The Carbonyl Is In A -coo- Group Patents (Class 546/318)
  • Patent number: 6165236
    Abstract: A poly(oxyalkylene)pyridyl or piperidyl ester having the formula: ##STR1## or a fuel-soluble salt thereof; wherein A is a nitrogen-containing ring selected from the group consisting of 3-pyridyl, 4-pyridyl, 3-piperidyl and 4-piperidyl; R.sub.1 and R.sub.2 are independently hydrogen or lower alkyl having 1 to about 6 carbon atoms and each R.sub.1 and R.sub.2 is independently selected in each --O--CHR.sub.1 --CHR.sub.2 -- unit; R.sub.3 is hydrogen, alkyl having 1 to about 100 carbon atoms, phenyl, aralkyl having about 7 to about 100 carbon atoms or alkaryl having about 7 to about 100 carbon atoms; x is an integer from 0 to 4; and n is an integer from about 5 to about 100.The poly(oxyalkylene)pyridyl and piperidyl esters of the present invention are useful as fuel additives for the prevention and control of engine deposits.
    Type: Grant
    Filed: June 2, 1999
    Date of Patent: December 26, 2000
    Assignee: Chevron Chemical Company LLC
    Inventor: Richard E. Cherpeck
  • Patent number: 6110970
    Abstract: This invention relates to nitrogen-containing oxyalkylene diester compositions for treating disease conditions including cancer and other proliferative diseases. The nitrogen-containing oxyalkylene diesters are represented by the formula ##STR1## where the nitrogen-containing group is R.sub.3 and includes particular alkyl, alkenyl, cycloalkyl, aryl, aralkyl, heterocycloalkyl or heteroaryl groups, which have nitrogen-containing substituents, such as amines, amides, or nitrogen heteroatoms.
    Type: Grant
    Filed: March 11, 1997
    Date of Patent: August 29, 2000
    Assignees: Beacon Laboratories, Inc., Mor Research Applications, Ltd., Bar-Ilan University
    Inventors: Abraham Nudelman, Ada Rephaeli
  • Patent number: 6090824
    Abstract: Compounds of formula I ##STR1## wherein Q.sup.1, Q.sup.2, Q.sup.3, and Q.sup.4 have any of the meanings given in the specification, their N-oxides, and their pharmaceutically acceptable salts are nonpeptide antagonists Substance P and NKA, useful for the treatment of asthma, etc. Also disclosed are pharmaceutical compositions, processes for preparing the compounds of formula I and intermediates.
    Type: Grant
    Filed: November 14, 1996
    Date of Patent: July 18, 2000
    Assignee: Zeneca Limited
    Inventors: Peter R. Bernstein, Bruce T. Dembofsky
  • Patent number: 6045720
    Abstract: A compound expressed by the following formula (1) and a liquid crystalline composition with using it are provided: ##STR1## wherein, either one of rings A, B and C denotes ##STR2## remaining two of them denote each independently ##STR3## R denotes an alkyl group or an alkoxy group with 4-16 carbon atoms, R* denotes ##STR4## in which, R.sub.1 denotes CH.sub.3, CF.sub.3, CH.sub.2 F or CHF.sub.2, R.sub.2 denotes an alkyl group with 1-10 carbon atoms and m denotes 2-12.The said compound exhibits a ferroelectric liquid crystalline phase and an antiferroelectric liquid crystalline phase by itself.
    Type: Grant
    Filed: December 4, 1998
    Date of Patent: April 4, 2000
    Assignee: Chisso Corporation
    Inventors: Ryushi Shundo, Shinichi Saito, Eiji Okabe, Hideo Saito
  • Patent number: 6022974
    Abstract: A process for the production of 2-chloro-5-chloromethylpyridine of the formula: ##STR1## starting from 6-hydroxynicotinic acid of the formula: ##STR2## In this way 6-hydroxynicotinic acid is reacted with an acid chloride to 6-hydroxynicotinoyl chloride of the formula: ##STR3## The latter is then catalytically hydrogenated with hydrogen to 6-hydroxy-5-hydroxymethylpyridine of the formula: ##STR4## The latter is then catalytically hydrogenated with hydrogen to 2-hydroxy-5-hydroxymethylpyridine of the formula: ##STR5## which is then chlorinated to the end product according to formula I.
    Type: Grant
    Filed: May 11, 1993
    Date of Patent: February 8, 2000
    Assignee: Lonza Ltd.
    Inventors: Oleg Werbitzky, Philipp Studer
  • Patent number: 5919792
    Abstract: 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: Grant
    Filed: October 28, 1997
    Date of Patent: July 6, 1999
    Assignee: Merck & Co., Inc.
    Inventors: Mark E. Duggan, George D. Hartman, William F. Hoffman, Nathan C. Ihle
  • Patent number: 5892050
    Abstract: There is provided a single vessel process for the preparation of a pyridine dicarboxylate compound of formula I ##STR1## via the sequential condensation of an alkyl vinyl ether with Vilsmeier reagent, oxalacetate and an ammonia source.
    Type: Grant
    Filed: January 28, 1998
    Date of Patent: April 6, 1999
    Assignee: American Cyanamid Company
    Inventor: Robert Francis Doehner, Jr.
  • Patent number: 5869676
    Abstract: The present invention relates to improved, efficient chemical syntheses of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP) and 3-amino-4-methylpyridine-2-carboxaldehyde thiosemicarbazone (3-AMP).
    Type: Grant
    Filed: May 15, 1997
    Date of Patent: February 9, 1999
    Assignee: Vion Pharmaceuticals, Inc.
    Inventors: ChuanSheng Niu, Jun Li, Xiuyan Li, Terrence W. Doyle, Shu-Hui Chen
  • Patent number: 5861419
    Abstract: The invention encompasses the novel compound of Formula I as well as a method of treating COX-2 mediated diseases comprising administration to a patient in need of such treatment of a non-toxic therapeutically effective amount of a compound of Formula I. ##STR1## The invention also encompasses certain pharmaceutical compositions for treatment of COX-2 mediated diseases comprising compounds of Formula I.
    Type: Grant
    Filed: July 11, 1997
    Date of Patent: January 19, 1999
    Assignee: Merck Frosst Canad, Inc.
    Inventors: Daniel Dube, Richard Friesen, Rejean Fortin, Zhaoyin Wang, Jacques Yves Gauthier
  • Patent number: 5747422
    Abstract: Substituted 2-phenylpyridines I ##STR1## where substituents have the meaning described in the specification and their use as herbicides; for the desiccation/defoliation of plants.
    Type: Grant
    Filed: July 3, 1997
    Date of Patent: May 5, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Schafer, Gerhard Hamprecht, Elisabeth Heistracher, Ralf Klintz, Hartmann Konig, Helmut Walter, Karl-Otto Westphalen, Ulf Misslitz
  • Patent number: 5739342
    Abstract: The present invention relates to an improved process for the preparation of nicotinic acids represented by the following structural formula (I): ##STR1## which are prepared by reacting a nicotinic amide compound having the formula: ##STR2## under acidic conditions with a nitrite salt. In the process of the invention have the groups R.sup.1, R.sup.2, and R.sup.3, in the compounds are independently selected from the group consisting of hydrogen, and halogen atoms and R.sup.4 is selected from the group consisting of hydrogen, lower alkyl and aryl. The process provides the nicotinic acid compounds in improved yields.
    Type: Grant
    Filed: March 3, 1997
    Date of Patent: April 14, 1998
    Assignee: Abbott Laboratories
    Inventors: Padam N. Sharma, Marazban H. Vandrevala
  • Patent number: 5716971
    Abstract: Pyridine derivatives of the formula ##STR1## wherein the ring A stands for an optionally further substituted benzene ring; the ring B stands for an optionally substituted pyridine ring; Q stands for hydroxyl group, or OQ.sup.1 or Q.sup.1 wherein Q.sup.1 stands for an optionally substituted aliphatic hydrocarbon group; and n denotes 0 or 1, or their salts, which have potassium.channel opening activity and are useful as therapeutic agents of circulatory diseases such as angina pectoris, hypertension, etc.
    Type: Grant
    Filed: August 9, 1996
    Date of Patent: February 10, 1998
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Mitsuru Shiraishi, Toshifumi Watanabe
  • Patent number: 5708175
    Abstract: A process for producing 4-trifluoromethylnicotinic acid of the formula (VIII) or its salt: ##STR1## which comprises (i) a first step of reacting a halide of the formula (I):CF.sub.3 COHal (I)wherein Hal is a halogen atom, with a compound of the formula (II):CH.sub.2 .dbd.CHOR.sup.1 (II)wherein R.sup.1 is an alkyl group, in the presence of a base to obtain a 4-alkoxy-1,1,1-trifluoro-3-buten-2-one of the formula (III):CF.sub.3 CO--CH.dbd.CH--OR.sup.1 (III)wherein R.sup.1 is as defined above, and reacting this compound with ammonia to obtain 4-amino-1,1,1-trifluoro-3-buten-2-one of the formula (IV): ##STR2## and (ii) a second step of subjecting the 4-amino-1,1,1-trifluoro-3-buten-2-one obtained in the first step and a compound of the formula (V):ACO.sub.2 R.sup.2 (V)wherein R.sup.2 is an ester-forming residue, and A is (R.sup.3 O)CH.dbd.CH-- or (R.sup.3 O).sub.2 CHCH.sub.2 --, wherein R.sup.
    Type: Grant
    Filed: May 16, 1996
    Date of Patent: January 13, 1998
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Toru Koyanagi, Tetsuo Yoneda, Fumio Kanamori, Shigehisa Kanbayashi, Toyoshi Tanimura, Noriyuki Horiuchi
  • Patent number: 5691366
    Abstract: A new nitro compound of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are each lower alkyl or lower alkoxy(lower)-alkyl, or ##STR2## is cyclized to form ##STR3## X is --O--, --S-- or --NH--, m is an integer 0 or 1, andR.sup.3 is carbamoyl, lower alkylcarbamoyl, lower alkanoyl, di-lower alkylaminosulfonyl, lower alkylsulfonyl, oxamoyl or a group of the formula: --(Y).sub.n --R.sup.4 wherein Y is --CO--, --SO.sub.2 --, --COCH.sub.2 -- or ##STR4## n is an integer of 0 or 1, and R.sup.4 is heterocyclic group which is optionally substituted with one or more substituents selected from lower alkyl, lower alkoxy, phenyl, carbamoyl, halogen, amino, lower alkylthio, hydroxy, lower alkylsulfonylamino and carbamoylmethyl, and pharmaceutically acceptable salt thereof, which are useful as vasodilators.
    Type: Grant
    Filed: October 31, 1995
    Date of Patent: November 25, 1997
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Masayuki Kato, Shigetaka Nishino, Mitsuko Hamano, Hisashi Takasugi
  • Patent number: 5659042
    Abstract: The present invention provides a method of preparation of ethyl 6-halonicotinate, wherein said halo is chloro or iodo, which comprises reacting the 6-halonicotinic acid with triethyl orthoacetate, to yield the ethyl-6-halonicotinate.
    Type: Grant
    Filed: October 25, 1994
    Date of Patent: August 19, 1997
    Assignee: Allergan
    Inventors: Samuel J. Gillett, Michael E. Garst, Alan T. Johnson
  • Patent number: 5605915
    Abstract: Compounds of the formula ##STR1## wherein the symbols have the meaning defined in the specification.
    Type: Grant
    Filed: May 31, 1996
    Date of Patent: February 25, 1997
    Assignee: Allergan
    Inventors: Vidyasagar Vuligonda, Richard L. Beard, Alan T. Johnson, Min Teng, Tae K. Song, Roshantha A. Chandraratna
  • Patent number: 5604227
    Abstract: The present invention relates to pyridazino[4,5-b]quinolines, and pharmaceutically useful salts thereof, which are excitatory amino acid antagonists and which are useful when such antagonism is desired such as in the treatment of neurological disorders. The invention further provides pharmaceutical compositions containing pyridazino[4,5-b]quinolines as active ingredient, and methods for the treatment of neurological disorders.
    Type: Grant
    Filed: April 13, 1995
    Date of Patent: February 18, 1997
    Assignee: Imperial Chemical Industries PLC
    Inventors: Thomas M. Bare, Richard B. Sparks
  • Patent number: 5599814
    Abstract: The present invention relates to pyridazino[4,5-b]quinolines, and pharmaceutically useful salts thereof, which are excitatory amino acid antagonists and which are useful when such antagonism is desired such as in the treatment of neurological disorders. The invention further provides pharmaceutical compositions containing pyridazino[4,5-b]quinolines as active ingredient, and methods for the treatment of neurological disorders.
    Type: Grant
    Filed: April 24, 1995
    Date of Patent: February 4, 1997
    Assignee: Imperial Chemical Industries, PLC
    Inventors: Thomas M. Bare, Richard B. Sparks
  • Patent number: 5591756
    Abstract: This invention relates to a compound of the formula: ##STR1## or a pharmaceutically acceptable salt thereof wherein X is oxygen, sulfur, --CH.dbd.CH--, or --CH.dbd.N--;wherein R.sup.1 is --CO.sub.2 R.sup.2 or tetrazole;wherein R.sup.2 is hydrogen, alkyl of 1 to 6 carbons or a pharmaceutically acceptable cation;wherein R is an alkyl of from 1 to 20 carbons, --(CH.sub.2).sub.p CF.sub.3 or --(CH.sub.2).sub.q R.sup.3 wherein R.sup.3 is alkoxy, phenoxy or alkoxy substituted phenoxy wherein the alkoxy group has from 1 to 8 carbons;wherein p and q are integers from 0 to 20;wherein n is 0 or 1; andwherein m is 0, 1, 2, or 3.
    Type: Grant
    Filed: May 19, 1995
    Date of Patent: January 7, 1997
    Assignee: G. D. Searle & Co.
    Inventors: Stevan W. Djuric, Richard A. Haack, Julie M. Miyashiro
  • Patent number: 5559134
    Abstract: The invention relates to leukotriene-B.sub.4 antagonists of formula I ##STR1## in which n represents a whole number from 2 to 5,X represents a direct bond, 1 to 6 methylene units, an ortho-, meta- or para-substituted phenyl ring or a meta- or para-substituted pyridine ring,Y represents a bond to a hydrogen atom and simultaneously to a hydroxy group, a double-bound oxygen atom or --O--CH.sub.2 --CH.sub.2 --O--,R.sub.1 and R.sub.2 represent the radical OH, --O--(C.sub.1 -C.sub.4)--alkyl, O--(C.sub.3 -C.sub.6)--cycloalkyl, --O--(C.sub.6 -C.sub.10)--aryl, --O--(C.sub.7 -C.sub.12)--aralkyl, O--(CH.sub.2)--CO-- (C.sub.6 -C.sub.10)--aryl or the radical NHR.sub.3 with R.sub.3 meaning hydrogen, (C.sub.1 -C.sub.4)--alkyl, (C.sub.3 -C.sub.6)--cycloalkyl or (C.sub.7 -C.sub.12)--aralkyl as well as their salts with physiologically compatible bases and their cyclodextrin clathrates.
    Type: Grant
    Filed: March 23, 1995
    Date of Patent: September 24, 1996
    Assignee: Schering Aktiengesellschaft
    Inventors: Bernd Buchmann, Werner Skuballa, Josef Heindl, Wolfgang Fr ohlich, Roland Ekerdt, Claudia Giesen
  • Patent number: 5534635
    Abstract: It has been found that pyridine-2-carboxamides of the formula ##STR1## wherein R is amino or a residue convertible into amino, and pharmaceutically usable acid addition salts of that carboxamide in which R is amino can be prepared in a simple manner and in good yield by reacting 2,5-dichloropyridine in the presence of a palladium-phosphine catalyst with an alkyne of the formulaR.sup.1 --C.tbd.CH IIIwherein R.sup.1 is hydrogen, lower-alkyl, trimethylsilyl or the group --(R.sup.2)(R.sup.3)--COH and R.sup.2 and R.sup.3 each independently are hydrogen or lower-alkyl or together are cyclopentyl or cyclohexyl,oxidizing the resulting alkyne to give 5-chloropyridine-2-carboxylic acid and reacting this acid or a reactive functional derivative thereof with an amino compound of the formulaor with carbon monoxide and an amino compound of formula VI or with carbon monoxide and a lower alkanol which is optionally mixed with water and reacting the resulting acid or the resulting ester with an amino compound of formula VI.
    Type: Grant
    Filed: September 12, 1994
    Date of Patent: July 9, 1996
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Michelangelo Scalone, Peter Vogt
  • Patent number: 5527921
    Abstract: Peroxycarboxylic ester photoinitiators derived from aromatic nitrogen containing heterocyclic carboxylic acids are described. The heterocyclic aromatic ring may contain additional nitrogen atoms, be fused with another aromatic ring system, be substituted with an additional peroxycarboxylic ester group and/or be substituted with an electron group having a Hammett sigma value greater than 0.1. The peroxycarboxylic ester photoinitiators have been found to be useful in photopolymerizable compositions and photosensitive elements.
    Type: Grant
    Filed: March 21, 1995
    Date of Patent: June 18, 1996
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Jeanne E. Haubrich
  • Patent number: 5520828
    Abstract: Novel fabric conditioners based on pyridine carboxylic acid esters or amides are described. The compounds are effective fabric conditioners and are biodegradable. Compositions including the compounds and a method of using the compositions are also described.
    Type: Grant
    Filed: January 30, 1995
    Date of Patent: May 28, 1996
    Assignee: Lever Brothers Company, Division of Conopco, Inc.
    Inventors: Shang-Ren Wu, Eddie N. Gutierrez
  • Patent number: 5508293
    Abstract: Disclosed are pyridinecarboximidamides having a vasodilating effect (hypotensive activity or antianginal activity), and acid adduct salts thereof. ##STR1## wherein when R.sup.1 represents an alkyl, hydroxyalkyl, carboxyl, amino, acylamino, alkylamino, dialkylamino, aralkylamino, alkylsulfonamide, bisalkylsulfonylamino or hydroxyl group, R.sup.2 represents a hydrogen atom and R.sup.3 represents a nitroxyl, 2-chlorophenyl or phenyl group; andwhen R.sup.1 represents a hydrogen atom, R.sup.2 represents an alkyl, hydroxyalkyl, carboxyl, amino, acylamino, alkylamino, dialkylamino, aralkylamino, alkylsulfonamide, bisalkylsulfonylamino or hydroxyl group and R.sup.3 represents a nitroxyl, 2-chlorophenyl or phenyl group.There is also disclosed the use of the compounds represented by the formula (I) for antihypertensive or antianginal purpose.
    Type: Grant
    Filed: September 27, 1994
    Date of Patent: April 16, 1996
    Assignee: Kirin Beer Kabushiki Kaisha
    Inventors: Hideki Okawara, Tatsuo Nakajima, Nobuyuki Ogawa, Tomoko Kashiwabara, Soichiro Kaneta
  • Patent number: 5502194
    Abstract: A process for the preparation of a 2-halogeno-pyridine of the formula ##STR1## in which X represents halogen andY represents halogen, nitro, formyl, cyano, carboxyl, carbamoyl, alkyl, halogenoalkyl, alkoxyalkyl, dialkoxyalkyl, alkoxycarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl,which comprises in a first stage reacting a pyridine 1-oxide of the formula ##STR2## with an organic nitrogen base A and an electrophilic compound, optionally in the presence of a diluent, to produce a compound of the formula ##STR3## in which A represents the radical of an organic nitrogen base, andZ.sup.- represents an anion formed from an electrophilic compound,optionally isolating and optionally purifying the compound of the formula (III).
    Type: Grant
    Filed: March 31, 1994
    Date of Patent: March 26, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Eric Rivadeneira, Klaus Jelich
  • Patent number: 5495023
    Abstract: A new nitro compound of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are each lower alkyl or lower alkoxy(lower)alkyl, or ##STR2## is cyclized to form ##STR3## X is --O--, --S-- or --NH--, m is an integer 0 or 1, andR.sup.3 is carbamoyl, lower alkylcarbamoyl, lower alkanoyl, di-lower alkylaminosulfonyl, lower alkylsulfonyl, oxamoyl or a group of the formula: --(Y).sub.n --R.sup.4whereinY is --CO--, --SO.sub.2 --, --COCH.sub.2 -- or ##STR4## n is an integer of 0 or 1, and R.sup.4 is heterocyclic group which is optionally substituted with one or more substituents selected from lower alkyl, lower alkoxy, phenyl, carbamoyl, halogen, amino, lower alkylthio, hydroxy, lower alkylsulfonylamino and carbamoylmethyl, and pharmaceutically acceptable salt thereof, which are useful as vasodilators.
    Type: Grant
    Filed: May 3, 1994
    Date of Patent: February 27, 1996
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Masayuki Kato, Shigetaka Nishino, Mitsuko Hamano, Hisashi Takasugi
  • Patent number: 5472687
    Abstract: Topical pyridine N-oxides, including 3-carboxypyridine N-oxide, niacinamide N-oxide, and .alpha.-(4-pyridyl-1-oxide)-N-t-butylnitrone, are disclosed. The topical compositions have utility in a topical pharmaceutical formulation for the cosmetic treatment of hair loss and the cosmetic stimulation of hair growth.
    Type: Grant
    Filed: February 7, 1994
    Date of Patent: December 5, 1995
    Inventor: Peter H. Proctor
  • Patent number: 5446057
    Abstract: Substituted tetrahydropyridines and piperidinecarboxylic acids and derivatives thereof are described, as well as methods for the preparation and pharmaceutical composition of same, which muscarinic antagonists are useful as agents for inhibiting gastric acid release, for treating bradycardia, bronchoconstriction, urinary incontinence, atonic conditions of the gut and bladder, Parkinson's disease, dystonias, and Alzheimer's disease.
    Type: Grant
    Filed: September 24, 1993
    Date of Patent: August 29, 1995
    Assignee: Warner-Lambert Company
    Inventors: Corinne E. Augelli-Szafran, Juan C. Jaen, Roy Schwarz, Anthony J. Thomas
  • Patent number: 5439925
    Abstract: Di(aromatic) compounds corresponding to the following formula: ##STR1## in which: Ar represents either ##STR2## n=1 or 2 or: ##STR3## X represents a divalent radical, Z represents O, S or a divalent radical, and R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 represent a hydrogen atom or various organic radicals, and the salts of the compounds of formula (I) when R.sub.1 is a carboxylic acid function. Use is in human and veterinary medicine and in cosmetics.
    Type: Grant
    Filed: December 16, 1993
    Date of Patent: August 8, 1995
    Assignee: Centre International de Recherches Dermatologiques Galderma (Cird Galderma)
    Inventors: Jean-Michel Bernardon, Willliam R. Pilgrim
  • Patent number: 5418245
    Abstract: Methods of inhibiting cell proliferation in a patient suffering from such disorder comprising the use of a styryl-substituted heteroaryl compound wherein the heteroaryl group is a monocyclic ring with 1 or 2 heteroatoms, or a bicyclic ring with 1 to about 4 heteroatoms, said compound optionally substituted or polysubstituted, with the proviso that when said ring is polysubstituted, the substituents do not have a common point of attachment to said ring, and those compounds wherein no substituent on the heteroaryl group is a carboxy group or an ester group, and pharmaceutical compositions comprising such compounds.
    Type: Grant
    Filed: March 17, 1994
    Date of Patent: May 23, 1995
    Assignee: Rhone-Poulenc Rorer International (Holdings) Inc.
    Inventors: Alfred P. Spada, Paul E. Persons
  • Patent number: 5401868
    Abstract: The present invention relates to hitherto unknown intermediate of formula, in which R.sub.1 stands for hydrogen or a straight or branched aliphatic C.sub.1 -C.sub.20 carbon chain or an aryl or aralkyl group, aryl and "ar" meaning an aromatic or heterocyclic, 5- or 6-membered ring substituent containing 1 or 2 hetero atoms selected among O, S and N, R.sup.1 optionally being further substituted, and its chain being interrupted by hetero atoms like oxygen, or by carbonyl group(s); and R.sup.3 stands for hydrogen or C.sub.1 -C.sub.3 alkyl. The present intermediates can be used in a one step method for producing prodrugs of formula, where D-H =drug itself.
    Type: Grant
    Filed: February 26, 1992
    Date of Patent: March 28, 1995
    Assignee: Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Productionsaktieselskab)
    Inventor: Frantz J. Lund
  • Patent number: 5393730
    Abstract: The invention relates to nicotinic acid hydrazone derivatives of formula I: ##STR1## in which the various symbols are as defined in the description, and their use as herbicides or as intermediates in the synthesis of herbicides.
    Type: Grant
    Filed: January 12, 1994
    Date of Patent: February 28, 1995
    Assignee: Rhone-Poulenc Agriculture Ltd.
    Inventor: Philip H. G. Smith
  • Patent number: 5387747
    Abstract: The present invention relates to the derivatives of the formula ##STR1## and their tautomeric forms, as well as their addition salts, and to their use in therapeutics, especially for the treatment and prevention of cardiovascular diseases and in particular for the treatment of hypertension, cardiac insufficiency and diseases of the arterial wall, especially atherosclerosis.
    Type: Grant
    Filed: April 16, 1993
    Date of Patent: February 7, 1995
    Assignee: Laboratoires Upsa
    Inventors: Nicole Bru-Magniez, Timur Gungor, Jean-Marie Teulon
  • Patent number: 5385920
    Abstract: Compounds of formula (I): ##STR1## in which: R.sub.1 and R.sub.2, which are identical or different, represent a higher alkyl or higher alkenyl radical,R.sub.3 represents a pyridyl or pyrazinyl radical,their isomers and their addition salts with a pharmaceutically acceptable acid and medicaments for the reduction of plasma lipids containing the same.
    Type: Grant
    Filed: June 9, 1993
    Date of Patent: January 31, 1995
    Assignee: Adir et Compagnie
    Inventors: Alex Cordi, Jean-Michel Lacoste, Jacques Duhault, Joseph Espinal, Michelle Boulanger
  • Patent number: 5374726
    Abstract: A process is provided for the preparation of 10-deazaaminopterins and 5,10- and 8,10-dideazaaminopterins starting from the corresponding homoterephthalic acid diester coupling the corresponding dicarboxylic acid diester having the formula: ##STR1## with the corresponding diaminopterin 6-methylene halide having the formula: ##STR2## thereby forming a pteroic acid diester having the formula: ##STR3## hydrolysing the two ester groups to form the corresponding carboxylic acid groups, and then monodecarboxylating the diacid, thereby removing the carboxylic acid group attached to the carbon alpha to the A group and forming a pteroic acid.
    Type: Grant
    Filed: March 9, 1993
    Date of Patent: December 20, 1994
    Inventors: Joseph I. DeGraw, William T. Colwell, James R. Piper
  • Patent number: 5336681
    Abstract: A derivative of general formula: ##STR1## wherein Y is --SO.sub.2 -- or ##STR2## (i) R.sup.1 and R.sup.2, which may the same or different, each represent, (1) --H, (2) C1-16 alkyl or (3) the formula: --X--A-- (R.sup.4)n wherein X is single-bond, --SO.sub.2 --, C1-4 alkylene, C1-4 alkylene substituted by --COOH or ##STR3## --A-- is a pyridyl or pyrrolyl ring, n is 1.about.5, R.sup.4 is 1 --H or C1-8 alkyl, 2 C1-14 alkoxy, 3 C1-6 alkylthio, 4 --OH, halogen, --NO.sub.2 or trihalomethyl, 5 the formula: --NR.sup.41 R.sup.42 wherein R.sup.41 and R.sup.42 each represents halogen or C1-4 alkyl, 6 tetrazole, 7 --SO.sub.3 H or --CH.sub.2 OH, 8 the formula: --SO.sub.2 NR.sup.41 R.sup.42 9 the formula: --Z.sup.41 --COOR.sup.43 wherein Z.sup.41 is single-bond, C1-4 alkylene or C2-4 alkenylene, R.sup.
    Type: Grant
    Filed: October 13, 1992
    Date of Patent: August 9, 1994
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Katsuhiro Imaki, Yoshinobu Arai, Tadao Okegawa
  • Patent number: 5324840
    Abstract: Compounds that provide non-teratogenic effects and lack irritation to the skin are shown in the formula below where the partially drawn ring signifies an aromatic ring which may be carbocyclic or heteroaromatic, 6-membered or 5-membered, and may be condensed with another ring. R.sub.1 is lower alkyl, Cl, Br, or I, R.sub.2 is H, lower alkyl, Cl, Br, or I, and R.sub.3 is lower alkyl, Cl, Br, I, or is an ether, thioether, ester, thioester, amine or substituted amine group.
    Type: Grant
    Filed: June 11, 1992
    Date of Patent: June 28, 1994
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. S. Chandraratna
  • Patent number: 5318994
    Abstract: Compounds of the formula: ##STR1## in which: A represents ##STR2## R represents linear or branched lower alkyl, R.sub.1 represents hydrogen or linear or branched lower alkyl, andR.sub.2 represents aryl or lower arylalkyl or aryl or lower arylalkyl substituted by lower alkyl, lower alkoxy, trifluoromethyl, or halogen, aryl means phenyl or naphthyl, as well as optical isomers, epimers and diastereoisomers and addition salts thereof with a pharmaceutically-acceptable acid, lower alkyl and lower alkoxy having 1 to 6 carbon atoms inclusive, andmedicaments containing the same which are useful for the treatment of disorders of the melatoninergic system.
    Type: Grant
    Filed: November 3, 1992
    Date of Patent: June 7, 1994
    Assignee: Adir et Compagnie
    Inventors: Jean Andrieux, Raymond Houssin, Said Yous, Beatrice Guardiola, Daniel Lesieur
  • Patent number: 5296601
    Abstract: A process for producing a carboxylic acid ester, which comprises reacting an organic chloride having at least one chlorine atom on its ring of a substituted or unsubstituted, aromatic or heterocyclic hydrocarbon with carbon monoxide and an amine or an alcohol in the presence of a base by using as catalysts a palladium compound and a phosphine compound represented by the general formula (V):(R).sub.2 P--X--P(R).sub.2 (V)wherein R is an alkyl group or a substituted or unsubstituted phenyl group, and X is an alkylene group having 1 to 6 carbon atoms, ##STR1## or a binaphthyl group.
    Type: Grant
    Filed: May 27, 1992
    Date of Patent: March 22, 1994
    Assignee: Nihon Nohyaku Co., Ltd.
    Inventors: Keiji Suto, Masaaki Kudo, Moriharu Yamamoto
  • Patent number: 5262387
    Abstract: Pyridine derivatives of the formulae ##STR1## wherein W, X, Y and Z are each C--R.sup.4, N or N.fwdarw.O, with the proviso that the ring contains only one heteroatom, and the substituents R.sup.1, R.sup.2 and R.sup.3 have the following meanings:R.sup.1 is alkoxy, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, or substituted or unsubstituted alkynyl,R.sup.2 is hydrogen,R.sup.3 is formyl, 4,5-dihydrooxazol-2-yl or --CO--A--R.sup.5 or --CO--NR.sup.6.sup.R.sup.7, whereR.sup.
    Type: Grant
    Filed: November 20, 1991
    Date of Patent: November 16, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerhard Hamprecht, Norbert Goetz, Bruno Wuerzer, Karl-Otto Westphalen
  • Patent number: 5260323
    Abstract: 2,4- and 2,5-substituted pyridine-N-oxides are provided which are effective as fibrosuppressives and immunosuppressives. Said compounds are also suitable for the treatment of disorders of the metabolism of collagen and collagen-like substances or the biosynthesis of Clq.
    Type: Grant
    Filed: November 19, 1992
    Date of Patent: November 9, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ekkehard Baader, Martin Bickel, Volkmar Gunzler-Pukall
  • Patent number: 5256678
    Abstract: This invention relates to n-pentadecyl nicotinate N-oxide, a hair restorer composition comprising said compound as the active ingredient and a method of hair restoring utilizing said compound.
    Type: Grant
    Filed: May 22, 1992
    Date of Patent: October 26, 1993
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventor: Osamu Nakaguchi
  • Patent number: 5250542
    Abstract: 3,4,4-trisubstitutedpiperidinyl-N-alkylcarboxylates and intermediates for their preparation are provided. These piperidine-N-alkylcarboxylates are useful as peripheral opioid antagonists.
    Type: Grant
    Filed: July 17, 1992
    Date of Patent: October 5, 1993
    Assignee: Eli Lilly and Company
    Inventors: Buddy E. Cantrell, Dennis M. Zimmerman
  • Patent number: 5245039
    Abstract: A process for the optical resolution of racemic 1,4-dihydropyridines, containing isothioureido groups. Salification of racemic isothioureas with optically active acids produces diasteroisomeric mixtures of isothiouronium salts, that, using conventional techniques, are separated in the individual components to give optically pure isothioureides of 1,4-dihydropyridines and salts thereof with conventional acids. Said optically pure 1,4-dihydropyridines can then be subjected to desulphuration and to different transformations to give to other enantiomerically pure and therapeutically useful 1,4-dihydropyridines.
    Type: Grant
    Filed: August 14, 1991
    Date of Patent: September 14, 1993
    Assignee: Boehringer Mannheim Italia
    Inventors: Carmelo A. Gandolfi, Marco Frigerio, Carlo Riva, Andrea Zaliani, Giorgio Long, Roberto D. Domenico
  • Patent number: 5238948
    Abstract: The invention relates to pyridine-2,4- and -2,5-dicarboxylic acid derivatives of the formula I ##STR1## in which R.sup.1, R.sup.2 and X have the meanings given, a process for the preparation of these compounds and their use, in particular in medicaments for influencing the metabolism of collagen and collagen-like substances or the biosynthesis of C1.sub.q.
    Type: Grant
    Filed: August 25, 1992
    Date of Patent: August 24, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Martin Bickel, Dietrich Brocks, Harald Burghard, Volkmar Gunzler, Stephan Henke, Hartmut Hanauske-Abel
  • Patent number: 5235060
    Abstract: The present invention relates to novel substituted pyridine compounds useful as intermediates in the preparation of herbicidal compounds and the process for the preparation of said pyridine compounds. ##STR1## wherein: R.sup.1 is selected from the group C.sub.1 -C.sub.4 alkyl;R.sup.2 is selected from the group hydrogen, C.sub.1 -C.sub.3 alkyl optionally substituted with methoxy or 1-3 fluorine and C.sub.1 -C.sub.2 alkoxy optionally substituted with 1-3 fluorine;R.sup.3 is selected from the group C.sub.1 -C.sub.3 alkyl substituted with methoxy or 1-3 fluorine;R.sup.4 is selected from the group SO.sub.2 R.sup.5, CO.sub.2 R.sup.5 and C(O)N(R.sup.6).sub.2 ;R.sup.5 is selected from the group C.sub.1 -C.sub.2 alkyl optionally substituted with C.sub.1 -C.sub.2 alkoxy or 1-3 halogens independently selected from the group chlorine and fluorine;R.sup.6 is C.sub.1 -C.sub.2 alkyl;M is selected from the group Li, Na, K, Mg, Ca, NH.sub.4, and alkyl substituted NH.sub.4.
    Type: Grant
    Filed: July 11, 1991
    Date of Patent: August 10, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Charles D. Adams, Greg A. Bullock, George C. Chiang
  • Patent number: 5216170
    Abstract: A compound for promoting livestock production and for controlling obesity in humans and animals, of the formula ##STR1## in which A represents .dbd.CH-- or .dbd.N--,R.sup.0 represents hydrogen or methyl,R.sup.1 and R.sup.3 each independently represents hydrogen, hydroxyl, halogen, cyano, alkyl, halogenoalkyl, hydroxyalkyl, alkoxycarbonyl, aminocarbonyl, mono- and dialkylaminocarbonyl, alkoxy, halogenoalkoxy, halogenoalkylthio, NHSO.sub.2 -alkyl,R.sup.2 represents hydrogen, hydroxyl, alkoxy or the radical --NR.sup.5 R.sup.6,R.sup.4 represents hydrogen, C.sub.1 -C.sub.10 -alkyl which is optionally substituted by hydroxyl, halogen, alkoxy, acyloxy or the radical --NR.sup.7 R.sup.8, or represents the radical COR.sup.9 or the radical --O--Z--R.sup.10,Z represents C.sub.1 -C.sub.10 -alkylene, -alkenylene or alkynylene,R.sup.5 represents hydrogen or alkyl,R.sup.6 represents hydrogen, alkyl, halogenoalkyl or acyl, or R.sup.5 and R.sup.
    Type: Grant
    Filed: March 28, 1991
    Date of Patent: June 1, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans Lindel, Werner Hallenbach, Friedrich Berschauer, Heinrich A. Greife, Gernot Klotz
  • Patent number: 5204478
    Abstract: An improved process for the preparation of 2,6-dichloro-5-fluoronicotinoyl chloride is described where a 2,6-dihydroxy-5-fluoronicotinic acid ester is converted in one step using phosphorus oxychloride and a lithium reagent to 2,6-dichloro-5-fluoronicotinoyl chloride and subsequent basic hydrolysis affords 2,6-dichloro-5-fluoronicotinic acid.
    Type: Grant
    Filed: August 20, 1992
    Date of Patent: April 20, 1993
    Assignee: Warner-Lambert Company
    Inventor: Rex A. Jennings
  • Patent number: 5198451
    Abstract: Novel N-substituted azaheterocyclic carboxylic acids and esters thereof in which a substituted alkyl chain forms part of the N-substituent, the compounds thus having the general formula I ##STR1## wherein Y is ##STR2## wherein R.sup.1 and R.sup.2 independently are C.sub.3-8 cycloalkyl phenyl or thienyl all of which may be optionally substituted with halogen, trifluoromethyl, C.sub.1-16 alkyl or C.sub.1-6 alkoxy;s is 1, 2 or 3;x is --CH.sub.2 --, --O-- or ##STR3## -wherein R.sup.3 is hydrogen or C.sub.1-6 -alkyl; r is 2, 3 or 4; R.sup.4 and R.sup.5 each represents hydrogen or may together represent a bond and R.sup.6 is OH or C.sub.1-8 -alkoxy; and pharmaceutically acceptable acid addition salts are potent inhibitors of GABA uptake from the synaptic cleft.
    Type: Grant
    Filed: November 20, 1990
    Date of Patent: March 30, 1993
    Assignee: Novo Nordisk A/S
    Inventors: Knud E. Andersen, Lars J. Stray Knudsen, Ursula Sonnewald, Per O. Sorensen
  • Patent number: 5196045
    Abstract: A compound having the structural formula ##STR1## wherein: Y is selected from O and S;R.sub.1 and R.sub.4 are independently selected from fluorinated methyl, chlorofluorinated methyl, and C.sub.1 -C.sub.4 alkyl, provided that not both R.sub.1 and R.sub.4 may be C.sub.1 -C.sub.4 alkyl;R.sub.2 is selected from hydrogen, lower alkyl, haloalkyl, alkenyl, alkynyl, haloalkenyl, and a cation;R.sub.3 is selected from C.sub.1 -C.sub.5 alkyl, cycloalkyl, cycloalkylalkyl, hydroxy, and alkoxy; andX is selected from ##STR2## in which R.sub.8 is selected from H, alkyl and CF.sub.3 and R.sub.10 is selected from F, Cl, --OR.sup.1, --SR.sup.1, --NHR.sup.1, --N(R.sup.1).sub.2, phenyl, substituted phenyl, and --P(OR.sup.1).sub.2where R.sup.1 is as defined above; ##STR3## wherein R.sup.1 is as defined above; ##STR4## wherein R.sub.14 and R.sub.15 are independently selected from hydrogen and alkyl; and --N.dbd.C.dbd.O and their use as herbicides.
    Type: Grant
    Filed: March 20, 1991
    Date of Patent: March 23, 1993
    Assignee: Monsanto Company
    Inventors: Len F. Lee, Mark G. Dolson