Acyclic Carbon Bonded Directly To The -c(=x)- (e.g., N-oleoylpyrrolidine, Etc.) Patents (Class 548/540)
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Patent number: 6057456Abstract: The present invention is directed to a process for preparing alpha-arylated carbonyl-containing compounds, comprising the steps of reacting a compound having at least one carbonyl group with an arylating compound in the presence of a base and a transition metal catalyst under reaction conditions effective to form an alpha-arylated carbonyl-containing compound, the transition metal catalyst comprising a Group 8 metal and at least one chelating ligand selected from the group consisting of unsaturated Group 15 heterocycles, Group 15-substituted metallocenes, Group 15-substituted alkanes, Group 15-substituted arylenes, and combinations thereof. The process of the present invention simplifies the preparation of commercially significant organic alpha-aryl carbonyl-containing compounds, particularly for use in the pharmaceutical and polymer industries.Type: GrantFiled: October 15, 1998Date of Patent: May 2, 2000Assignee: Yale UniversityInventors: John F. Hartwig, Blake C. Hamann
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Patent number: 6054457Abstract: This invention relates to new benzamide derivatives having a vasopressin antagonistic activity, etc, and represented by general formula (I): ##STR1## wherein R.sup.1 is aryl optionally substituted with lower alkoxy, etc., R.sup.2 is lower alkyl, etc.,R.sup.3 is hydrogen, etc.,R.sup.4 is lower alkoxy, etc.,R.sup.5 is hydrogen, etc.,A is NH, etc.,E is ##STR2## etc., X is --CH.dbd.CH--, --CH.dbd.N--, or S, andY is CH or N,and pharmaceutically acceptable salts thereof, to processes for preparation thereof and to a pharmaceutical composition comprising the same.Type: GrantFiled: December 9, 1997Date of Patent: April 25, 2000Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Hiroyuki Setoi, Takehiko Ohkawa, Tatsuya Zenkoh, Hitoshi Sawada, Kentaro Sato, Hirokazu Tanaka
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Patent number: 6046192Abstract: The present invention relates to a phenylethanolaminotetralincarboxamide derivative represented by the general formula: ##STR1## (wherein A represents a lower alkylene group; B represents an amino group, a di(lower alkyl)amino group or a 3 to 7-membered alicyclic amino group which may contain an oxygen atom in the ring; the carbon atom marked with * represents a carbon atom in (R) configuration, (S) configuration or a mixture thereof; and the carbon atom marked with (S) represents a carbon atom in (S) configuration) and a pharmaceutically acceptable salt thereof, which have a selective .beta..sub.2 -adrenergic receptor stimulating effect with relieved burdens on the heart such as tachycardia and are useful as an agent for the prevention of threatened abortion and premature labor, a bronchodilator, and an agent for pain remission and promoting stone removal in urolithiasis.Type: GrantFiled: March 8, 1999Date of Patent: April 4, 2000Assignee: Kissei Pharmaceutical Co., Ltd.Inventors: Makio Kitazawa, Kosuke Okazaki, Tetsuro Tamai, Masaru Saito, Nobuyuki Tanaka, Hiroaki Kobayashi, Ken Kikuchi, Hideyuki Muranaka
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Patent number: 6037363Abstract: The present invention relates to pyrrolidine derivative compounds, and more particularly to the compound (S)-1-[(S)-2-(4-methoxybenzamido)-3-methylbutyryl]-N-[(S)-2-methyl-1-(trif luoroacetyl)propyl]pyrrolidine-2-carboxamide, shown by the formula I, a pharmaceutical composition comprising this compound in a crystalline form and a process for preparing the pharmaceutical composition. The compound of formula I is an inhibitor of human neutrophil elastase and is useful in the treatment of diseases in which the enzyme is implicated, such as, for example, emphysema and acute respiratory distress syndrome (ARDS).Type: GrantFiled: February 22, 1999Date of Patent: March 14, 2000Assignee: Zeneca LimitedInventors: Stephen John Pegg, George Joseph Sependa, Elwyn Peter Davies, Chris Allan Veale
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Patent number: 6034253Abstract: There is provided a process for the preparation of 5-(alkoxymethyl)-2,3-pyridinedicarboximide compounds having the structural formula I ##STR1## The 5-(alkoxymethyl)-2,3-pyridinedicarboximide compounds are useful as intermediates in the preparation of herbicidal 5-(alkoxymethyl)-2-(2-imidazolin-2-yl)-nicotinic acid, ester and salt compounds.Type: GrantFiled: January 22, 1999Date of Patent: March 7, 2000Assignee: America Cyanamid CompanyInventors: Kenneth Alfred Martin Kremer, Wen-Xue Wu, Donald Roy Maulding, deceased
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Patent number: 6028192Abstract: The present invention relates to a process for the preparation of compounds of the formula 1 ##STR1## by reacting a secondary acid amide of the formula 2 ##STR2## with an acid chloride of the formula 3 ##STR3## in the presence of N,N-diisopropyl-N-ethylamine. R.sup.1, R.sup.2 and R.sup.3 are alkyl or alkenyl radicals, if required also aryl radicals. The compounds of the formula 1 are suitable for use as insecticides or bleach activators.Type: GrantFiled: January 27, 1998Date of Patent: February 22, 2000Assignee: Clariant GmbHInventors: Johannes Becherer, Klaus Delpy, Karl-Heinz Keil, Bernhard Mees
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Patent number: 6022873Abstract: Compounds of formula (I) ##STR1## wherein n, V, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined in the specification are matrix metalloproteinase inhibitors.Type: GrantFiled: July 23, 1998Date of Patent: February 8, 2000Assignee: British Biotech Pharmaceuticals LimitedInventors: Raymond Paul Beckett, Fionna Mitchell Martin, Andrew Miller, Richard Simon Todd, Mark Whittaker
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Patent number: 6011155Abstract: N-(N'-substituted glycyl)-2-cyanopyrrolidines of formula I ##STR1## Compounds of formula I inhibit DPP-IV (dipeptidyl-peptidase-IV) activity. They are therefore indicated for use as pharmaceuticals in inhibiting DPP-IV and in the treatment of conditions mediated by DPP-IV, such as non-insulin-dependent diabetes mellitus, arthritis, obesity, osteoporosis and further conditions of impaired glucose tolerance.Type: GrantFiled: October 31, 1997Date of Patent: January 4, 2000Assignee: Novartis AGInventor: Edwin Bernard Villhauer
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Patent number: 6004992Abstract: The present invention relates to novel fluorobutenyl aminocarboxylates of the formula (I)R--CO--O--CH.sub.2 --CH.sub.2 --CX.dbd.CF.sub.2 (I)in whichX represents hydrogen or halogen andR represents one of the groups ##STR1## (b) R.sup.3 --A--CO--NR.sup.4 --CR.sup.5 R.sup.6 -- or ##STR2## in which A, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each as defined in the description, to processes for their preparation and to their use for controlling animal pests.Type: GrantFiled: May 22, 1998Date of Patent: December 21, 1999Assignee: Bayer AktiengesellschaftInventors: Udo Kraatz, Wolfram Andersch, Andreas Turberg, Norbert Mencke
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Patent number: 5994351Abstract: A compound of the formula ##STR1## wherein n, X, R.sup.3, R.sup.4 and Ar are as defined above, useful in the treatment of a condition selected from the group consisting of arthritis, cancer, tissue ulceration, restenosis, periodontal disease, epidermolysis bullosa, scleritis and other diseases characterized by matrix metalloproteinase activity, AIDS, sepsis, septic shock and other diseases involving the production of TNF.Type: GrantFiled: July 27, 1998Date of Patent: November 30, 1999Assignee: Pfizer Inc.Inventors: Ralph P. Robinson, James P. Rizzi
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Patent number: 5990131Abstract: This invention relates to neurotrophic low molecular weight, small molecule heterocyclic thioesters and ketones having an affinity for FKBP-type immunophilins, and their use as inhibitors of the enzyme activity associated with immunophilin proteins, particularly peptidyl-prolyl isomerase, or rotamase, enzyme activity.Type: GrantFiled: August 1, 1997Date of Patent: November 23, 1999Assignee: Gpi Nil Holdings Inc.Inventors: Gregory S. Hamilton, Jia-He Li
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Patent number: 5985911Abstract: C-terminal compounds of formula ##STR1## are potent inhibitors of matrix metalloproteinase and are useful in the treatment of diseases in which matrix metalloproteinase play a role. Also disclosed are matrix metalloproteinase inhibiting compositions and a method of inhibiting matrix metalloproteinase in a mammal.Type: GrantFiled: December 17, 1997Date of Patent: November 16, 1999Assignee: Abbott LaboratoriesInventors: Steven K. Davidsen, Alan S. Florjancic, George S. Sheppard, Jamie R. Giesler, Lianhong Xu, Yan Guo, Michael L. Curtin, Michael R. Michaelides, Carol K. Wada, James H. Holms
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Patent number: 5965612Abstract: 4-Cyano-4-deformylsordaricin derivatives are antifungal agents useful in the treatment and/or prevention of human and animal fungal infections, as well as in the control of phytopathogenic fungi in crops.Type: GrantFiled: July 28, 1998Date of Patent: October 12, 1999Assignee: Merck & Co., Inc.Inventor: Bruno Tse
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Patent number: 5965565Abstract: The present invention is directed to certain piperidines, pyrrolidines, and hexahydro-1H-azepines of the general structural formula: ##STR1## wherein B is selected from: ##STR2## and R.sup.1, R.sup.1a, R.sup.2a, R.sup.3a, R.sup.3b, R.sup.4, R.sup.4a, R.sup.4b, R.sup.4c, R.sup.5, D, X, Y, n, x and y are as defined herein. These compounds promote the release of growth hormone in humans and animals. This property can be utilized to promote the growth of food animals to render the production of edible meat products more efficient, and in humans, to treat physiological or medical conditions characterized by a deficiency in growth hormone secretion, such as short stature in growth hormone deficient children, and to treat medical conditions which are improved by the anabolic effects of growth hormone. Growth hormone releasing compositions containing such compounds as the active ingredient thereof are also disclosed.Type: GrantFiled: December 11, 1997Date of Patent: October 12, 1999Assignee: Merck & Co., Inc.Inventors: Meng H. Chen, Zhijian Lu, Ravi Nargund, Arthur A. Patchett, James R. Tata, Lihu Yang, Mu Tsu Wu
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Patent number: 5939437Abstract: Compounds of formula (I) and their pharmaceutically active salts are gastrin and CCK receptor ligands, where Ar is a monocyclic aromatic group, R.sup.1 is halo, amino, nitro, cyano, sulphamoyl, sulphonyl, trifluoromethyl, C.sub.1 to C.sub.3 alkyl, C.sub.1 to C.sub.3 alkylamino, C.sub.1 to C.sub.3 dialkylamino, phenyl, substituted phenyl, C.sub.1 to C.sub.3 alkoxy, hydroxy, esterified hydroxy, C.sub.1 to C.sub.3 hydroxyalkyl, C.sub.1 to C.sub.3 alkylcarboxyamino, carboxy, esterified carboxy and amidated carboxy, m is 0, 1, 2, 3, or 4, provided that m is not more than 2 unless R.sup.1 is exclusively halo, x+y=0 or 1, R.sup.2 and R.sup.4 independently are II, or C.sub.1 to C.sub.3 alkyl, R.sup.3 is H or C.sub.1 to C.sub.15 hydrocarbyl, where one or more hydrogen atoms of die hydrocarbyl group may be replaced by a halogen atom, and where up to two of the carbon atoms may be replaced by a nitrogen, oxygen or sulphur atom, provided that R.sup.3 does not contain a --O--O-- group, R.sup.5 is H or C.sub.1 to C.sub.Type: GrantFiled: December 20, 1996Date of Patent: August 17, 1999Assignee: James Black Foundation LimitedInventors: Sarkis Barret Kalindjian, Katherine Isobel Mary Steel, David John Dunstone, Ildiko Maria Buck
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Patent number: 5932745Abstract: This invention concerns the use of a hydroxylic solvent in the preparation of enaminones from the corresponding amine N-oxides or propargylic amines via the general process outlined below: ##STR1##Type: GrantFiled: June 30, 1998Date of Patent: August 3, 1999Assignee: American Home Products CorporationInventors: Russell G. Dushin, Eugene J. Trybulski
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Patent number: 5922863Abstract: Disclosed are ruthenium and osmium carbene compounds which are stable in the presence of a variety of functional groups and which can be used to catalyze olefin metathesis reactions on unstrained cyclic and acyclic olefins. Specifically, the present invention relates to carbene compounds of the formula ##STR1## wherein: M is Os or Ru; R and R.sup.1 are independently selected from hydrogen and functional groups C.sub.2 -C.sub.20 alkenyl, C.sub.2 -C.sub.20 alkynyl, C.sub.1 -C.sub.20 alkyl, aryl, C.sub.1 -C.sub.20 carboxylate, C.sub.2 -C.sub.20 alkoxy, C.sub.2 -C.sub.20 alkenyloxy, C.sub.2 -C.sub.20 alkynyloxy, aryloxy, C.sub.2 -C.sub.20 alkoxycarbonyl, C.sub.1 -C.sub.20 alkylthio, C.sub.1 -C.sub.20 alkylsulfonyl or C.sub.1 -C.sub.20 alkylsulfinyl; each optionally substituted with C.sub.1 -C.sub.5 alkyl, a halogen, C.sub.1 -C.sub.5 alkoxy or with a phenyl group optionally substituted with a halogen, C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkoxy; X and X.sup.Type: GrantFiled: October 26, 1995Date of Patent: July 13, 1999Assignee: California Institute of TechnologyInventors: Robert H. Grubbs, SonBinh T. Nguyen, Gregory C. Fu
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Patent number: 5919774Abstract: A class of novel pyrroles is disclosed together with the use of such compounds for inhibiting sPLA.sub.2 mediated release of fatty acids for treatment of conditions such as septic shock.Type: GrantFiled: December 5, 1997Date of Patent: July 6, 1999Assignee: Eli Lilly and CompanyInventors: Nicholas J. Bach, Robert D. Dillard, Susan E. Draheim
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Patent number: 5905166Abstract: A new type of yellow dyes with general formula Q-CO--CO--X is disclosed. They can be used in photographic materials as antihalation dyes, acutance dyes or filter dyes. Preferably they are incorporated in UV sensitive contact materials for pre-press applications.Type: GrantFiled: August 12, 1997Date of Patent: May 18, 1999Assignee: Agfa-Gevaert, N.V.Inventor: Eric Kiekens
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Patent number: 5874589Abstract: Disclosed are methods for synthesizing very large collections of diverse diverse tetramic acids, tetronic acids, pentamic acids, pentonic acids, and derivatives thereof and synthetic compound libraries comprising compounds prepared by such methods.Type: GrantFiled: July 18, 1997Date of Patent: February 23, 1999Assignee: Glaxo Wellcome, Inc.Inventors: David A. Campbell, Todd T. Romoff
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Patent number: 5859042Abstract: The instant invention is related to 5-membered heterocyclic compounds and pharmaceutical compositions which possess inhibitory activity on 5 alpha-reductase.Type: GrantFiled: March 13, 1997Date of Patent: January 12, 1999Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Sung Jai Lee, Takuya Seko, Manton Rodgers Frierson, Jagadish Chandra Sircar, Charles Xian Cao
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Patent number: 5852051Abstract: Compounds of the formula I ##STR1## in which R.sup.1, A and B have the meanings stated in the description, and the preparation thereof are described. The novel compounds are suitable for controlling diseases.Type: GrantFiled: June 5, 1997Date of Patent: December 22, 1998Assignee: BASF AktiengesellschaftInventors: Hans-Joachim Bohm, Stefan Koser, Helmut Mack, Thomas Pfeiffer, Werner Seitz, Hans Wolfgang Hoffken, Wilfried Hornberger, Thomas Zierke
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Patent number: 5847123Abstract: Imide compounds having a propioloyl group or pharmaceutically acceptable salts thereof which exhibit potent activities to inhibit the production of Interleukin 1-.beta. and also the production of Tumor Necrosis Factor .alpha.. These imide compounds are useful as a prophylactic or therapeutic agent for inhibiting the production of Interleukin 1-.beta. and the production of Tumor Necrosis Factor .alpha., typically for such diseases as chronic rheumatism, sepsis, ulcerative colitis, Crohn's disease and many other related diseases in which Interleukin 1-.beta. and/or Tumor Necrosis Factor .alpha. would participate.Type: GrantFiled: July 1, 1997Date of Patent: December 8, 1998Assignee: Nisshin Flour Milling Co., Ltd.Inventors: Shinji Yokoyama, Noriyoshi Sueda, Hiroaki Yamada, Ryotaro Kojima, Koichi Katsuyama
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Patent number: 5723470Abstract: Novel 3,4,4-trifluorobutenoic acid derivatives of the formula ##STR1## wherein Q is --(C.dbd.W)--R.sub.2 wherein W is O or S, and R.sub.2 is an aliphatic or aromatic group when W.dbd.O; --OR.sub.50 ; --SR.sub.50 ; or --NR.sub.50 R.sub.60 wherein R.sub.60 is hydrogen or R.sub.50 ; NR.sub.7 R.sub.8 ; a heterocyclic group; phenyl substituted by alkyl; or any agronomically acceptable salt thereof having usefulness as nematocides, insecticides and acaricides.Type: GrantFiled: February 12, 1996Date of Patent: March 3, 1998Assignee: Monsanto CompanyInventors: Dennis Paul Phillion, Peter Gerrard Ruminski, Gopichand Yalamanchili
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Patent number: 5708186Abstract: This invention relates to a method for the stereoselective synthesis of a 2-aryloxycarboxylic acid using a chiral auxiliary to enhance the stereoselectivity of the alkylation of the .alpha.-halo acid with an aryloxy group.Type: GrantFiled: December 6, 1996Date of Patent: January 13, 1998Inventors: Paul N. Devine, David M. Tschaen, Richard M. Heid, Jr.
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Patent number: 5703236Abstract: A compound represented by the formula I ##STR1## wherein X is independently both F or both Cl or one X is independently F and the other is independently Cl; R.sub.1 is a straight or branched chain (C.sub.3 to C.sub.8) alkyl group substituted by one or two hydroxy moieties, an ether ester (e.g., a polyetherester or phosphate ester) thereof or a pharmaceutically acceptable salt thereof and pharmaceutical compositions thereof useful for treating and/or preventing fungal infections are disclosed.Type: GrantFiled: June 2, 1995Date of Patent: December 30, 1997Assignee: Schering CorporationInventors: Anil K. Saksena, Viyyoor M. Girijavallabhan, Raymond G. Lovey, Russell E. Pike, Haiyan Wang, Yi-Tsung Liu, Ashit K. Ganguly, Frank Bennett
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Patent number: 5693310Abstract: Compounds of general Formula I ##STR1## wherein R.sup.3 is a saturated, unsaturated, straight- or branched-chain or cyclic aliphatic hydrocarbon residue of up to 16 carbon atoms or, if R.sup.4 is a hydrogen atom, a cycloalkyl group or an aryl or aralkyl group optionally substituted by one or several C.sub.1 -C.sub.6 -dialkylamino groups or by one or several C.sub.1 -C.sub.6 -alkoxy groups,R.sup.4 is a hydrogen atom, a saturated, unsaturated, straight- or branched-chain or cyclic hydrocarbon residue of up to 16 carbon atoms, orR.sup.3 and R.sup.4 jointly mean a saturated or unsaturated 5- or 6-membered ring optionally substituted or containing an O, S, N atom or oxo substituent, and Y is COOX or CONR.sub.3 R.sub.4,are valuable complexing agents, complexes or complex salts, e.g., for use as NMR or X-ray diagnostic image-enhancement agents or radioactive diagnostic agents.Type: GrantFiled: November 19, 1990Date of Patent: December 2, 1997Assignee: Schering AktiengesellschaftInventors: Heinz Gries, Bernd Raduechel, Hans-Joachim Weinmann, Wolfgang Muetzel, Ulrich Speck
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Patent number: 5693630Abstract: Compounds of the general formula ##STR1## or pharmaceutically acceptable salts thereof, wherein Z is a saturated or unsaturated 3 to 6 carbon chain,m is 2 or 3,R.sub.1 is a hydrogen atom, or a straight or branched C.sub.1-4 alkyl group,R.sub.2, R.sub.3 and R.sub.13 are situated in the ortho, meta, or para position of the phenyl ring and are the same or different and selected from the following groups: H, OH, OR.sub.14, halogen, CO.sub.2 R.sub.9, CN, CF.sub.3, NO.sub.2, NH.sub.2, COCH.sub.3,OSO.sub.2 CF.sub.3,OSO.sub.2 CH.sub.3,CONR.sub.10 R.sub.11, OCOR.sub.12, whereinR.sub.9, R.sub.12 and R.sub.14 is a straight or branched C.sub.1-4 alkyl group,R.sub.10 and R.sub.11 are the same or different and represents hydrogen or a straight or branched C.sub.1-6 alkyl group,R is 1) ##STR2## processes for their preparation, pharmaceutical preparations containing them and the use of the compounds in the treatment psychiatric disorders.Type: GrantFiled: October 26, 1994Date of Patent: December 2, 1997Assignee: Astra AktiebolagInventors: Stefan Bengtsson, Sven Hellberg, Nina Mohell, Lian Zhang, Gerd Hallnemo, David Jackson, Bengt Ulff
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Patent number: 5686435Abstract: The invention pertains to vitamin D amide derivatives of formula (I). These novel 1.alpha.-hydroxy vitamin D derivatives and their 20-epi analogues comprise compounds of formula (I) and corresponding 5,6-trans isomers, where Y represents an alkylene or alkenylene group containing up to four carbon atoms; R.sup.1 and R.sup.2 independently represent a hydrogen atom or a lower alkyl or cycloalkyl group, or R.sup.1 R.sup.2 N-- represents a heterocyclic group; and R.sup.3 and R.sup.4 independently represent a hydrogen atom or an O-protecting group. Active compounds, in which R.sup.3 and R.sup.4 are hydrogen atoms or metabolically labile O-protecting groups exhibit potent cell modulating effect, but minimal effect on calcium metabolism.Type: GrantFiled: December 7, 1995Date of Patent: November 11, 1997Assignee: Research Institute for Medicine and ChemistryInventors: Robert Henry Hesse, Gaddam Subba Reddy, Sundara Katugam Srinivasasetty Setty
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Patent number: 5676923Abstract: Diethylenetriaminepentaacetic acid monoamide derivatives, their complexes and complex salts, containing an element of atomic numbers 21-29, 31, 32, 39, 42-44, 49 or 57-83, pharmaceutical agents containing these compounds, their use as contrast media and process for their production.Type: GrantFiled: June 7, 1995Date of Patent: October 14, 1997Assignee: Schering AktiengesellschaftInventors: Johannes Platzek, Ulrich Niedballa, Peter Mareski, Bernd Raduchel, Hanns-Joachim Weinmann, Andreas Muhler, Bernd Misselwitz
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Patent number: 5674890Abstract: A compound of formula I ##STR1## in which Ar.sub.1 is naphthyl and phenyl, quinolyl or isoquinolyl optionally substituted; Ar.sub.2 is phenyl or thienyl optionally substituted; R.sub.1, R.sub.2 and R'.sub.2 are independently of each other H or (C.sub.1 -C.sub.4)alkyl or R.sub.1 represents a bond and N is covalently bonded to Ar.sub.2, and optionally R.sub.2 and R'.sub.2 form a double bond, or R.sub.1 or R.sub.2 is covalently bonded to Ar.sub.2 and represents a (C.sub.1 -C.sub.3 )alkylene; R.sub.3 and R.sub.4 are independently of each other H or (C.sub.1 -C.sub.4)alkyl or form, with the nitrogen atom to which they are attached pyrrolidine, ppiperidine, or hexahydroazepine; Z.sub.1 represents (C.sub.1 -C.sub.12)alkylene, optionally interrupted by a radical selected from the group consisting of (C.sub.5 -C.sub.7)cycloalkyl and phenyl or substituted with a radical selected from the group consisting of (C.sub.5 -C.sub.7)cycloalkyl and phenyl; Q.sub.1 is selected from the group consisting of methyl, amino, (C.sub.Type: GrantFiled: January 4, 1996Date of Patent: October 7, 1997Assignee: SanofiInventors: Bernard Christophe, Loic Foulon, Alain Pellet, Claudine Serradeil-Le Gal, Gerard Valette
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Patent number: 5661161Abstract: The present invention comprises analogs of the CAAX motif of the protein Ras that is modified by farnesylation in vivo. These CAAX analogs inhibit farnesyl-protein transferase. Furthermore, these CAAX analogues differ from those previously described as inhibitors of farnesyl-protein transferase in that they do not have a thiol moiety. The lack of the thiol offers unique advantages in terms of improved pharmacokinetic behavior in animals, prevention of thiol-dependent chemical reactions, such as rapid antoxidation and disulfide formation with endogenous thiols, and reduced systemic toxicity. Further contained in this invention are chemotherapeutic compositions containing these farnesyl transferase inhibitors and methods for their production.Type: GrantFiled: September 14, 1995Date of Patent: August 26, 1997Assignee: Merck & Co., Inc.Inventors: Neville J. Anthony, Terrence M. Ciccarone, S. Jane deSolms, Samuel L. Graham, Gerald E. Stokker, Catherine M. Wiscount
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Patent number: 5637730Abstract: A process for making pure sodium enalapril is provided which includes the step of decomplexing essentially pure sodium enalapril-sodium iodide complex to yield essentially pure sodium enalapril.Type: GrantFiled: August 19, 1996Date of Patent: June 10, 1997Assignee: Brantford Chemicals Inc.Inventors: K. S. Keshava Murthy, Andrew Burchat, Gamini Weeratunga
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Patent number: 5631385Abstract: Method for the preparation of N-protected 4-ketoproline derivatives of formula I ##STR1## by oxidation of the corresponding N-protected 4-hydroxyproline derivatives of ##STR2## using the system TEMPO (2,2,6,6-tetramethylpiperidinyl oxy free radical)/NaOCl.Type: GrantFiled: June 27, 1996Date of Patent: May 20, 1997Assignee: Degussa AktiengesellschaftInventors: Karlheinz Drauz, Matthias Kottenhahn, Klaus Stingl
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Patent number: 5624939Abstract: Compounds of formula I ##STR1## wherein the substituents are as defined herein, are disclosed as treatments for disorders linked to CCK and gastrin. Processes for preparing the compounds are also taught.Type: GrantFiled: June 28, 1995Date of Patent: April 29, 1997Assignee: Rhone-Poulenc Rorer, S.A.Inventors: Marc Capet, Marie-Christine Dubroeucq
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Patent number: 5622984Abstract: Amidinophenol derivatives of the formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are (i) H, (ii) C1-4 alkoxy, (iv) C2-5 acyl, (v) halogen, (vi) NO.sub.2, (vii) benzoyl, (viii) COOR.sup.4 (in which R.sup.4 is C1-3 alkyl); A is bond, C1-4 alkylene, --C(R.sup.5).dbd.C(R.sup.6)--(in which R.sup.5 and R.sup.6 are H or C1-4 alkyl; R.sup.3 is (i) CON(R.sup.7)(R.sup.8), (ii) CON(R.sup.9)--CH(R.sup.7)(R.sup.8) or (iii) ##STR2## in which R.sup.7 and R.sup.8 are (1) H,(2) phenyl, (3) C7-10 phenylalkyl, (4) phenyl or C7-10 phenylalkyl substituted by 1 or 2 C1-4 alkyl, halogen or R.sup.11 --COOR.sup.12 (in which R.sup.11 is bond, C1-8 alkylene, C2-8 alkenylene, C2-8 alkynylene; R.sup.12 is H, C1-4 alkyl, C7-10 phenylalkyl, phenyl, allyl, propargyl), (5) C1-10 alkyl, (6) C2-10 alkenyl having 1 to 3 double bonds, (7) C2-10 alkynyl having 1 or 2 triple bonds, (8) R.sup.11a --COXR.sup.12 (in which R.sup.Type: GrantFiled: March 1, 1995Date of Patent: April 22, 1997Assignee: Ono Pharmaceutical Company, LimitedInventors: Hisao Nakai, Masanori Kawamura, Tsumoru Miyamoto
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Patent number: 5605925Abstract: There are disclosed 1-aminoacetamidopyrroles and 1-amino-2-(substituted)pyrroles and related compounds of the formula ##STR1## wherein all substituents are defined herein, which are useful as glycine partial agonists and for the enhancement of learning and memory and for the treatment of memory dysfunctions associated with neurodegenerative disorders and are thus indicated in the treatment of Alzheimer's disease and other senile dementias.Type: GrantFiled: November 7, 1994Date of Patent: February 25, 1997Assignee: Hoechst Marion Roussel, Inc.Inventors: Lawrence L. Martin, Raymond W. Kosley, Jr., Denise M. Flanagan, Gert U. Kuerzel, Peter A. Nemoto, David G. Wettlaufer
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Patent number: 5594134Abstract: A process of synthesizing N-acyl auxiliary compounds is disclosed. A compound of the formula: ##STR1## is reacted with an anhydride in the presence of a lithium salt and an amine base to produce the N-acylated auxiliary.Type: GrantFiled: March 31, 1995Date of Patent: January 14, 1997Assignee: Merck & Co., Inc.Inventors: Guo-Jie Ho, David J. Mathre
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Patent number: 5576446Abstract: There are disclosed 1-aminoacetamidopyrroles and 1-amino-2-(substituted)pyrroles and related compounds of the formula ##STR1## wherein all substituents are defined herein, which are useful as glycine partial agonists and for the enhancement of learning and memory and for treatment of memory dysfunctions associated with neurodegenerative disorders and are thus indicated in the treatment of Alzheimer's disease and other senile dementias.Type: GrantFiled: November 7, 1994Date of Patent: November 19, 1996Assignee: Hoechst Marion Roussel, Inc.Inventors: Lawrence L. Martin, Raymond W. Kosley, Jr., Denise M. Flanagan, Gert U. Kuerzel, Peter A. Nemoto, David G. Wettlaufer
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Patent number: 5561146Abstract: Thrombin inhibitors are provided which have the formula ##STR1## wherein Z is a thrombin inhibitor substructure containing distal and proximal binding site residues; andR.sup.1 is cyano, hydroxyl, alkoxy, amino, aminoalkyl or nitro.Type: GrantFiled: October 14, 1994Date of Patent: October 1, 1996Assignee: Bristol-Myers Squibb CompanyInventors: Kyoung S. Kim, Spencer D. Kimball, Jagabandhu Das, Edwin J. Iwanowicz, Wen-Ching Han
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Patent number: 5545657Abstract: Heterocyclic compounds of the general formula: ##STR1## wherein, Z represents methylene group or sulfur atom, R represents a general formula:G--E--D--B--A--L represents a group of general formula:--CO--COR.sup.2--CO--R.sup.4--CO--CH.sub.2 --COR.sup.2--CO--CF.sub.2 --COR.sup.2--CO--CO--NR.sup.5 R.sup.6or--CO--CH.sub.2 --CO--NR.sup.5 R.sup.6and non-toxic salt or hydrate thereof possess an inhibitory activity on propyl endopeptidase, and therefore useful, for prevention and/or treatment of amnesia.Type: GrantFiled: December 9, 1994Date of Patent: August 13, 1996Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Masaaki Toda, Shuichi Ohuchida, Hiroyuki Ohno
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Patent number: 5514819Abstract: The present invention provides a dye-donor element for use according to thermal dye sublimation transfer, said dye-donor element comprising a support provided with a dye layer containing a dye and a polymeric binder, characterized in that said dye corresponds to the following formula: ##STR1## wherein R.sup.1 to R.sup.12 are as set out in the claims and the description.Type: GrantFiled: September 20, 1994Date of Patent: May 7, 1996Assignee: Agfa-Gevaert N.V.Inventor: Luc Vanmaele
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Patent number: 5510477Abstract: High quality acyl lactam imides are prepared by reacting an acyl lactam of the formula ##STR1## where 5 carbon atoms and an acylating acid of the formula R'CO.sub.2 H or by reacting a lactam, an anhydride of the formula (RCO).sub.2 O where R is 1 to 5 carbon atoms and an acylating acid, preferably in the presence of a base catalyst. The process affords acyl lactam imides in high yield and at lower reaction temperatures by providing for the removal of volatile carboxylic acid by-products under vacuum or by the use of a stripping gas. The acyl lactam imides are particularly suited for use as bleach activators in detergent compositions.Type: GrantFiled: March 1, 1994Date of Patent: April 23, 1996Assignee: The Procter & Gamble CompanyInventors: Alan D. Willey, Larry E. Miller
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Patent number: 5506258Abstract: The subject of the invention is the compounds of formula I ##STR1## in which Ar.sub.1 represents naphtyl, phenyl, quinolyl or isoquinolyl optionally substituted;Ar.sub.2 represents a phenyl or thienyl optionally substituted;R.sub.1, R.sub.2 and R'.sub.2 are independently of each other, H or (C.sub.1 -C.sub.4)alkyl;R.sub.1 represents nothing and N is attached to Ar.sub.2, and optionally R.sub.2 and R'.sub.2 form a double bond; or R.sub.1 or R.sub.2 is attached to Ar.sub.2 and represents a (C.sub.1 -C.sub.3)alkylene;R.sub.3 and R.sub.4, which are identical or different, represent H, (C.sub.1 -C.sub.4)alkyl or form, with the nitrogen atom to which they are attached, a (C.sub.5 -C.sub.7) saturated heterocycle selected from pyrrolidine, piperidine and hexahydroazepine;Z.sub.1 represents a (C.sub.1 -C.sub.12)alkylene, optionally interrupted or extended by a (C.sub.5 -C.sub.7)cycloalkyl or phenyl;Q.sub.1 represents methyl, amino, alkoxycarbonylamino, alkylamino, dialkylamino, a (C.sub.5 -C.sub.Type: GrantFiled: February 14, 1994Date of Patent: April 9, 1996Assignee: ELF SanofiInventors: Bernard Christophe, Loic Foulon, Alain Pellet, Claudine Serradeil-Le Gal, Gerard Valette
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Process for trans-6[2-(substituted-pyrrol-1-yl)alkyl]pyran-2-one inhibitors of cholesterol synthesis
Patent number: 5489690Abstract: An improved process for the preparation of trans-6-[2-(substituted-pyrrole-1-yl)alkyl]pyran-2-ones by a novel synthesis is described where .alpha.-metalated N,N-disubstituted acetamide is converted in seven operations to the desired products, and specifically, a process for preparing (2R-trans)-5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-[2-(tetrahy dro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1H-pyrrole-3-carboxamide, as well as other valuable intermediates used in the processes and prodrugs which are bioconverted to hypolipidemic and hypocholesterolemic agents and pharmaceutical compositions of the same.Type: GrantFiled: May 15, 1995Date of Patent: February 6, 1996Assignee: Warner-Lambert CompanyInventors: Donald E. Butler, Tung V. Le, Thomas N. Nanninga -
Patent number: 5484806Abstract: There are disclosed compounds of the formula: ##STR1## wherein R.sup.1 is hydrogen, alkyl, cycloalkyl, arylalkyl, --(CH.sub.2).sub.r CH.dbd.CH.sub.2, --(CH.sub.2).sub.s OY, --(CH.sub.2).sub.t CH(OZ)CH.sub.3, or Ar;X is O, S, or NR.sup.2 ;Y and Z are each, independently, hydrogen, alkyl, or --COR.sup.3 ;R.sup.2 and R.sup.3 are each, independently, hydrogen, alkyl, or arylalkyl;Ar is an aryl radical that may be optionally substituted;m=1-5;n=0-1;p=1-9;r=0-6;s=2-6; andt=0-6or a pharmaceutically acceptable salt thereof which are useful as antiinflammatory agents.Type: GrantFiled: May 8, 1995Date of Patent: January 16, 1996Assignee: American Home Products CorporationInventor: Dominic Mobilio
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Patent number: 5482961Abstract: New soft .beta.-adrenergic blocking agents, useful in the treatment or prevention of cardiovascular disorders and in the treatment of glaucoma, have the formula ##STR1## wherein n is an integer from 0 to 10; R is C.sub.6 -C.sub.12 cycloalkyl-C.sub.p H.sub.2p --, C.sub.6 -C.sub.18 polycycloalkyl-C.sub.p H.sub.2p --, C.sub.6 -C.sub.18 polycycloalkenyl-C.sub.p H.sub.2p -- or C.sub.6 -C.sub.12 cycloalkenyl-C.sub.p H.sub.2p -- (wherein p is 0, 1, 2 or 3), or together with the adjacent ##STR2## group represents a variety of other complex ester groupings; R.sub.1 is C.sub.1 -C.sub.7 alkyl; and Ar is a divalent radical containing at least one aromatic nucleus. The corresponding pharmaceutically acceptable acid addition salts are also described.Type: GrantFiled: May 6, 1994Date of Patent: January 9, 1996Inventor: Nicholas S. Bodor
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Patent number: 5475027Abstract: Urea-containing hydroxyethylamine compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease.Type: GrantFiled: November 8, 1993Date of Patent: December 12, 1995Assignee: G.D. Searle & Co.Inventors: John J. Talley, Daniel P. Getman, Ko-Chung Lin, Gary A. DeCrescenzo, Donald J. Rogier, Jr., John N. Freskos
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Patent number: 5464832Abstract: A thioacryloyl compound of the formula ##STR1## wherein Z is selected from the group consisting of OR, R and NR.sup.1 R.sup.2 ;R is selected from the group consisting of hydrogen; (C.sub.1 -C.sub.18)alkyl; (C.sub.1 -C.sub.8)alkenyl; (C.sub.1 -C.sub.8)haloalkynyl; 2-(5-chlorothienyl)methyl; phenyl optionally substituted with one or more substituents selected from the group consisting of halo-, (C.sub.1 -C.sub.3)alkoxy-, nitro-, and (C.sub.1 -C.sub.3)alkyl; phenacyl optionally substituted with one or more substituents selected from the group consisting of ring halo-, (C.sub.1 -C.sub.3)alkoxy-, nitro-, and (C.sub.1 -C.sub.3)alkyl; arylalkyl optionally substituted with one or more substituents selected from the group consisting of ring halo-, (C.sub.1 -C.sub.3)alkoxy-, nitro-, and (C.sub.1 -C.sub.3)alkyl;R.sup.1 and R.sup.2 are independently selected from (C.sub.1 -C.sub.8)alkyl and phenyl, or R.sup.1 and R.sup.Type: GrantFiled: December 13, 1993Date of Patent: November 7, 1995Assignee: Rohm and Haas CompanyInventors: Peter Osei-Gyimah, Samuel E. Sherba, Barry C. Lange, Rai J. Mehta, Rhoda W. Joseph
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Patent number: 5461071Abstract: A compound having the formula ##STR1## which is an anti-fungal agent is described. The producing organism Colletotricum accutatum is also described, along with a method of production.Type: GrantFiled: October 21, 1994Date of Patent: October 24, 1995Assignee: Merck & Co., Inc.Inventors: Evon A. Bolessa, Robert E. Schwartz, Gerald F. Bills, Robert A. Giacobbe, Fernando Pelaez Perez, Angeles Cabello Arroyo, Teresa Diez Matas, Isabel Martin Fernandez, Francisca Vincente Perez, Suzanne M. Mandala, Deborah L. Zink, Rosemary Thornton, John R. Thompson, James E. Curotto