterol levels in blood plasma. The present invention also relates to methods of using such heterocyclic derivatives in diseases and medical conditions such as hypercholesterolemia and atherosclerosis.Type: GrantFiled: February 12, 1999Date of Patent: July 25, 2000Assignee: Zeneca LimitedInventors: David Waterson, Elaine Sophie Elizabeth Stokes, George Robert Brown, Nicholas John Newcombe
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Patent number: 6075143Abstract: There are described N-ethylglycine derivatives of the formula I ##STR1## in which PG is a urethane-type or trityl-type amino protective group which is labile to weak acids, X is NH, O or S, Y is CH.sub.2, NH or O, and B' are bases customary in nucleotide chemistry, the exocyclic amino or hydroxyl groups of which being protected by suitable, known protective groups, or are base substitute compounds, and their salts with tert-organic bases, as well as a process for their preparation. The N-ethylglycine derivatives of the formula I are used in the preparation of PNA and PNA/DNA hybrids.Type: GrantFiled: March 13, 1995Date of Patent: June 13, 2000Assignee: Hoechst AktiengesellschaftInventors: Gerhard Breipohl, Eugen Uhlmann, Jochen Knolle
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Patent number: 6071922Abstract: A method and composition for the treatment of HIV infection, HBV infection, or abnormal cellular proliferation in humans and other host animals is disclosed that includes the administration of an effective amount of a 1,3-oxaselenolane nucleoside or a pharmaceutically acceptable salt thereof, optionally in a pharmaceutically acceptable carrier.Type: GrantFiled: March 19, 1998Date of Patent: June 6, 2000Assignees: Emory University, The University of Georgia Research Foundation, Inc.Inventors: Raymond F. Schinazi, Chung K. Chu, Jinfa Du
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Patent number: 6069250Abstract: The present invention relates to methods and compositions for preparing biologically important nucleoside analogues containing 1,3-dioxolane sugar rings. In particular, this invention relates to the stereoselective synthesis of the beta (cis) isomer by glycosylating the base with an intermediate of formula (II) below a temperature of about -10.degree. C. ##STR1## wherein R.sub.1 and L are as defined herein.Type: GrantFiled: February 17, 1999Date of Patent: May 30, 2000Assignee: Biochem Pharma Inc.Inventors: Tarek Mansour, Alex Cimpoia, Krzysztof Bednarski
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Patent number: 6069252Abstract: A process for the resolution of a racemic mixture of nucleoside enantiomers that includes the step of exposing the racemic mixture to an enzyme that preferentially catalyzes a reaction in one of the enantiomers. The nucleoside enantiomer (-)-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane is an effective antiviral agent against HIV, HBV, and other viruses replicating in a similar manner.Type: GrantFiled: June 7, 1995Date of Patent: May 30, 2000Assignee: Emory UniversityInventors: Dennis C. Liotta, Raymond F. Schinazi, Woo-Baeg Choi
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Patent number: 6066732Abstract: 4(3H)-X-7H-Pyrrolo[2,3-d]pyrimidines in which X is .dbd.O or .dbd.NH are prepared by treating a 6-amino-4(3H)-X-pyrimidine with a unsubstituted or substituted 1-nitroalk-1-ene to yield a 6-amino-4(3H)-X-pyrimidine which is substituted in the 5-position by a 1-nitroalk-2-yl group; (ii) converting the 5-(1-nitroalk-2-yl)-6-amino-4(3H)-X-pyrimidine to the corresponding 5-(1-oxoalk-2-yl)-6-amino-4(3H)-X-pyr-imidine; and (iii) removing the elements of water from the 5-(1-oxoalk-2-yl)-6-amino-4(3H)-X-pyrimidine to effect cyclization.Type: GrantFiled: August 21, 1998Date of Patent: May 23, 2000Assignee: The Trustees of Princeton UniversityInventors: Edward C. Taylor, Bin Liu
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Patent number: 6063787Abstract: The present invention relates to the use of (-)-(2S,4S)-1-(2-hydroxymethyl-1,3-dioxolan-4-yl) cytosine to treat psoriasis, genital warts and other hyperproliferative keratinocyte diseases such as hyperkeratosis, ichthyosis, keratoderma or lichen planus.Type: GrantFiled: January 26, 1998Date of Patent: May 16, 2000Assignees: The University of Georgia Research Foundation Center, Yale UniversityInventors: Chung K. Chu, Yung-Chi Cheng
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Patent number: 6051709Abstract: The invention relates to a diastereoselective process for the preparation of compounds of formula (I), wherein W is S, S.dbd.O, SO.sub.2 or O; X is S, S.dbd.O, SO.sub.2 or O; R.sub.1 is hydrogen or acyl, and R.sub.2 is a purine or pyrimidine base or an analogue or derivative thereof.Type: GrantFiled: December 24, 1996Date of Patent: April 18, 2000Assignee: Glaxo Group LimitedInventors: Michael David Goodyear, P. Owen Dwyer, Malcolm Leithead Hill, Andrew Jonathan Whitehead, Roy Hornby, Peter Hallett
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Patent number: 6043248Abstract: The subject invention relates to pyrimidine-thioalkyl and alkylether compounds of Formula (I) and pyrimidine-thioalkyl and alkylethers of Formula (IA), namely the compounds of Formula (I) where R.sub.4 is selected from the group consisitng of --H or --NR.sub.15 R.sub.16 where R.sub.15 is --H and R.sub.16 is --H, C.sub.1 -C.sub.6 alkyl, NH.sub.2 or R.sub.15 and R.sub.16 taken together with the --N form 1-pyrrolidino, 1-morpholino or 1-piperidino; and R.sub.6 is selected from the group consisting of --H, or halo (preferably --Cl); with the overall proviso that R.sub.4 and R.sub.6 are not both --H. The compounds of Formula (IA) are useful in the treatment of individuals who are HIV positive being inhibitors of viral reverse transcriptase.Type: GrantFiled: October 17, 1997Date of Patent: March 28, 2000Assignee: Pharmacia & Upjohn CompanyInventors: Richard A. Nugent, Stephen T. Schlachter, Michael J. Murphy, Joel Morris, Richard C. Thomas, Donn G. Wishka, Gary J. Cleek, David R. Graber
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Patent number: 6034087Abstract: Nucleoside derivatives represented by formula (I); ##STR1## wherein, R.sub.1 represents hydrogen, phosphate or phosphonate group, R.sub.2 represents substituted or unsubstituted pyrimidine or purine base, and Z represents S, SO, SO.sub.2, O or C; or pharmaceutically acceptable salts thereof. Compound (I) can be obtained by reacting a compound of the formula (II); ##STR2## wherein, R.sub.7 represents hydrogen or hydroxy-protecting group, L represents aromatic or nonaromatic acyl, halide or alkoxy, and Z represents S, SO, SO.sub.2, O or C, with a base.Type: GrantFiled: June 11, 1997Date of Patent: March 7, 2000Assignee: Chong Kun Dang Corp.Inventors: Jung Woo Kim, Chong Ryul Lee, Koo Hun Chung, Soon Kil Ahn, Kyung Hoi Cha, Hoe Joo Son, Sung Jo Choi, Byeong Seon Jeong, Kyeong Bok Min
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Patent number: 6030976Abstract: The present invention is concerned with compounds of formula I ##STR1## wherein Z, R.sup.1 and R.sup.2 are as defined herein, as well as their pharmaceutically acceptable salts as therapeutically active substances against central nervous system disorders and for the production of corresponding medicaments.Type: GrantFiled: June 3, 1998Date of Patent: February 29, 2000Assignee: Hoffman-La Roche Inc.Inventors: Michael Bos, Thierry Godel, Claus Riemer, Andrew Sleight
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Patent number: 6017923Type: GrantFiled: May 31, 1996Date of Patent: January 25, 2000Assignee: Hoechst Marion Roussel, Inc.Inventors: Jeffrey S. Sabol, Sai P. Sunkara, Shawn C. Miller
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Patent number: 6005096Abstract: A compound having the structure ##STR1## wherein R.sup.1 is H or a linker group; R.sup.24 is independently halo or C.sub.1 -C.sub.2 haloalkyl;R.sup.25 is independently --SH, --OH, .dbd.S or .dbd.O;A is independently N or C; andM, taken together with the radical --A--C(--R.sup.25), completes an aryl or heteroaryl ring structure comprising 5 or 6 ring atoms wherein the heteroaryl ring comprises a single O ring heteroatom, a single N ring heteroatom, a single S ring heteroatom, a single O and a single N ring heteroatom separated by a carbon atom, a single S and a single N ring heteroatom separated by a carbon atom, 2 N ring heteroatoms separated by a carbon atom, or 3 N ring heteroatoms at least two of which are separated by a carbon atom, and wherein the aryl or heteroaryl ring carbon atoms are unsubstituted with other than H or at least 1 nonbridging ring carbon atom is substituted with R.sup.6 ;R.sup.6 is independently H, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl, NO.sub.Type: GrantFiled: May 8, 1995Date of Patent: December 21, 1999Assignee: Gilead Sciences, Inc.Inventors: Mark Matteucci, Robert J. Jones, Kuei-Ying Lin
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Patent number: 6001844Abstract: Compounds of structural Formula (I) ##STR1## and pharmacologically acceptable salts and esters thereof possess 5.alpha.-reductase inhibitory activity. These compounds inhibit 5.alpha.-reductase type 1 and type 2. The compounds of structural Formula I are useful in the systemic, including oral, and parenteral, including topical, treatment and prevention of hyperandrogenic conditions including prostatic carcinoma, benign prostatic hyperplasia, acne vulgaris, seborrhea, androgenic alopecia (also called androgenetic alopecia) which includes male- and female-pattern baldness, female hirsutism, and prostatitis. A class of compounds of the present invention are also potent antiandrogens. The present invention also relates to novel compositions containing such compounds, methods of their use and methods of their manufacture.Type: GrantFiled: March 11, 1998Date of Patent: December 14, 1999Assignee: Merck & Co., Inc.Inventors: Raman K. Bakshi, Soumya P Sahoo, Richard L. Tolman
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Patent number: 6002003Abstract: Activating groups for cyanine dyes used to label chain terminators in nucleotide sequencing, based on N-hydroxyphthalimide, are disclosed. From these activating groups, activated dyes of the present Invention are prepared which react with the derivitized nucleotide chain terminators to give a labeled chain terminator of the present Invention. The activating groups of the present Invention allow the dye-chain terminator reaction to occur at a much higher yield and with much greater selectivity for the mono-substituted product, compared with the prior art.Type: GrantFiled: April 14, 1998Date of Patent: December 14, 1999Assignee: Beckman Instruments, Inc.Inventors: Gene G.-Y. Shen, Thomas S. Dobashi
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Patent number: 5981537Abstract: The subject invention relates to pyrimidine-thioalkyl and alkylether compounds of Formula (I) and pyrimidine-thioalkyl and alkylethers of Formula (IA), namely the compounds of Formula (I) where R.sup.4 is selected from the group consisting of --H or --NR.sub.15 R.sub.16 where R.sub.15 is --H and R.sub.16 is --H, C.sub.1 -C.sub.6 alkyl, --NH.sub.2 or R.sub.15 and R.sub.16 taken together with the --N form 1-pyrrolidino, 1-morpholino or 1-piperidino; and R.sub.6 is selected from the group consisting of --H, or halo (preferably --Cl); with the overall proviso that R.sub.4 and R.sub.6 are not both --H. The compounds of Formula (IA) are useful in the treatment of individuals who are HIV positive.Type: GrantFiled: May 9, 1996Date of Patent: November 9, 1999Assignee: Pharmacia & Upjohn CompanyInventors: Richard A. Nugent, Stephen T. Schlachter, Michael J. Murphy, Joel Morris, Richard C. Thomas, Donn G. Wishka, Fritz Reusser, Gary J. Cleek, Irene W. Althaus
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Patent number: 5977367Abstract: Disclosed are compounds of the formula: ##STR1## or the pharmaceutically acceptable acid addition salts thereof, wherein: R.sub.1, R.sub.2, R.sub.3, R.sub.4 are the same or different and represent hydrogen, C.sub.1 -C.sub.6 alkyl, halogen, hydroxy, amino, cyano, nitro, trifluoromethyl, trifluoromethoxy, C.sub.1 -C.sub.6 alkoxy, --O.sub.2 CR', --NHCOR', --COR', --SO.sub.m R', where R' is C.sub.1 -C.sub.6 alkyl and wherein m is 0, 1 or 2; orR.sub.1, R.sub.2, R.sub.3, R.sub.4 independently represent --CONR'.sub.m, or --NR'.sub.m where m is 0, 1 or 2 and R' is hydrogen or C.sub.1 -C.sub.6 alkyl;R.sub.5 is hydrogen or C.sub.1 -C.sub.6 alkyl; andR represents an aminoalkyl group,which compounds are useful in the treatment of affective disorders such as schizophrenia, depression, Alzheimer's disease, movement disorders such as Parkinsonism and dystonia, and other disorders which respond to dopaminergic blockade such as substance abuse and obsessive compulsive disorders.Type: GrantFiled: January 9, 1998Date of Patent: November 2, 1999Assignee: Neurogen CorporationInventors: Jun Yuan, Xi Chen
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Patent number: 5962685Abstract: The present invention is directed to oxazole derivatives represented by the formula ?I!; ##STR1## wherein A represents a nitrogen atom or a R.sub.3 -substituted carbon atom; B represents a nitrogen atom, or an unsubstituted or X-substituted carbon atom; Z represents an oxygen atom, sulfinyl or sulfonyl; R.sub.1 and R.sub.2 represent each independently hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkoxy, C.sub.1 -C.sub.6 haloalkyl or the like; R.sub.3 represents hydrogen, C.sub.1 -C.sub.6 alkyl, halogen, nitro, formyl or acyl; X represents hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.1 -C.sub.6 haloalkyl or the like; Y represents hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.1 -C.sub.6 haloalkyl or the like; m represents an integar of 1 or 2, and n represents an integar of 1, 2, 3 or 4, and the salts thereof.Type: GrantFiled: January 28, 1997Date of Patent: October 5, 1999Assignee: Nippon Soda Co., Ltd.Inventors: Akiyoshi Ueda, Yasuyuki Miyazawa, Yoshihiko Hara, Masami Koguchi, Akihiro Takahashi, Takashi Kawana
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Patent number: 5962479Abstract: Corticotropin-releasing factor (CRF) antagonists having formulae (I), (II) or (III) wherein the dashed lines, A, B, Y, Z, G, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.16 and R.sub.17 are as defined in the description, and processes for preparing them. These compounds and their pharmaceutically acceptable salts are useful in the treatment of CNS and stress-related disorders.Type: GrantFiled: December 6, 1996Date of Patent: October 5, 1999Assignee: Pfizer Inc.Inventor: Yuhpyng Liang Chen
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Patent number: 5942535Abstract: The present invention relates to heterocyclic compounds of the formula ##STR1## in which R.sup.1 -R.sup.7, B, a and X have the meanings recited in the specification. These compounds are usable in the treatment of diseases of the rheumatoid group and for the prevention of allergically induced diseases.Type: GrantFiled: March 28, 1997Date of Patent: August 24, 1999Assignee: Merckle GmbHInventors: Stefan Laufer, Hans Gunther Striegel, Gerd Dannhardt
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Patent number: 5932730Abstract: Carboxylic acid derivatives ##STR1## where R-R.sup.6, X, Y and Z have the meanings stated in the description, and the preparation thereof, are described. The novel compounds are suitable for controlling diseases.Type: GrantFiled: March 27, 1997Date of Patent: August 3, 1999Assignee: BASF AktiengesellschaftInventors: Hartmut Riechers, Dagmar Klinge, Wilhelm Amberg, Andreas Kling, Stefan Muller, Ernst Baumann, Joachim Rheinheimer, Uwe Josef Vogelbacher, Wolfgang Wernet, Liliane Unger, Manfred Raschack
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Patent number: 5922867Abstract: The present invention relates to methods and compositions for preparing biologically important nucleoside analogues containing 1,3-dioxolane sugar rings. In particular, this invention relates to the stereoselective synthesis of the beta (cis) isomer by glycosylating the base with an intermediate of formula (II) below a temperature of about -10.degree. C. ##STR1## wherein R.sub.1 and L are defined herein.Type: GrantFiled: June 26, 1997Date of Patent: July 13, 1999Assignee: Biochem Pharma Inc.Inventors: Tarek Mansour, Alex Cimpoia, Krzysztof Bednarski
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Patent number: 5919792Abstract: This invention relates to certain novel compounds and derivatives thereof, their synthesis, and their use as vitronectin receptor antagonists. The vitronectin receptor antagonist compounds of the present invention are .alpha.v.beta.3 antagonists, .alpha.v.beta.5 antagonists or dual .alpha.v.beta.3/.alpha.v.beta.5 antagonists useful for inhibiting bone resorption, treating and preventing osteoporosis, and inhibiting restenosis, diabetic retinopathy, macular degeneration, angiogenesis, atherosclerosis, inflammation and tumor growth.Type: GrantFiled: October 28, 1997Date of Patent: July 6, 1999Assignee: Merck & Co., Inc.Inventors: Mark E. Duggan, George D. Hartman, William F. Hoffman, Nathan C. Ihle
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Patent number: 5914331Abstract: A method and composition for the treatment of HIV and HBV infections in humans is disclosed that includes administering an effective amount of 2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane, a pharmaceutically acceptable derivative thereof, including a 5' or N.sup.4 alkylated or acylated derivative, or a pharmaceutically acceptable salt thereof, in a pharmaceutically acceptable carrier.A process for the resolution of a racemic mixture of nucleoside enantiomers is also disclosed that includes the step of exposing the racemic mixture to an enzyme that preferentially catalyzes a reaction in one of the enantiomers.Type: GrantFiled: June 7, 1995Date of Patent: June 22, 1999Assignee: Emory UniversityInventors: Dennis C. Liotta, Raymond F. Schinazi, Woo-Baeg Choi
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Patent number: 5914400Abstract: The present invention relates to a method of preparing BCH-189 and various analogs of BCH-189 from inexpensive precursors with the option of introducing functionality as needed. This synthetic route allows the stereoselective preparation of the biologically active isomer of these compounds, .beta.-BCH-189 and related compounds. Furthermore, the steochemistry at the nucleoside 4' position can be controlled to produce enantiomerically-enriched .beta.-BCH-189 and its analogs.Type: GrantFiled: June 7, 1995Date of Patent: June 22, 1999Assignee: Emory UniversityInventors: Dennis C. Liotta, Woo-Baeg Choi
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Patent number: 5905082Abstract: (-)cis-4-Amino-1-(2-hydroxymethyl-1,3-oxathiolan-5-yl)-(IH)-pyrimidine-2-on e in crystalline form, in particular as needle-shaped or bypyramidyl crystals, pharmaceutical formulations thereof, methods for their preparation and their use in medicine.Type: GrantFiled: June 2, 1992Date of Patent: May 18, 1999Assignee: Glaxo Group LimitedInventors: Tony Gordon Roberts, Paul Evans
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Patent number: 5905070Abstract: A method and composition for the treatment of HIV and HBV infections in humans and other host animals is disclosed that includes the administration of an effective amount of a ?5-carboxamido or 5-fluoro!-2',3'-dideoxy-2',3'-didehydro-pyrimidine nucleoside or a ?5-carboxamido or 5-fluoro!-3'-modified-pyrimidine nucleoside, or a mixture or a pharmaceutically acceptable derivative thereof, including a 5' or N.sup.4 alkylated or acylated derivative, or a pharmaceutically acceptable salt thereof, in a pharmaceutically acceptable carrier.Type: GrantFiled: December 30, 1997Date of Patent: May 18, 1999Assignee: Emory UniversityInventors: Raymond F. Schinazi, Dennis C. Liotta
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Patent number: 5892025Abstract: A process for the resolution of a racemic mixture of nucleoside enantiomers that includes the step of exposing the racemic mixture to an enzyme that referentially catalyzes a reaction in one of the enantiomers. The nucleoside enantiomer (-)-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane is an effective antiviral agent against HIV, HBV, and other viruses replicating in a similar manner.Type: GrantFiled: July 14, 1998Date of Patent: April 6, 1999Assignee: Emory UniversityInventors: Dennis C. Liotta, Raymond F. Schinazi, Woo-Baeg Choi
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Patent number: 5883282Abstract: There is provided a 3-(3-aryloxyphenyl)-1-(substituted methyl)-s-triazine-2,4,6-oxo or thiotrione compound having the structural formula I ##STR1## Further provided are a composition and a method comprising that compound for the control of undesirable plant species.Type: GrantFiled: May 20, 1997Date of Patent: March 16, 1999Assignee: American Cyanamid CompanyInventors: Alvin Donald Crews, Jr., Philip Mark Harrington, Gary Mitchell Karp, Simon David Gill, Petra Dieterich
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Patent number: 5883253Abstract: The invention relates to a process for the prepn of ortho-sulfocarboxylic acids, which comprises: a) in a first reaction step, diazotizing an aromatic o-aminosulfonic acid in the presence of an acid and nitrite in water, in an organic solvent or in a mixture thereof, to an o-diazonium sulfonate, and, b) in a second reaction step, reacting the o-diazonium sulfonate in the presence of a palladium catalyst in water, in an organic solvent or in a mixture thereof, with carbon monoxide, under overpressure, to an aromatic o-sulfocarboxylic acid. The invention also relates to a process for the preparation of sulfonylureas using o-sulfocarboxylic acids as intermediates. Thus, 4-methoxyaniline-2-sulfonic acid was diazotized and treated with CO to give 97% 4-methoxybenzoic acid 2-sulfonic acid.Type: GrantFiled: June 19, 1997Date of Patent: March 16, 1999Assignee: Novartis AGInventors: Urs Siegrist, Manfred Muller, Jean Brunisholz
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Patent number: 5877312Abstract: This invention relates to methods for preparing alkylating agents and use of the agents prepared. In particular, this invention relates to preparation methods for hydroxy halide and organooxy halide alkylating agents and their use for alkylating cyclic urea compounds.Type: GrantFiled: December 31, 1996Date of Patent: March 2, 1999Assignee: DuPont Pharmaceuticals CompanyInventors: Prabhakar Kondaji Jadhav, George Clautice Emmett, Michael Ernest Pierce
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Patent number: 5869666Abstract: Conformationally locked 4',6'-cyclopropane-fused carboxylic nucleoside analogues. The compounds are prepared by condensing a cyclopropane-fused carbocyclic allylic alcohol with substituted purine or pyrimidine bases. The condensation products are then modified to produce the adenosine, guanosine, cytidine, thymidine, and uracil nucleoside analogues. The compounds are therapeutically useful as antimetabolites, or in the preparation of anti-metabolic agents.Type: GrantFiled: March 14, 1997Date of Patent: February 9, 1999Assignee: The United States of America as represented by the Secretary of the Department of Health and Human ServicesInventors: Victor E. Marquez, Juan B. Rodriguez, Marc C. Nicklaus, Joseph J. Barchi, Jr., Maqbool A. Siddiqui
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Patent number: 5852027Abstract: This invention includes the compounds 2'-deoxy-5-fluoro-3'-oxacytidine, (-)-2'-deoxy-5-fluoro-3'-oxacytidine, and (+)-2'-deoxy-5-fluoro-3+-oxacytidine, and pharmaceutically acceptable salts thereof for use in medical therapy, for example for the treatment or prophylaxis of an HIV infection.Type: GrantFiled: November 9, 1993Date of Patent: December 22, 1998Assignee: Emory UniversityInventors: Dennis C. Liotta, Raymond F. Schinazi, Woo-Baeg Choi
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Patent number: 5840892Abstract: A novel process for the preparation of substituted pyrimidine derivatives of the general formula: ##STR1## in which a halopyrimidine is reacted in the presence of a sulfinate with a compound selected from the series: ##STR2## The compounds of the general formula I are precursors of, for example, compounds with herbicidal activity.Type: GrantFiled: April 8, 1997Date of Patent: November 24, 1998Assignee: Lonza AGInventors: Yves Bessard, Gerhard Stucky
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Patent number: 5817811Abstract: Processes are described for preparing substituted N-ethylglycine derivatives of the formula ##STR1## in which PG is an amino protecting group which is labile towards weak acids and is of the urethane type or the trityl type, X is NH or O, and B' represents bases which are customary in nucleotide chemistry and whose exocyclic amino and/or hydroxyl groups are protected by suitable known protecting groups, and the salts thereof.Type: GrantFiled: September 3, 1996Date of Patent: October 6, 1998Assignee: Hoechst AktiengesellschaftInventors: Gerhard Breipohl, Eugen Uhlmann, David William Will
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Patent number: 5814639Abstract: The present invention relates to a method of preparing the antiviral compounds 2'-deoxy-5-fluoro-3'thiacytidine (FTC) and various prodrug analogues of FTC from inexpensive precursors with the option of introducing functionality as needed; methods of using these compounds, particularly in the prevention and treatment of AIDS; and the compounds themselves. This synthetic route allows the stereoselective preparation of the biologically active isomer of these compounds and related compounds.Type: GrantFiled: February 16, 1993Date of Patent: September 29, 1998Assignee: Emory UniversityInventors: Dennis C. Liotta, Raymond F. Schinazi, Woo-Baeg Choi
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Patent number: 5792868Abstract: Herein is disclosed a novel and industrially advantageous process for synthesizing acyclic nucleosides such as acyclovir and ganciclovir from ribonucleosides, which process comprises adding an acid catalyst and an acid anhydride to a solution of a ribonucleoside such as guanosine and an ester derivative of an acyclic sugar, and heating the mixture, whereby a transglycosilation reaction takes place between the ribose moiety of the ribonucleoside and the ester derivative of the acyclic sugar.Herein is also disclosed an industrially favorable method for the separation of 9-substituted purine nucleosides which are important intermediates for the synthesis of acyclic nucleosides such as acyclovir, ganciclovir, and the like from ribonucleosides, which method comprises crystallizing only the 9-isomer from a solution or suspension containing both a 9-substituted purine nucleoside and a 7-substituted purine nucleoside by cooling the solution or/and by adding a crystallizing solvent thereto.Type: GrantFiled: March 18, 1994Date of Patent: August 11, 1998Assignee: Ajinomoto Co., Inc.Inventors: Kunisuke Izawa, Yoshihito Koguchi, Hiroshi Shiragami
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Patent number: 5783576Abstract: New compounds of general formula (I) are provided: ##STR1## which are explained in the specification can be prepared by a variety of methods. The compounds may be used in pharmaceutical compositions.Type: GrantFiled: August 9, 1996Date of Patent: July 21, 1998Assignee: Boehringer Ingelheim KGInventors: Otto Roos, Georg Speck, Walter Losel, Dietrich Arndts, Wolf-Dietrich Bechtel
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Patent number: 5780473Abstract: Compounds of the formula ##STR1## inhibit the activity of endothelin.Type: GrantFiled: July 25, 1996Date of Patent: July 14, 1998Assignee: Bristol-Myers Squibb CompanyInventors: Natesan Murugesan, Joel C. Barrish, Philip D. Stein
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Patent number: 5763606Abstract: The present invention relates to a process for producing predominantly pure cis nucleoside analogues of formula (I), wherein X is S, or O; Y is S, CH.sub.2, O or CH(R); wherein R is azido or halogen; and R.sub.2 is a purine or pyrimidine base; via the coupling of a silylated purine or pyrimidine base in the presence of an appropriate Lewis acid with a bicyclic intermediate of formula (III) wherein Z is S or O; followed by conversion of the resulting intermediate of formula (II) to an alkyl ester and reduction to yield a compound of formula (I).Type: GrantFiled: February 2, 1995Date of Patent: June 9, 1998Assignee: BioChem Pharma, Inc.Inventors: Tarek S. Mansour, Colleen A. Evans, Haolun Jin, M. Arshad Siddiqui, Allan H. L. Tse
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Patent number: 5760038Abstract: Compounds of the formula ##STR1## in which the symbols are as defined herein, inhibit the activity of endothelin.Type: GrantFiled: February 6, 1995Date of Patent: June 2, 1998Assignee: Bristol-Myers Squibb CompanyInventors: Natesan Murugesan, Joel C. Barrish, Philip D. Stein
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Patent number: 5744600Abstract: A compound of the Formula I or Formula II ##STR1## wherein R.sup.1 and R.sup.2 are independently hydrogen, hydroxy, chlorine, fluorine, bromine, or an organic substituent having 1 to 5 carbon atoms and selected from acyloxy having a hydrocarbon stem of 1 to 4 carbon atoms, alkoxy, alkylthio, amino, alkylamino and dialkylamino;R.sup.3 and R.sup.4 are independently hydrogen, or organic phosphonic ester substituents having 1 to 12 carbon atoms and selected from alkyl, alkenyl, aryl, and aralkyl; andB is a heterocyclic group selected from the group consisting of pyrimidine, purine, triazine, deazapurine, and triazole, attached through a ring nitrogen atom thereof optionally substituted with 1 to 3 substituents selected from the group consisting of hydroxy, mercapto, amino, hydrazino, fluoro, chloro, bromo, iodo, C.sub.1 to C.sub.3 alkyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C1-C3 alkoxy, and C1-C3 alkylthio;and the pharmaceutically acceptable acid addition, metal, and amine salts thereof.Type: GrantFiled: December 16, 1994Date of Patent: April 28, 1998Assignees: Institute of Organic Chemistry and Biochemistry of the Academy of Sciences of the Czech Republic, Rega Stichting v.z.w.Inventors: Muzammil M. Mansuri, John C. Martin, Thomas W. Hudyma, Joanne J. Bronson, Louis M. Ferrara
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Patent number: 5728684Abstract: A method of ascertaining if a prodrug is useful for treating a disease is disclosed. The prodrug is acceptable if it is metabolized in liver cells by aldehyde oxidase to produce an active drug or metabolite. Prodrugs are shown equally effective in treating diseases as the active drug itself with many benefits and without as many associated side effects. Methods for treating cancers with 5-iodo-2-pyrimidinone-deoxyribose and 5-fluoro-2-pyrimidinone are also described.Type: GrantFiled: April 19, 1994Date of Patent: March 17, 1998Assignee: Yale UniversityInventors: Yung-Chi Cheng, Chien-Neng Chang
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Patent number: 5723609Abstract: Antiviral activity is exhibited by compounds having the formula ##STR1## and its pharmaceutically acceptable salts wherein R.sub.1 is ##STR2## wherein R.sub.2 is hydrogen, methyl, fluoro, chloro, bromo, iodo, hydroxy or amino; or trifluoromethyl; R.sub.5 is alkyl; R.sub.6 is hydrogen, alkyl, substituted alkyl, or aryl; and R.sub.7 and R.sub.Type: GrantFiled: March 13, 1989Date of Patent: March 3, 1998Assignee: E. R. Squibb & Sons, Inc.Inventors: William A. Slusarchyk, Robert Zahler
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Patent number: 5723473Abstract: A fungicidal compound of formula (I): ##STR1## wherein A is hydrogen, halogen, hydroxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.1-4 haloalkoxy, C.sub.1-4 alkylcarbonyl, C.sub.1-4 alkoxycarbonyl, phenoxy, nitro or cyano; and one of R.sup.1 and R.sup.2 is optionally substituted isoquinoline while the other is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, halogen or cyano.Type: GrantFiled: April 11, 1995Date of Patent: March 3, 1998Assignee: Zeneca LimitedInventor: Brian Leslie Pilkington
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Patent number: 5714606Abstract: The invention relates to pyrrolidine monomeric units and to oligomers which are joined via phosphate linkages, including phosphorothioate, phosphodiester and phosphoramidate linkages.Type: GrantFiled: August 15, 1996Date of Patent: February 3, 1998Assignee: ISIS Pharmaceuticals, Inc.Inventors: Oscar L. Acevedo, Normand Hebert
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Patent number: 5703058Abstract: A method and composition for the treatment of HIV and HBV infections in humans and other host animals is disclosed that includes the administration of an effective amount of a ?5-carboxamido or 5-fluoro!-2',3'-dideoxy-2',3'-didehydro-pyrimidine nucleoside or a ?5-carboxamido or 5-fluoro!-3'-modified-pyrimidine nucleoside, or a mixture or a pharmaceutically acceptable derivative thereof, including a 5' or N.sup.4 alkylated or acylated derivative, or a pharmaceutically acceptable salt thereof, in a pharmaceutically acceptable carrier.Type: GrantFiled: January 27, 1995Date of Patent: December 30, 1997Assignee: Emory UniversityInventors: Raymond F. Schinazi, Dennis C. Liotta
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Patent number: 5700295Abstract: The invention relates to compounds of formula ##STR1## wherein the variables have the meanings given in the claims. The compounds are suitable for use as UV absorbers for the photochemical stabilisation of undyed, dyed or printed textile fiber materials and for enhancing the sun protection factor thereof.Type: GrantFiled: October 11, 1995Date of Patent: December 23, 1997Assignee: Ciba Specialty Chemicals CorporationInventors: Francesco Fuso, Gerhard Reinert