One Double Bond Between The Ring Members Of The Oxazole Ring Patents (Class 548/237)
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Patent number: 6235901Abstract: A novel compound having the formula: wherein R is an alkyl group containing 1-5 carbon atoms or an aryl, substituted aryl, substituted or unsubstituted heteroaryl, alkyl-aryl, alkylether-aryl or O; R1 and R2 are hydrogen or a methyl group; X is O, NH, NR′ wherein R′ is an alkyl group containing 1-5 carbon atoms, or O—R″ or NR″ wherein O—R″ is O-alkyl-O or O-alkyl, NR″ is O-alkyl-ONH, wherein each instance alkyl contains 1-5 carbon atoms and n is 0 or 1. The compound of this invention is useful as a monomer which can be polymerized and/or copolymerized by catonic polymerization. Polymers and copolymers produced in this invention can be crosslinked and are useful in coatings, inks, overprint varnishes, and surface treatment applications.Type: GrantFiled: May 6, 1999Date of Patent: May 22, 2001Assignee: S. C. Johnson Commercial Markets, Inc.Inventors: Bill M. Culbertson, David L. Trumbo
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Patent number: 6231786Abstract: In the fluorinated azoles of the formula (I) R1(—A1)a—T—(A2—)b(M—A3—)cR2 (I) the symbols and indices have -the following meanings: T is undirected and is 4-fluorothiazole-2,5-diyl, 5-fluorothiazole-2,4-diyl, 4-fluorooxazole-2,5-diyl, 5-fluorooxazole-2,4-diyl or 4-fluoroisoxazole-2,5-diyl; R1 and R2 are identical or different and are hydrogen or a straight-chain or branched C1-20-alkyl or C2-20-alkenyl radical (with or without asymmetrical carbon atoms); A1, A2 and A3 are identical or different and are, for example, phenylene-1,4-diyl or cyclohexane-1,4-diyl; M is undirected and is —OC(═O)—, —OCH2—, —CH2CH2—, —OC(═O)CH2CH2—, —OCH2CH2CH2—, —C≡C—, —CH2CH2CH2CH2— or a single bond; a, b and c, independently of one another, are 0 or 1, with the proviso that the sum a+b+c is 1 or 2.Type: GrantFiled: January 18, 2000Date of Patent: May 15, 2001Assignee: Clariant GmbHInventors: Rainer Wingen, Barbara Hornung, Ayako Ogawa, Wolfgang Schmidt
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Patent number: 6228868Abstract: Compounds having Formula I are useful for treating cancer. Also disclosed are pharmaceutical compositions comprising compounds of Formula I, and methods of treating cancer in a mammal.Type: GrantFiled: July 23, 1999Date of Patent: May 8, 2001Assignee: Abbott LaboratoriesInventors: Stephen L. Gwaltney, II, Hwan-Soo Jae, Douglas M. Kalvin, Gang Liu, Hing L. Sham, Qun Li, Akiyo K. Claiborne, Le Wang, Kenneth J. Barr, Keith W. Woods
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Patent number: 6211214Abstract: The present invention relates to novel biphenyl ether-oxazolines of the formula (I) in which X, Y, Z, R1, R2, A, m and n have the meaning given in the description, to processes for their preparation and to their use for controlling animal pests, and two novel intermediate products.Type: GrantFiled: May 12, 1998Date of Patent: April 3, 2001Assignee: Bayer AktiengesellschaftInventors: Wolfgang Krämer, Udo Kraatz, Christoph Erdelen, Ulrike Wachendorff-Neumann, Andreas Turberg, Norbert Mencke
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Patent number: 6207693Abstract: This invention relates to new benzamide derivatives having a vasopressin antagonistic activity, etc. and represented by general formula (I): wherein R1 is aryl optionally substituted with lower alkoxy, etc., R2 is lower alkyl, etc., R3 is hydrogen, etc., A is NH, etc., E is etc., X is —CH═CH—, —CH═N—, or S, and Y is a condensed heterocyclic group, etc., and pharmaceutically acceptable salts thereof, to processes for preparation thereof and to a pharmaceutical composition comprising the same.Type: GrantFiled: June 2, 1999Date of Patent: March 27, 2001Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Hiroyuki Setoi, Takehiko Ohkawa, Tatsuya Zenkoh, Hitoshi Sawada, Yuki Sawada, Teruo Oku
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Patent number: 6201124Abstract: The present invention relates to a method for preparing piperidine derivative compounds by converting, with a piperidine compound, regioisomers having the formula: and where m is an integer from 1 to 6; Q and Y are the same or different and are selected from the group consisting of O, S, and NR5; G1, G2, and G3 are the same or different and are selected from the group consisting of OR8, SR8, and NR8R9; R6 and R7 are the same or different and are selected from the group consisting of hydrogen, an alkyl moiety, an aryl moiety, OR8, SR8, and NR8R9; X3 is halogen, OR15, SR15, NR15R16, OSO2R15, or NHSO2R15; R5, R8, R9, R15, and R16 are the same or different and are selected from the group consisting of hydrogen, an alkyl moiety, and an aryl moiety; and A is a substituent of its ring and is selected from the group consisting of hydrogen, halogens, alkyl, hydroxy, alkoxy, and other substituents.Type: GrantFiled: December 21, 1995Date of Patent: March 13, 2001Assignee: Albany Molecular Research, Inc.Inventors: Thomas E. D'Ambra, Garry M. Pilling
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Patent number: 6172093Abstract: New pesticidal substituted biphenytoxazolines of the formula (I) in which A, B, X, m and n have the meanings stated in the description, and new intermediates therefor.Type: GrantFiled: August 4, 1995Date of Patent: January 9, 2001Assignees: Bayer Aktiengesellschaft, Yashima Chemical Industry Co., LTDInventors: Reinhard Lantzsch, Albrecht Marhold, Wolfgang Kr{umlaut over (a)}mer, Christoph Erdelen, Ulrike Wachendorff-Neumann, Andreas Turberg, Norbert Mencke
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Patent number: 6165944Abstract: 4-(3-Heterocyclyl-1-benzoyl)pyrazoles of the formula I ##STR1## where: R.sup.1 and R.sup.3 are each hydrogen, nitro, halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, aminosulfonyl, N-alkylaminosulfonyl, N,N-dialkyl)aminosulfonyl, N-alkylsulfonylamino, N-haloalkylsulfonylamino, N-alkyl-N-alkylsulfonylamino or N-alkyl-N-haloalkylsulfonylamino;R.sup.2 is a 5- or 6-membered heterocyclyl radical with or without substitution which comprises 1 to 4 identical or different hetero atoms from the following group: oxygen, sulfur or nitrogen;R.sup.4 is hydrogen, halogen or alkyl;R.sup.5 is substituted pyrazole which is attached in position 4;and agriculturally useful salts thereof; processes for preparing the 4-(3-heterocyclyl-1-benzoyl)pyrazoles; compositions comprising them; and the use of these derivatives or these compositions comprising them for controlling undesirable plants.Type: GrantFiled: June 16, 1998Date of Patent: December 26, 2000Assignee: BASF AktiengesellschaftInventors: Wolfgang von Deyn, Regina Luise Hill, Ernst Baumann, Stefan Engel, Guido Mayer, Joachim Rheinheimer, Matthias Witschel, Ulf Misslitz, Oliver Wagner, Martina Otten, Helmut Walter, Karl-Otto Westphalen
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Patent number: 6156748Abstract: This invention relates to novel phenyl oxazoles, thiazoles, oxazolines, oxadiazoles and benzoxazoles useful as neuro-protective agents.Type: GrantFiled: October 6, 1997Date of Patent: December 5, 2000Assignee: Eli Lilly and CompanyInventors: Jill Ann Panetta, John Kevin Shadle, Lawrence Joseph Heinz, Michael LeRoy Phillips, John Robert Rizzo, Benjamin Alan Anderson, John Allan Rieck, III, David Lee Varie
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Patent number: 6153754Abstract: The present invention relates to a method for preparing piperidine derivative compounds by converting, with a piperidine compound, regioisomers having the formula: ##STR1## where Z is --CG.sup.1 G.sup.2 G.sup.3, ##STR2## and where m is an integer from 1 to 6; Q and Y are the same or different and are selected from the group consisting of O, S, and NR.sup.5 ; G.sup.1, G.sup.2, and G.sup.3 are the same or different and are selected from the group consisting of OR.sup.8, SR.sup.8, and NR.sup.8 R.sup.9 ; and R.sup.5, R.sup.8, and R.sup.9 are the same or different and are selected from the group consisting of hydrogen, an alkyl moiety, and an aryl moiety.Type: GrantFiled: December 21, 1995Date of Patent: November 28, 2000Assignee: Albany Molecular Research, Inc.Inventors: Thomas E. D'Ambra, Garry M. Pilling
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Patent number: 6153759Abstract: Heterocyclic substituted benzoyl derivatives of the formula ##STR1## where Z is a 5-membered or 6-membered heterocyclic, saturated or unsaturated radical containing one to three hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen, useful as intermediates for herbicidal compounds.Type: GrantFiled: January 7, 1999Date of Patent: November 28, 2000Assignee: BASF AktiengesellschaftInventors: Wolfgang von Deyn, Regina Luise Hill, Uwe Kardorff, Stefan Engel, Martina Otten, Marcus Vossen, Peter Plath, Harald Rang, Albrecht Harreus, Franz Rohl, Helmut Walter, Karl-Otto Westphalen, Ulf Misslitz
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Patent number: 6147220Abstract: This invention provides a process for the preparation of a 5-methylene-1,3-oxazoline from an alkyl ketone by reacting the alkyl ketone with an acetylating agent and an acid catalyst in an appropriate solvent and at an appropriate temperature. The resulting 5-methylene-1,3-oxazoline can be chlorinated and subsequently hydrolyzed to form an .alpha.-chloroketone which is useful as a fungicide.Type: GrantFiled: May 15, 1998Date of Patent: November 14, 2000Assignee: Rohm and Haas CompanyInventors: Renee Caroline Roemmele, Heather Lynnette Rayle
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Patent number: 6107319Abstract: Compounds of Formula I, and their agriculturally-suitable salts, are disclosed which are useful as arthropodicides ##STR1## wherein R.sup.1 -R.sup.5 and n are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula I and a method for controlling arthropods which involves contacting the arthropods or their environment with an effective amount of a compound of Formula I.Type: GrantFiled: July 15, 1998Date of Patent: August 22, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: Jeffrey Keith Long, Thomas Martin Stevenson
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Patent number: 6063932Abstract: Arthropodicidal oxazoline derivatives and processes and intermediates for the preparation thereof are disclosed. The intermediates are racemic or enantiomerically enriched compounds having formula (I), wherein R and n are disclosed in the specification.Type: GrantFiled: May 13, 1999Date of Patent: May 16, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: Gary David Annis, Rafael Shapiro
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Patent number: 6051589Abstract: The invention relates to novel diphenyloxazoline derivatives of the formula (I) ##STR1## in which a) A represents tri- to pentasubstituted phenyl andB represents substituted phenyl orb) A represents mono- or disubstituted phenyl andB represents at least trisubstituted phenyl, but where at least one substituent is not fluorine, chlorine, bromine, C.sub.1 -C.sub.6 -alkyl or -alkoxy,to a number of processes for their preparation and to their use as pest control agents.Type: GrantFiled: July 9, 1996Date of Patent: April 18, 2000Assignee: Bayer AktiengesellschaftInventors: Johannes Kanellakopulos, Gerd Kleefeld, Udo Kraatz, Ulrike Wachendorff-Neumann, Christoph Erdelen, Andreas Turberg, Norbert Mencke
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Patent number: 6031095Abstract: This invention relates to a highly selective process for preparation of E-.omega.-phenyl-.omega.-(3-pyridyl)-.omega.-alkenoic acid derivatives bearing a carbamoyl substituted oxazolyl or oxazolinyl group on the phenyl ring which demonstrate utility for thromboxane receptor antagonism and/or thromboxane synthase inhibition, as well as to intermediates therefor.Type: GrantFiled: September 10, 1998Date of Patent: February 29, 2000Assignee: Eli Lilly and CompanyInventors: Katrina Ann Nelson, Joseph John Nunes
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Patent number: 6028089Abstract: The invention relates to new phenylthio-oxazoline derivatives of the formula (I) ##STR1## in which A represents optionally substituted phenyl;B represents optionally substituted phenyl;D represents hydrogen or alkyl; andn represents 0, 1 or 2;to a plurality of processes for their preparation, and to their use as pesticides.Type: GrantFiled: February 25, 1998Date of Patent: February 22, 2000Assignee: Bayer AktiengesellschaftInventors: Wolfgang Kramer, Ulrike Wachendorff-Neumann, Christoph Erdelen, Andreas Turberg, Norbert Mencke
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Patent number: 5998575Abstract: A polymer alloy is obtained by adding a hydrophobic compound (1) having a hydrophobic main chain and a functional group containing an active hydrogen atom and a bisoxazoline compound (2) shown by the following formula to a composition containing plural polymers incompatible with each other: ##STR1## wherein D represents an optionally substituted alkylene group, cycloalkylene group or arylene group, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 respectively represent a hydrogen atom or an optionally substituted alkyl group or aryl group. The compound (1) includes a compound having an aliphatic hydrocarbon group as a main chain, containing a carboxyl group and having a molecular weight of 10,000 or less (e.g. higher fatty acids). A compatibilizing agent as produced by reacting the compound (1) and an excess amount of the compound (2) can also be used.Type: GrantFiled: May 9, 1996Date of Patent: December 7, 1999Assignee: KRI International, Inc.Inventors: Hajime Kambara, Tak Yuen Chow
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Patent number: 5994556Abstract: The present invention relates to optically pure bis(o-diarylphosphinophenyl)-tetrahydro-bi(1,3-oxazole) compounds represented by the formula (I) and a preparation method thereof. Bis(o-diarylphosphinophenyl)-tetrahydro-bi(1,3-oxazole) compounds of the present invention include (4S,4'S)-2,2'-bis(o-diarylphosphinophenyl)-4,4',5,5'-tetrahydro-4,4'-bi(1, 3-oxazole) represented by the formula (Ia) and its enantiomer, (4R,4'R)-2,2'-bis(o-diarylphosphinophenyl)-4,4',5,5'-tetrahydro-4,4'-bi(1, 3-oxazole) represented by the formula. The compounds of the present invention can be utilized in asymmetric hydrosilylation, hydrogenation, cyclopropylation and alkylation reactions.Type: GrantFiled: December 9, 1998Date of Patent: November 30, 1999Assignee: Korea Institute of Science and TechnologyInventors: Sang-Gi Lee, Choong-Eui Song, Chung-Woo Lim
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Patent number: 5994390Abstract: The present invention relates to therapeutically active compounds of formula I ##STR1## a method of preparing the same and to pharmaceutical compositions comprising the compounds. The novel compounds are useful in the prevention or treatment of estrogen related diseases or syndromes.Type: GrantFiled: October 27, 1997Date of Patent: November 30, 1999Assignee: Novo NordiskInventors: Poul Jacobsen, Svend Treppendahl, Paul Stanley Bury, Anders Kanstrup, Lise Brown Christiansen
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Patent number: 5990140Abstract: The invention relates to novel substituted oxazolines of the formula (I) ##STR1## in which A, B, D, E and G have the meaning given in the description,to a number of processes for their preparation and to their use as agents for combating pests.Type: GrantFiled: July 10, 1996Date of Patent: November 23, 1999Assignee: Bayer AktiengesellschaftInventors: Wolfgang Kramer, Reiner Fischer, Graham Holmwood, Hermann Hagemann, Ulrike Wachendorff-Neumann, Christoph Erdelen, Andreas Turberg, Norbert Mencke
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Patent number: 5990308Abstract: This invention relates to a highly selective process for preparation of E-.omega.-phenyl-.omega.-(3-pyridyl)-.omega.-alkenoic acid derivatives bearing a carbamoyl substituted oxazolyl or oxazolinyl group on the phenyl ring which demonstrate utility for thromboxane receptor antagonism and/or thromboxane synthase inhibition, as well as to intermediates therefore.Type: GrantFiled: September 10, 1998Date of Patent: November 23, 1999Assignee: Eli Lilly and CompanyInventors: Katrina Ann Nelson, Joseph John Nunes
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Patent number: 5977149Abstract: Cyclic amides of Formula (I) which are useful as fungicides wherein: A is O; S; N; NR.sup.5 ;or CR.sup.14--, G is C or N; W is O or S; X is OR.sup.1, S(O).sub.m R.sup.1 or halogen; R.sup.1, R.sup.2, and R.sup.5 are independently, in part, C.sub.1 -C.sub.6 alkyl; Y is, in part, --O--; --S(O).sub.n --,--CHR.sup.6 O--; or --CHR.sup.6 O--N.dbd.C(R.sup.7)--; Z is, in part, optionally substituted cycloalkyl, phenyl, pyridinyl, pyrimidinyl, or naphthyl; and R.sup.3, R.sup.4, R.sup.6, R.sup.7, R.sup.14, m, and n are defined in the disclosure, are disclosed.Type: GrantFiled: January 14, 1998Date of Patent: November 2, 1999Assignee: E. I. du Pont de Nemours and CompanyInventors: Richard James Brown, King-Mo Sun, Deborah Ann Frasier
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Patent number: 5973160Abstract: 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.Type: GrantFiled: February 13, 1996Date of Patent: October 26, 1999Inventors: Michael A. Poss, Jerome L. Moniot, Ivan D. Trifunovich, David J. Kucera, John K. Thottahil, Shu-Hui Chen, Jianmei Wei
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Patent number: 5969147Abstract: New pesticidal substituted biphenyloxazolines of the formula (I) in whichA, B, X, m and n have the meanings stated in the description, and new intermediates therefor.Type: GrantFiled: November 12, 1998Date of Patent: October 19, 1999Assignees: Bayer Aktiengesellschaft, Yashima Chemical Industry Co., LtdInventors: Reinhard Lantzsch, Albrecht Marhold, Wolfgang Kramer, Christoph Erdelen, Ulrike Wachendorff-Neumann, Andreas Turberg, Norbert Mencke
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Patent number: 5965579Abstract: The invention relates to compounds of the formula: ##STR1## Compounds of the above formula have a great affinity for the neurotensin receptors.Type: GrantFiled: November 21, 1997Date of Patent: October 12, 1999Assignee: SanofiInventors: Bernard Labeeuw, Danielle Gully, Francis Jeanjean, Jean-Charles Molimard, Robert Boigegrain
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Patent number: 5959114Abstract: This invention relates to a process for the preparation of an .alpha.-chloroketone compound comprising the steps of(i) cyclizing an alkynyl amide to form a 5-methyleneoxazoline ##STR1## (ii) chlorinating the 5-methyleneoxazoline using trichloroisocyanuric acid to produce a chlorinated oxazoline intermediate ##STR2## and (iii) hydrolyzing the chlorinated oxazoline intermediate with an aqueous acid to produce the desired monochloroketone ##STR3## wherein Z is alkyl or substituted alkyl, aryl or substituted aryl, heteroaryl or substituted heteroaryl or phenylene,R is a hydrogen atom or alkyl, andR.sup.1 and R.sup.2 are each independently an alkyl or substituted alkyl group, or R.sup.1 and R.sup.2 together with the carbon atom to which they are attached form a cyclic structure.Additionally, when R is a hydrogen atom, a dichloroketone can be conveniently formed through adjustment of reaction conditions.Type: GrantFiled: October 13, 1998Date of Patent: September 28, 1999Assignee: Rohm and Haas CompanyInventors: Heather Lynnette Rayle, Renee Caroline Roemmele, Randall Wayne Stephens
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Patent number: 5955491Abstract: The present invention provides a cathepsin L inhibitor containing a compound of the formula: ##STR1## wherein R.sup.1 is a hydrogen atom or an arylalkyl, heterocyclic-alkyl or lower alkyl group which may be substituted; R.sup.2 and R.sup.3 independently are a hydrogen atom or a hydrocarbon residue which may be substituted; R.sup.4 is an alkanoyl, sulfonyl, carbonyloxy, carbamoyl or thiocarbamoyl group which may be substituted; X is formula: --CHO or --CH.sub.2 OB (wherein B is a hydrogen atom or a protecting group of hydroxyl group); m and n independently are an integer of 0 or 1; provided that R.sup.4 is an alkanoyl group substituted by aryl, a sulfonyl group substituted by aryl having more than 9 carbon atoms or by lower alkyl, or a carbamoyl or thiocarbamoyl group which may be substituted when R.sup.1 is an unsubstituted lower alkyl, arylalkyl on methylthioethyl group, R.sup.2 and R.sup.3 independently are a lower alkyl or arylalkyl, X is --CHO, m is 1 and n is 0 or 1, or a salt thereof.Type: GrantFiled: June 27, 1995Date of Patent: September 21, 1999Assignee: Takeda Chemical Industries, Ltd.Inventors: Takashi Sohda, Yukio Fujisawa, Tsuneo Yasuma, Junji Mizoguchi, Masakuni Kori, Masayuki Takizawa
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Patent number: 5942621Abstract: This invention relates to a process for the preparation of an .alpha.-chloroketone compound comprising the steps of(i) cyclizing an alkynyl amide to form a 5-methyleneoxazoline ##STR1## (ii) chlorinating the 5-methyleneoxazoline using trichloroisocyanuric acid to produce a chlorinated oxazoline intermediate ##STR2## and (iii) hydrolyzing the chlorinated oxazoline intermediate with an aqueous acid to produce the desired monochloroketone ##STR3## wherein Z is alkyl or substituted alkyl, aryl or substituted aryl, heteroaryl or substituted heteroaryl or phenylene,R is a hydrogen atom or alkyl, andR.sup.1 and R.sup.2 are each independently an alkyl or substituted alkyl group, or R.sup.1 and R.sup.2 together with the carbon atom to which they are attached form a cyclic structure.Additionally, when R is a hydrogen atom, a dichloroketone can be conveniently formed through adjustment of reaction conditions.Type: GrantFiled: October 13, 1998Date of Patent: August 24, 1999Assignee: Rohm and Haas CompanyInventors: Heather Lynnette Rayle, Renee Caroline Roemmele, Randall Wayne Stephens
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Patent number: 5932738Abstract: This invention relates to a process for the preparation of an .alpha.-chloroketone compound comprising the steps of(i) cyclizing an alkynyl amide to form a 5-methyleneoxazoline ##STR1## (ii) chlorinating the 5-methyleneoxazoline using trichloroisocyanuric acid to produce a chlorinated oxazoline intermediate ##STR2## and (iii) hydrolyzing the chlorinated oxazoline intermediate with an aqueous acid to produce the desired monochloroketone ##STR3## wherein Z is alkyl or substituted alkyl, aryl or substituted aryl, heteroaryl or substituted heteroaryl or phenylene,R is a hydrogen atom or alkyl andR.sup.1 and R.sup.2 are each independently an alkyl or substituted alkyl group, or R.sup.1 and R.sup.2 together with the carbon atom to which they are attached form a cyclic structure.Additionally, when R is a hydrogen atom, a dichloroketone can be conveniently formed through adjustment of reaction conditions.Type: GrantFiled: October 13, 1998Date of Patent: August 3, 1999Assignee: Rohm and Haas CompanyInventors: Heather Lynnette Rayle, Renee Caroline Roemmele, Randall Wayne Stephens
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Patent number: 5863950Abstract: HIV protease inhibitors, obtainable by chemical synthesis, block the biological activity of the HIV protease enzyme, causing the replication of the HIV virus to terminate. These compounds, as well as pharmaceutical compositions that contain these compounds and possibly other anti-viral agents as ingredients, are thus suitable for the treatment of the HIV virus known to cause AIDS.Type: GrantFiled: October 27, 1994Date of Patent: January 26, 1999Assignee: Agouron Pharmaceuticals, Inc.Inventors: Siegfried H. Reich, Kathleen Lewis, Michael Melnick, Mary Ann M. Fuhry, Stephen Warren Kaldor
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Patent number: 5843972Abstract: The present invention relates to certain compounds of the formula (I) the racemic-enantiomeric mixtures and optical isomers of said compounds and the pharmaceutically acceptable salts or prodrugs thereof, depicted below, which are .beta.-adrenergic receptor agonists and accordingly have utility as, inter alia, hypoglycemic and antiobesity agents. More specifically, the compounds of the instant invention are selective agonists of .beta..sub.3 -adrenergic receptor. The invention also relates to methods of use for the compounds and to pharmaceutical compositions containing them. The compounds of the present invention also possess utility for increasing lean meat deposition and/or improving the lean meat to fat ratio in animals, e.g., ungulate animals, companion animals and poultry. The compounds have the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, Y and Z are as defined in the specification.Type: GrantFiled: March 28, 1997Date of Patent: December 1, 1998Assignee: Pfizer Inc.Inventors: Robert L. Dow, Stephen W. Wright
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Patent number: 5824677Abstract: Disclosed are compounds having a straight or branched aliphatic hydrocarbon structure of formula I: ##STR1## In formula I, n is an integer from one to four and m is an integer from four to twenty. Independently, R.sub.1 and R.sub.2 are hydrogen, a straight or branched chain alkyl, alkenyl or alkynyl of up to twenty carbon atoms in length or --(CH.sub.2).sub.w R.sub.5. If R.sub.1 or R.sub.2 is --(CH.sub.2).sub.w R.sub.5, w may be an integer from one to twenty and R.sub.5 may be an hydroxyl, halo, C.sub.1-8 alkoxyl group or a substituted or unsubstituted carbocycle or heterocycle. Alternatively, R.sub.1 and R.sub.2 may jointly form a substituted or unsubstituted, saturated or unsaturated heterocycle having from four to eight carbon atoms, N being a hetero atom of the resulting heterocyle. R.sub.3 may be either hydrogen or C.sub.13. In the compounds, a total sum of carbon atoms comprising R.sub.1 or R.sub.2, (CH.sub.2).sub.n and (CH.sub.2).sub.m does not exceed forty. R.sub.Type: GrantFiled: June 7, 1995Date of Patent: October 20, 1998Assignee: Cell Therapeutics, Inc.Inventors: J. Peter Klein, Gail E. Underiner, Anil M. Kumar
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Patent number: 5807877Abstract: The invention relates to new substituted biphenyloxazolines of the formula (I) ##STR1## in which R.sup.1 represents C.sub.1 -C.sub.6 -halogenoalkylthio andR.sup.2 represents hydrogen, orR.sup.1 and R.sup.2 together with the carbon atoms to which they are bonded form a halogen-substituted 5- or 6-membered heterocyclic ring,X represents hydrogen, halogen, C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.Type: GrantFiled: March 31, 1997Date of Patent: September 15, 1998Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Albrecht Marhold, Christoph Erdelen
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Patent number: 5808102Abstract: 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.Type: GrantFiled: August 22, 1997Date of Patent: September 15, 1998Assignee: Bristol-Myers Squibb CompanyInventors: Michael A. Poss, Jerome L. Moniot, Ivan D. Trifunovich, David J. Kucera, John K. Thottahil, Shu-Hui Chen, Jianmei Wei
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Patent number: 5801247Abstract: The present invention relates to processes for the enantioselective synthesis of hydroxypyrrolidines from amino acids. An amino methyl ester is used as the starting material. The ester is reacted with a benziminoethyl ether to produce an oxazoline or thiazoline. Specifically, L-serine methyl ester is used to produce 4-(carbomethoxy)-2-phenyl-.increment..sup.2 -oxazoline, and cysteine is used to produce the corresponding thiazoline. The oxazoline (or thiazoline) can be reduced to an aldehyde by treatment with a slight excess of DIBAL-H. The oxazoline is quenched with alcohol and reacted with (carbomethoxymethylene)triphenylphosphorane, to produce (S)-(+)-methyl (E)- and (S)-(-)-methyl (Z)-3-(4,5-dihydro-2-phenyl-4-oxazolyl)-2-propenoate. The double bond is hydroxylated to yield the diol esters. The resulting diol is then treated with aqueous acid to hydrolyze the oxazoline and recyclize to produce 3,4-dihydroxy-5-hydroxymethylpyrrolidone benzoate.Type: GrantFiled: January 23, 1997Date of Patent: September 1, 1998Assignee: Temple University-of the Commonwealth System of Higher EducationInventors: David R. Dalton, Yifang Huang
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Patent number: 5780497Abstract: The present invention relates to new 2-Phenyl-1-?4-(amino-1-yl-alk-1-ynyl)benzyl!-1H-indol-5-ol compounds which are useful as estrogenic agents, as well as pharmaceutical compositions and methods of treatment utilizing these compounds, which have the general structure below.Type: GrantFiled: April 14, 1997Date of Patent: July 14, 1998Assignee: American Home Products CorporationInventors: Chris P. Miller, Michael D. Collini, Bach D. Tran
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Patent number: 5739350Abstract: This invention provides some new synthetically obtained compounds of formula I and II ##STR1## which are useful as chemical intermediates. Representative formula I or II compounds have also been shown to possess useful ranges of antitumor activity in standard laboratory animal tests.In addition, the compounds of formula I or II can be linked to monoclonal antibodies, either directly or via known linking group, as a means of selectively delivering the CC-1065 analogs (Compounds of Formula I and II) to those target cells expressing the target antigen and thus selectively eliminating those diseased cells from the animal or human. Further, the compounds of formula I and II can be linked to soluble human CD4 or a soluble human CD4 protein fragment capable of binding to the gp120 envelope protein of the human immuno-virus and thus eliminate virally infected cells.Type: GrantFiled: June 7, 1995Date of Patent: April 14, 1998Assignee: Pharmacia & Upjohn CompanyInventors: Robert C. Kelly, Mark A. Mitchell, Paul A. Aristoff
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Patent number: 5718845Abstract: Nonlinear optical compounds which contain a heteroaromatic ring and may further comprise a tricyanovinyl group attached to the heteroaromatic ring.Type: GrantFiled: January 18, 1995Date of Patent: February 17, 1998Assignee: Enichem S.p.A.Inventors: Kevin J. Drost, Pushkara Rao Varanasi, Kwan-Yue Alex Jen, Michael Anthony Drzewinski
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Patent number: 5714518Abstract: HIV protease inhibitors, obtainable by chemical synthesis, block the biological activity of the HIV protease enzyme, causing the replication of the HIV virus to terminate. These compounds, as well as pharmaceutical compositions that contain these compounds and possibly other anti-vital agents as ingredients, are thus suitable for the treatment of the HIV virus known to cause AIDS.Type: GrantFiled: October 27, 1994Date of Patent: February 3, 1998Assignee: Agouron PharmaceuticalsInventors: Siegfried H. Reich, Mark J. Pino, Dzuy T. Nguyen, Anthony J. Trippe
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Patent number: 5705647Abstract: HIV protease inhibitors inhibit or block the biological activity of the HIV protease enzyme, causing the replication of the HIV virus to terminate. These compounds can be prepared by the novel methods of the present invention using the novel inventive intermediates.Type: GrantFiled: September 5, 1996Date of Patent: January 6, 1998Assignees: Agouron Pharmaceuticals, Inc., Japan Tobacco, Inc.Inventors: Srinivasan Babu, Bennett C. Borer, Travis P. Remarchuk, Robert J. Szendroi, Kathleen R. Whitten, Juliette K. Busse, Kim F. Albizati
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Patent number: 5659015Abstract: This invention relates to a method of producing peracetyloxazolines from peracetyl saccharides. The method involves reacting the starting material, a peracetyl saccharide, with a reagent combination, to directly produce the peracetyl oxazoline. This method may be used for the activation of oligosaccharides, wherein an oligosaccharide containing a reducing GlcNAc terminus is activated by the formation of an oxazolide at the terminal GlcNAc, and then coupled with a bifunctional spacer to provide an oligosaccharide-spacer conjugate. The activated oligosaccharide-spacer conjugate is then coupled to a protein, such as granulocyte colony stimulating factor or .gamma.-interferon, providing a neoglycoprotein conjugate. The invention provides a method for forming neoglycoprotein conjugates which may improve biological and physiochemical properties of the protein. For example, serum lifetime or efficiency of drug delivery of the peptide to a target organ or cell may be improved.Type: GrantFiled: October 13, 1992Date of Patent: August 19, 1997Inventors: Marcelo Colon, Jeffrey T. Davis, James R. Rasmussen, Marianne Borowski, Barbara Y. Wan, Shirish Hirani
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Patent number: 5639771Abstract: Disclosed are an oxazoline compound represented by the formula (I): ##STR1## wherein R.sup.1 represents halogen, hydrogen, alkyl, alkoxy, haloalkyl, haloalkoxy, phenyl, phenoxy, benzyl, benzyloxy, pyridyloxy, pyridylmethyloxy, alkoxy-substituted alkyl, nitro, cyanomethyloxy, haloalkylsulfonyloxy, alkylsulfonyloxy, or alkylthio; R.sup.2 represents hydrogen, halogen, alkyl, haloalkyl, alkoxy, alkylthio, or haloalkoxy; R.sup.1 and R.sup.2 may be combined to form a saturated or unsaturated 6-membered ring with oxygen; R.sup.3 represents hydrogen, halogen or alkoxy; R.sup.4 represents hydrogen, alkyl, or halogen; R.sup.5 represents hydrogen, halogen, or alkyl; X.sup.1 represents halogen, alkyl, haloalkyl, or alkoxy; X.sup.2 represents halogen, hydrogen, or alkoxy; X.sup.Type: GrantFiled: November 25, 1994Date of Patent: June 17, 1997Assignee: Ube Industries, Ltd.Inventors: Tokio Obata, Katsutoshi Fujii, Shoji Shikita, Kouichi Goka
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Patent number: 5635571Abstract: Polyoxazolines having the structural formula: ##STR1## wherein R is phenylene or alkylene containing 2 to 18 carbon atoms, R.sup.2 is C.sub.1-4 alkyl and R.sub.1 is selected from the group consisting of C.sub.1-12 alkyl, vinyl, isopropylidene, pentafluoroethyl, phenyl, hydroxyphenyl which is optionally interrupted by up to 20 ethylene oxide groups, C.sub.1-2 -alkoxyphenyl which is optionally interrupted by up to 20 ethylene oxide groups and .paren open-st.CH.sub.2 CH.sub.2 --O.paren close-st..sub.r CH.sub.3 in which r ranges from 1-20, X is NH.sub.2 or OH, n ranges from 2 to 50 and m ranges from 0 to 50, wherein R.sub.1 is hydroxyphenyl optionally interrupted by up to 20 ethylene oxide groups only when X is NH.sub.2, are polymerizable to form hyperbranched polymers which have a number average molecular weight ranging from 5,000 to 150,000, a weight average molecular weight ranging from 5,500 to 5,000,000 and a polydispersity ranging from 1.Type: GrantFiled: June 5, 1996Date of Patent: June 3, 1997Assignee: Cornell Research Foundation, Inc.Inventors: Jean M. J. Frechet, Koji Yui
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Patent number: 5633271Abstract: Arthropodicidally active compounds, compositions and a method for using them, the compounds having the formula ##STR1## wherein A, Q, Z, (E).sub.q, R.sup.1 and R.sup.2 are as defined in the text.Type: GrantFiled: January 16, 1996Date of Patent: May 27, 1997Assignee: E. I. Du Pont de Nemours and CompanyInventors: Victor E. Amoo, George P. Lahm, Thomas M. Stevenson
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Patent number: 5625067Abstract: The invention relates to cyclopentane ether derivatives of Formula I ##STR1## their salts with physiologically compatible bases, as well as the .alpha.-, .beta.- or .gamma.-cyclodextrin clathrates, and also the liposome-encapsulated compounds of Formula I, processes for their production, and their pharmaceutical usage.Type: GrantFiled: December 14, 1994Date of Patent: April 29, 1997Assignee: Schering AktiengesellschaftInventors: Hartmut Rehwinkel, Ulrich Klar, Helmut Vorbruggen, Karl-Heinz Thierauch, Peter Verhallen
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Patent number: 5621111Abstract: A process for the preparation of side chain-fluorinated alkyloxazoles, wherein hydroxyalkyloxazoles are reacted with an .alpha.,.alpha.-difluoroalkylamine at pressures of under 2 bar, in the presence of an inert solvent boiling at above 100.degree. C. (at normal pressure), and new fluorinated alkyloxazoles.Type: GrantFiled: October 17, 1995Date of Patent: April 15, 1997Assignee: Bayer AktiengesellschaftInventors: Norbert Lui, Albrecht Marhold
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Patent number: 5576443Abstract: Disclosed is a novel near-infrared absorbing dye of formula: ##STR1## wherein X.sup.1, X.sup.2 independently represents --CR.sup.8 R.sup.9 --, --S--, --Se--, --NR.sup.10 --, --CH.dbd.CH-- or --O--;n is an integer of 2 or 3;R.sup.1 and R.sup.2 independently represent alkyl of 1 to 10 carbons or substituted alkyl of 1 to 10 carbons;R.sup.3 represents a ring chosen from a set consisting of aryl, substituted aryl, and a heterocyclic ring of a type present in photographic emulsions;R.sup.4, R.sup.5, R.sup.6 and R.sup.7 independently represent hydrogen, alkyl of 1-10 carbons, substituted alkyl of 1-10 carbons, R.sup.4 and R.sup.5 taken together or R.sup.6 and R.sup.7 taken together can represent atoms necessary to form a 5 or 6-membered aliphatic ring, an aromatic six-membered ring, an aromatic 10-membered ring, a substituted aromatic six-member ring or a substituted aromatic 10-member ring;R.sup.8, R.sup.Type: GrantFiled: March 30, 1995Date of Patent: November 19, 1996Assignee: Sterling Diagnostic Imaging, Inc.Inventors: Dietrich M. Fabricius, Gregory C. Weed
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Patent number: 5567844Abstract: Replacement with fluorine of the primary hydroxy group of 1-phenyl-2-amino-1,3-propanediol compounds wherein the secondary hydroxy group and the amino group have been suitably protected.The reaction is carried out with an inorganic fluoride in a polyglycol.New oxazoline compounds particularly useful in said process.Type: GrantFiled: May 10, 1994Date of Patent: October 22, 1996Assignee: Zambon S.p.A.Inventors: Giancarlo Jommi, Dario Chiarino, Roberto Pagliarin
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Patent number: 5567717Abstract: A compound of the formula ##STR1## wherein Y, R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are as defined in the specification.Type: GrantFiled: June 5, 1995Date of Patent: October 22, 1996Assignee: Sterling Winthrop, Inc.Inventors: David J. Aldous, Thomas R. Bailey, Guy D. Diana, Theodore J. Nitz