Acyclic Chalcogen Bonded Directly To Ring Carbon Of The Bicyclo Ring System Patents (Class 546/116)
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Patent number: 5350854Abstract: Novel 2-alkyl carbinol derivatives of deoxynojirimycin (DNJ) and the chemical synthesis of these derivatives and intermediates therefor from DNJ and their method of inhibiting lentiviruses are disclosed.Type: GrantFiled: July 12, 1993Date of Patent: September 27, 1994Assignee: G. D. Searle & Co.Inventors: Ish K. Khanna, Richard A. Mueller, Richard M. Weier
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Patent number: 5336771Abstract: The present invention relates to processes and intermediates for the preparation of spiro-heteroazolones. The latter compounds are useful as aldose reductase inhibitors.Type: GrantFiled: October 14, 1992Date of Patent: August 9, 1994Assignee: Pfizer Inc.Inventors: Charles W. Murtiashaw, George J. Quallich
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Patent number: 5334596Abstract: Fibrinogen receptor antagonists having the formula ##STR1## for example ##STR2##Type: GrantFiled: May 11, 1993Date of Patent: August 2, 1994Assignee: Merck & Co., Inc.Inventors: George D. Hartman, Wasyl Halczenko, John D. Prugh
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Patent number: 5334717Abstract: Novel derivatives of 1-deoxynojirimycin are disclosed which have amino or azido substituents at C-2 and/or C-3. These compounds are useful inhibitors of lentiviruses. Methods of chemical synthesis of these derivatives and intermediates therefor are also disclosed.Type: GrantFiled: January 8, 1993Date of Patent: August 2, 1994Assignee: G. D. Searle & Co.Inventors: Ish K. Khanna, Richard A. Mueller, Richard M. Weier
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Patent number: 5331096Abstract: Novel derivatives of 1-deoxynojirimycin are disclosed which have thio or sulfinyl substituents at C-2 or C-3. These compounds are useful inhibitors of lentiviruses such as visna virus and human immunodeficiency virus. Methods of chemical synthesis of these derivatives and intermediates therefor are also disclosed.Type: GrantFiled: August 2, 1993Date of Patent: July 19, 1994Assignee: G. D. Searle & Co.Inventors: Francis J. Koszyk, Richard A. Mueller
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Patent number: 5322944Abstract: Process for preparing enantiomers of general formula (I): ##STR1## where Z, R.sub.1, R.sub.2, R.sub.3 and n are defined in the description. The compounds obtained according to the invention are useful as medicinal products.Type: GrantFiled: June 30, 1992Date of Patent: June 21, 1994Assignee: Adir et CompagnieInventors: Gerald Guillaumet, Claude Fugier, Jean-Claude J. Souvie, Gerard Adam, Pierre Renard, Daniel-Henri Caignard
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Patent number: 5315007Abstract: Processes for making compounds of Formulae XIV, XV, and XVII ##STR1## wherein R.sub.6 is lower alkyl, R.sub.7 is lower alkyl, R is lower alkyl, Y is H, F or Cl, R.sub.8 is a compound of Formula XVIII ##STR2## wherein n is 1, 2, or 3, R.sub.11 is C.sub.1 -C.sub.4 alkyl and R.sub.12 is the same as R.sub.11, or R.sub.11 and R.sub.12 together form cyclopentane or cyclohexane, and R.sub.13 is:(a) phenyl substituted 1 to 5 times with C.sub.3 -C.sub.7 secondary alkyl or C.sub.4 -C.sub.7 tertiary alkyl, or(b) selected from the group consisting of naphthyl, anthryl, and phenanthryl optionally substituted 1 to 5 times with C.sub.3 -C.sub.7 secondary alkyl or C.sub.4 -C.sub.7 tertiary alkyl groups,R.sub.10 is C.sub.6 -C.sub.10 alkyl, aryl or alkyl aryl,and Y is H, F or Cl,are disclosed. These processes can be used to make optically enhanced and optically pure forms of the compounds, which are useful in the making of camptothecin and analogs thereof.Type: GrantFiled: April 1, 1993Date of Patent: May 24, 1994Assignee: North Carolina State UniversityInventors: Daniel L. Comins, Matthew F. Baevsky
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Patent number: 5314887Abstract: There are provided novel 1,4-dihydropyridine compounds possessing both calcium agonist and alpha.sub.1 -antagonist activity useful for treating congestive heart failure, pharmaceutical compositions containing them and methods of using these compounds to treat congestive heart failure in a mammal.Type: GrantFiled: October 30, 1992Date of Patent: May 24, 1994Assignee: The Du Pont Merck Pharmaceutical CompanyInventors: Paul E. Aldrich, Richard A. Earl, Philip Ma
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Patent number: 5290787Abstract: Non-peptidyl compounds characterized generally as azachromonyl/azachromonylalkyl-N-terminal cycloalkoxy-C-terminal amino hydroxy .beta.-amino acid derivatives are useful as renin inhibitors for treatment of hypertension. Compounds of particular interest are of the formula ##STR1## wherein R.sub.1 is selected from ##STR2## wherein each of Y and Z is independently selected from hydrido, chloro, fluoro, methoxy and dimethylamino; wherein n is a number selected from zero through four, inclusive; wherein each of R.sub.2 and R.sub.4 is independently selected from hydrido and methyl; wherein R.sub.3 is methyl or ethyl; wherein R.sub.5 is cyclohexylmethyl; wherein R.sub.6 and R.sub.Type: GrantFiled: July 16, 1992Date of Patent: March 1, 1994Assignee: G. D. Searle & Co.Inventor: Gunnar J. Hanson
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Patent number: 5273981Abstract: Novel compounds represented by the formula: ##STR1## wherein R represents hydrogen, alkyl radicals having from 1 to about 10 carbon atoms, alkenyl radicals having from 1 to about 10 carbon atoms, aryl, alkaryl and aralkyl radicals having from about 6 to about 16 carbon atoms and acyl and acyloxy radicals having from about 1 to about 10 carbon atoms, manifest glycosidase inhibition activity.Type: GrantFiled: April 16, 1992Date of Patent: December 28, 1993Assignee: Monsanto CompanyInventors: Daniel P. Getman, Gary A. DeCrescenzo
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Patent number: 5270468Abstract: Novel derivatives of 1-deoxynojirimycin are disclosed which have amino or azido substituents at C-2 and/or C-3. These compounds are useful inhibitors of lentiviruses. Methods of chemical synthesis of these derivatives and intermediates therefor are also disclosed.Type: GrantFiled: January 8, 1993Date of Patent: December 14, 1993Assignee: G. D. Searle & Co.Inventors: Ish K. Khanna, Richard A. Mueller, Richard M. Weier, Michael A. Stealey
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Patent number: 5258516Abstract: Processes for making compounds of Formulae XIV, XV, and XVII ##STR1## wherein R.sub.6 is lower alkyl, R.sub.7 is lower alkyl, R is lower alkyl, Y is H, F or Cl, R.sub.8 is a compound of Formula XVIII ##STR2## wherein n is 1, 2, or 3, R.sub.11 is C.sub.1 -C.sub.4 alkyl and R.sub.12 is the same as R.sub.11, or R.sub.11 and R.sub.12 together form cyclopentane or cyclohexane, and R.sub.13 is:(a) phenyl substituted 1 to 5 times with C.sub.3 -C.sub.7 secondary alkyl or C.sub.4 -C.sub.7 ; tertiary alkyl, or(b) selected from the group consisting of naphthyl, anthryl, and phenanthryl optionally substituted 1 to 5 times with C.sub.3 -C.sub.7 secondary alkyl or C.sub.4 -C.sub.7 tertiary alkyl groups,R.sub.10 is C.sub.6 -C.sub.10 alkyl, aryl or alkyl aryl,and Y is H, F or Cl,are disclosed. These processes can be used to make optically enhanced and optically pure forms of the compounds, which are useful in the making of camptothecin and analogs thereof.Type: GrantFiled: February 12, 1993Date of Patent: November 2, 1993Assignee: NC State UniversityInventors: Daniel L. Comins, Matthew F. Baevsky
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Patent number: 5258518Abstract: 2-Substituted tertiary carbinol derivatives of deoxynojirimycin are disclosed having the formula ##STR1## wherein R.sub.4 =an alkyl, vinyl, alkenyl, alkynyl, aryl, aralkyl, alkenylalkyl, alkylnylalkyl or CH.sub.2 Y substituent having from about 1 to 10 carbon atoms;Y=OR', SR', NR'R', or N.sub.3 ;R=H or CH.sub.3 ; andR=H or an alkyl, aralkyl, alkenylalkyl, alkynylalkyl, aralkenyl, aralkynyl or hydroxyalkyl substituent, having from about 1 to 18 carbon atoms, provided that no carbon unsaturated bond is directly attached to nitrogen.These compounds have useful antiviral activity as demonstrated against lentivirus.Type: GrantFiled: April 1, 1992Date of Patent: November 2, 1993Assignee: G. D. Searle & Co.Inventors: Ish K. Khanna, Richard A. Mueller, Richard M. Weier
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Patent number: 5254557Abstract: A compound of formula (IA) in the form of a pharmaceutically acceptable microfine powder is disclosed.Type: GrantFiled: June 1, 1992Date of Patent: October 19, 1993Assignee: Beecham Group p.l.c.Inventors: Derek R. Buckle, David G. Smith, Frederick Cassidy
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Patent number: 5252538Abstract: There are provided novel (2-imidazolin-2-yl) fused heteropyridine compounds, and intermediate compounds for the preparation thereof, and a method for controlling a wide variety of annual and perennial plant species therewith.Type: GrantFiled: January 16, 1990Date of Patent: October 12, 1993Assignee: American Cyanamid CompanyInventors: Barrington Cross, Marinus Los, Robert F. Doehner, Jr., David W. Ladner, Jerry L. Johnson, Michael E. Jung, Victor M. Kamhi, Shin-Shyong Tseng, John M. Finn, Peter J. Wepplo
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Patent number: 5250540Abstract: Aminomethyl-substituted 2,3-dihydropyrano[2,3-b]pyridines can be prepared by alkylation of corresponding amines. The novel aminomethyl-substituted dihydropyrano[2,3-b]pyridines can be used as active ingredients in medicaments, in particular for the treatment of disorders of the central nervous system.Type: GrantFiled: June 11, 1992Date of Patent: October 5, 1993Assignee: Bayer AktiengesellschaftInventors: Dieter Arlt, Hans-Georg Heine, Rudolf Schohe-Loop, Thomas Glaser, Jean M. V. De Vry
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Patent number: 5247089Abstract: Compounds of Formula I ##STR1## are made in accordance with the following scheme: ##STR2## wherein R may be loweralkyl; R.sub.t may be H, loweralkyl, loweralkoxy, or halo: R.sub.2, R.sub.3, R.sub.4, and R.sub.5 may each independently be H, amino, hydroxy, loweralkyl, loweralkoxy, loweralkylthio, di(loweralkyl)amino, cyano, methylenedioxy, formyl, nitro, halo, trifluoromethyl, aminomethyl, azido, amido, hydrazino, or any of the twenty standard amino acids bonded to the A ring via the amino-nitrogen atom; Y is H and W and X are halogen. Also disclosed are novel processes for making starting materials for the scheme given above, and novel intermediates employed in these processes.Type: GrantFiled: August 10, 1992Date of Patent: September 21, 1993Assignee: North Carolina State UniversityInventors: Daniel L. Comins, Matthew F. Baevsky
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Patent number: 5243050Abstract: Compounds of Formula I ##STR1## are made in accordance with the following scheme: ##STR2## wherein R may be loweralkyl; R.sub.1 may be H, loweralkyl, loweralkoxy, or halo; R.sub.2, R.sub.3, R.sub.4, and R.sub.5 may each independently be H, amino, hydroxy, loweralkyl, loweralkoxy, loweralkylthio, di(loweralkyl)amino, cyano, methylenedioxy, formyl, nitro, halo, trifluoromethyl, aminomethyl, azido, amido, hydrazino, or any of the twenty standard amino acids bonded to the A ring via the amino-nitrogen atom; Y is H and W and X are halogen. Also disclosed are novel processes for making starting materials for the scheme given above, and novel intermediates employed in these processes.Type: GrantFiled: October 29, 1992Date of Patent: September 7, 1993Assignee: North Carolina State UniversityInventors: Daniel L. Comins, Matthew F. Baevsky
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Patent number: 5225564Abstract: 5-Heterocyclic 2-(2-imidazolin-2-yl)pyridine compounds which are effective for the control of undesirable plant species are described. Also described are a method for the herbicidal use of said compounds and a method for their preparation.Type: GrantFiled: May 2, 1991Date of Patent: July 6, 1993Assignee: American Cyanamid CompanyInventor: John M. Finn
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Patent number: 5221744Abstract: Arylaminocarbonyl compounds of the formula (I) ##STR1## wherein R.sub.2-6, X.sub.1, A and m are as defined in the disclosure, intermediates therefore, synthesis thereof, and the use of said compounds for the control of weeds are described.Type: GrantFiled: August 17, 1992Date of Patent: June 22, 1993Assignee: Sandoz Ltd.Inventors: Karl Seckinger, Karlheinz Milzner, Fred Kuhnen, Sasank S. Mohanty
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Patent number: 5218121Abstract: Novel compounds represented by the formula: ##STR1## wherein R represents hydrogen, optionally substituted alkyl radicals having from 1 to about 10 carbon atoms, optionally substituted alkenyl radicals having from 1 to about 10 carbon atoms, optionally substituted aryl, alkaryl and aralkyl radicals having from about 6 to about 16 carbon atoms and optionally substituted acyl and acyloxy radicals having from about 1 to about 10 carbon atoms, manifest glycosidase inhibition activity.Type: GrantFiled: March 2, 1992Date of Patent: June 8, 1993Assignee: Monsanto CompanyInventors: Daniel P. Getman, Gary A. DeCrescenzo
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Patent number: 5214051Abstract: Thiazolyl and oxazolyl [5,4-c] piperidyl-substituted quinolone-carboxylic acids and related analogs thereof having antibacterial properties are disclosed.Type: GrantFiled: May 16, 1991Date of Patent: May 25, 1993Assignee: Pfizer Inc.Inventors: Katherine E. Brighty, John A. Lowe, III, Paul R. McGuirk
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Patent number: 5212317Abstract: Processes for making compounds of Formulae XIV, XV, and XVII ##STR1## wherein R.sub.6 is lower alkyl, R.sub.7 is lower alkyl, R is lower alkyl, Y is H, F or Cl, R.sub.8 is a moiety of Formula XVIII ##STR2## wherein n is 1, 2, or 3, R.sub.11 is C.sub.1 -C.sub.4 alkyl and R.sub.12 is the same as R.sub.11, or R.sub.11 and R.sub.12 together form cyclopentane or cyclohexane, and R.sub.13 is:(a) phenyl substituted 1 to 5 times with C.sub.3 -C.sub.7 secondary alkyl or C.sub.4 -C.sub.7 tertiary alkyl, or(b) selected from the group consisting of naphthyl, anthryl, and phenanthryl optionally substituted 1 to 5 times with C.sub.3 -C.sub.7 secondary alkyl or C.sub.4 -C.sub.7 tertiary alkyl groups,R.sub.10 is C.sub.6 -C.sub.10 alkyl, aryl or alkyl aryl,and Y is H, F or Cl,are disclosed. These processes can be used to make optically enhanced and optically pure forms of the compounds, which are useful in the making of camptothecin and analogs thereof.Type: GrantFiled: June 18, 1992Date of Patent: May 18, 1993Assignee: North Carolina State UniversityInventors: Daniel L. Comins, Matthew F. Baevsky
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Patent number: 5208342Abstract: In one embodiment this invention provides a process for converting a pyridine-2,3-dicarboxylic acid diester to the corresponding cyclic anhydride directly, without any recovery and purification of the pyridine-2,3-dicarboxylic acid intermediate.An important aspect of the invention process is the utility of pure pyridine-2,3-dicarboxylic acid diester starting matter. A procedure for providing pure diester starting material is demonstrated.Type: GrantFiled: March 30, 1992Date of Patent: May 4, 1993Assignee: Hoechst Celanese CorporationInventors: B. Franklin Gupton, John Saukaitis
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Patent number: 5200420Abstract: 2,6-dialkyl-4-(benzothiazol- or benzoxazol-7-yl)-1,4-dihydropyridines which exhibit positive inotropic action with largely neutral vascular behavior, of the formula ##STR1## in which R.sup.1 and R.sup.5 are identical or different and represent straight-chain or branched alkyl having up to 8 carbon atoms,R.sup.2 represents nitro or cyano, orR.sup.1 and R.sup.2 together form a lactone ring of the formula ##STR2## R.sup.3 represents a radical of the formula ##STR3## R.sup.4 -R.sup.7 are defined hereinafter and physiologically acceptable salts thereof.Type: GrantFiled: March 29, 1991Date of Patent: April 6, 1993Assignee: Bayer AktiengesellschaftInventors: Siegfried Goldmann, Horst Boshagen, Jurgen Stoltefuss, Alexander Straub, Rainer Gross, Joachim Hutter, Siegbert Hebisch, Martin Bechem
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Patent number: 5198434Abstract: The invention concerns pharmaceutically useful compounds of the formula I, in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, n, m, X, Y and Z have the various meanings defined herein, and their non-toxic salts, and pharmaceutical compositions containing them. The novel compounds are of value in treating conditions such as hypertension and congestive heart failure. The invention further concerns processes for the manufacture of the novel compounds and the use of the compounds in medical treatment.Type: GrantFiled: February 11, 1992Date of Patent: March 30, 1993Assignee: Imperial Chemical Industries PLCInventors: Robert H. Bradbury, David A. Roberts
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Patent number: 5190938Abstract: The invention relates to compounds of formula ##STR1## in which R.sub.1 is selected from the groups R.sub.3 and OR.sub.3, R is selected from H and a group CHR.sub.2 R', in which R.sub.2 is selected from H, alkyl, carboxy and carboxamido and R', is H, alkyl or phenyl, Z represents S or O; and m and n, which may be identical or different, equal 1 or 2, and their N-oxides, salts and quaternary ammonium derivatives.The invention also relates to the process for preparing these compounds, as well as to pharmaceutical compositions containing them.Type: GrantFiled: October 2, 1990Date of Patent: March 2, 1993Assignee: SanofiInventors: Alain Badorc, Marie-Francoise Bordes, Daniel Frehel, Jean-Marc Herbert
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Patent number: 5191082Abstract: Compounds of Formula I ##STR1## are made in accordance with the following scheme: ##STR2## wherein R may be loweralkyl; R.sub.1 may be H, loweralkyl, loweralkoxy, or halo; R.sub.2, R.sub.3, R.sub.4, and R.sub.5 may each independently be H, amino, hydroxy, loweralkyl, loweralkoxy, loweralkylthio, di(loweralkyl)amino, cyano, methylenedioxy, formyl, nitro, halo, trifluoromethyl, aminomethyl, azido, amido, hydrazino, or any of the twenty standard amino acids bonded to the A ring via the amino-nitrogen atom; Y is H and W and X are halogen. Also disclosed are novel processes for making starting materials for the scheme given above, and novel intermediates employed in these processes.Type: GrantFiled: August 10, 1992Date of Patent: March 2, 1993Assignee: North Carolina State UniversityInventors: Daniel L. Comins, Matthew F. Baevsky
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Patent number: 5189047Abstract: The present invention is directed to compounds of formula (I) and pharmaceutically acceptable salts thereof: ##STR1## wherein Y, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 , a and b are as defined in the Specification, having pharmacological activity, to a process for their preparation, and to their use as pharmaceuticals.Type: GrantFiled: July 20, 1990Date of Patent: February 23, 1993Assignee: Beecham Group p.l.c.Inventors: Michael S. Hadley, Graham E. Jones
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Patent number: 5185345Abstract: The present invention deals with 4-amidino chroman and 4-amidino pyrano (3,2-c) pyridine derivatives, a process for their preparation and pharmaceutical compositions containing them. Said derivatives have antihypertensive and antiarythmic activities. They respond to formula ##STR1## in which: A+B.dbd.--CH.dbd.CH--CH.dbd.N-- ou --CH.dbd.CR.sub.4 --CR.sub.5 .dbd.CH--; X.dbd.N,N.fwdarw.O, C--Z;R.sub.1 .dbd.H, CN, NO.sub.2, C.sub.1 -C.sub.4, alkyl, OH, C.sub.1 -C.sub.4 alkoxy, CF.sub.3 CO--, CH.sub.3 --SO.sub.2 --, .rho.--SO.sub.2 --;R.sub.2 .dbd.H;R.sub.3 .dbd.OH ou OCOCH.sub.3 ou R.sub.2 +R.sub.3 .dbd.double bond.Type: GrantFiled: March 12, 1992Date of Patent: February 9, 1993Assignee: SanofiInventors: Georges Garcia, Patrick Gautier, Dino Nisato, Richard Roux
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Patent number: 5180417Abstract: Disclosed herein are derivatives of 4-((aryloxy)phenoxy)fluoroalkanoic acid and their use as active herbicides for the pre- and postemergent control of grassy weeds, especially in the presence of broadleaf crops.Type: GrantFiled: April 12, 1991Date of Patent: January 19, 1993Assignee: DowElancoInventor: James A. Turner
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Patent number: 5179093Abstract: Compounds of the formula ##STR1## or a pharmaceutically acceptable salt thereof wherein, R is H, halogen, (C.sub.1 -C.sub.6) alkyl, N(C.sub.1 -C.sub.6 alkyl/aryl).sub.2, OH, O--(C.sub.1 -C.sub.6) alkyl/aryl, CH.sub.2 OH, COOH, COO-alkyl/aryl, SO.sub.2 NH.sub.2, or SO.sub.2 NH (C.sub.1 -C.sub.6 alkyl/aryl);R.sub.1 is C.sub.1 -C.sub.6 alkyl, cycloalkyl, C.sub.2 -C.sub.6 alkenyl, heteroaryl, substituted heteroaryl, heterocycloalkyl, --CH.sub.2 -aryl, --CH.sub.2 -substituted aryl, --CH.sub.2 -heteroaryl, or --CH.sub.2 -substituted heteroaryl;R.sub.2 is H, C.sub.1 -C.sub.6 alkyl or aryl; ##STR2## is an aromatic ring or a heteroaromatic ring; and X is O or N-(alkyl/aryl/alkyl-aryl/alkoxylalkoxyaryl)are described. These compounds are useful as agents for treating viruses.Type: GrantFiled: May 10, 1991Date of Patent: January 12, 1993Assignee: Schering CorporationInventors: Adriano Afonso, Stuart W. McCombie, Jay Weinstein
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Patent number: 5175168Abstract: Novel compounds represented by the formula: ##STR1## wherein R represents hydrogen, optionally substituted alkyl radicals having from 1 to about 10 carbon atoms, optionally substituted alkenyl radicals having from 1 to about 10 carbon atoms, optionally substituted aryl, alkaryl and aralkyl radicals having from about 6 to about 16 carbon atoms and optionally substituted acyl and acyloxy radicals having from about 1 to about 10 carbon atoms, manifest glycosidase inhibition activity.Type: GrantFiled: March 22, 1991Date of Patent: December 29, 1992Assignee: Monsanto CompanyInventors: Daniel P. Getman, Gary A. DeCrescenzo
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Patent number: 5166148Abstract: There are provided novel 1,4-dihydropyridine compounds possessing both calcium agonist and alpha.sub.1 -antagonist activity useful for treating congestive heart failure, pharmaceutical compositions containing them and methods of using these compounds to treat congestive heart failure in a mammal.Type: GrantFiled: July 9, 1990Date of Patent: November 24, 1992Assignee: The Du Pont Merck Pharmaceutical CompanyInventors: Paul E. Aldrich, Richard A. Earl, Philip Ma
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Patent number: 5166147Abstract: There are provided novel 1,4-dihydropyridine compounds, compositions containing them and methods of using them to treat congestive heart failure.Type: GrantFiled: July 9, 1990Date of Patent: November 24, 1992Assignee: The Du Pont Merck Pharmaceutical CompanyInventor: Richard A. Earl
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Patent number: 5162550Abstract: Bisphthalide lactones of formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each independently of one another hydrogen, alkyl of at most 12 carbon atoms which is unsubstituted or substituted by halogen, hydroxy, cyano, tetrahydrofuryl or lower alkoxy; or are acyl of 1 to 12 carbon atoms, cycloalkyl of 5 to 10 carbon atoms or unsubstituted aralkyl or aryl, or aralkyl or aryl each substituted by halogen, cyano, nitro, trifluormethyl, lower alkyl, lower alkoxy, lower alkoxycarbonyl, --NX'X"-- or 4--NX'X--"phenylamino, wherein X' and X" are each independently of the other hydrogen, lower alkyl, cyclohexyl, benzyl or phenyl, or the pairs of substituents --NR.sub.1 R.sub.2 and --NR.sub.3 R.sub.4 are each a 5- or 6-membered, preferably saturated, heterocyclic radical, V.sub.1 and V.sub.2 are hydrogen, halogen, lower alkyl, C.sub.1 -C.sub.12 alkoxy, C.sub.1 -C.sub.Type: GrantFiled: August 24, 1990Date of Patent: November 10, 1992Assignee: Ciba-Geigy CorporationInventors: Rudolf Zink, Ian J. Fletcher
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Patent number: 5162338Abstract: 4 Aminoaryldihydropyridines of the formula ##STR1## in which R.sup.1 is hydrogen or an organic radical, preferably methyl or ethyl,R.sup.2 is hydrogen, C.sub.1 -C.sub.5 - alkyl, --CN, --NH.sub.2, --CH.sub.2 or --CH.sub.2 OH, preferably methyl,R.sup.3 is hydrogen or alkyl, preferably hydrogen,Y is --CO-- or --SO.sub.2 --, andR.sup.4 is an organic radical, orY-R.sup.4 is hydrogen,and physiologically acceptable salts thereof, are circulation-active and effective for improving myocardial contractility, for raising blood pressure, for lowering blood sugar, for reducing mucosal swelling and for controlling the salt and fluid balance.Type: GrantFiled: October 18, 1991Date of Patent: November 10, 1992Assignee: Bayer AktiengesellschaftInventors: Siegfried Goldmann, Matthias Schramm, Rainer Gross, Gunther Thomas, Martin Bechem, Michael Kayser
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Patent number: 5162532Abstract: Compounds of Formula I ##STR1## are made in accordance with the following scheme: ##STR2## wherein R may be loweralkyl; R.sub.1 may be H, loweralkyl, loweralkoxy, or halo; R.sub.2, R.sub.3, R.sub.4, and R.sub.5 may each independently be H, amino, hydroxy, loweralkyl, loweralkoxy, loweralkylthio, di(loweralkyl)amino, cyano, methylenedioxy, formyl, nitro, halo, trifluoromethyl, aminomethyl, azido, amido, hydrazino, or any of the twenty standard amino acids bonded to the A ring via the amino-nitrogen atom; Y is H and W and X are halogen. Also disclosed are novel processes for making starting materials for the scheme given above, and novel intermediates employed in these processes.Type: GrantFiled: December 20, 1990Date of Patent: November 10, 1992Assignee: North Carolina State UniversityInventors: Daniel L. Comins, Matthew F. Baevsky
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Patent number: 5155116Abstract: Compounds of general formula (I): ##STR1## in which: R.sub.1 and R.sub.2 each represent a hydrogen atom or, with the nitrogen and oxygen which bear them, form an --O--CO--N link,W represents a halogen atom or a lower alkyl or alkoxy group optionally substituted with one or more halogen atoms, such as trifluoromethyl, and m being between 0 and 3,A is a linear or branched alkyl radical comprising from 1 to 6 carbon atoms,R.sub.3 and R.sub.4 are defined in the description have medicinal properties.Type: GrantFiled: June 6, 1991Date of Patent: October 13, 1992Assignee: Adir et CompagnieInventors: Gerald Guillaumet, Christine Flouzat, Daniel H. Caignard, Pierre Renard, Michelle Devissaguet, Beatrice Guardiola
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Patent number: 5144037Abstract: Antiviral O-acylated derivatives of 1,5-dideoxy-1,5-imino-D-glucitol are disclosed that contain an N-alkyl or N-aroyl radical in which from one to four of the free hydroxyl groups are O-acylated with carboxylic alkanoyl radicals selected from the group consisting of .omega.,.omega.,.omega.-trifluoro alkanoyl having from three to eight carbon atoms, carboxylic cycloalkanoyl groups having from four to eight carbon atoms and carboxylic acyclic alkanoyl groups having from two to ten carbon atoms, wherein the N-aroyl radical is selected from the group consisting of p-decylbenzoyl, 3-(p-chlorophenoxy)propanoyl, 2-(acetyloxy)benzoyl, [1,1'-biphenyl]-4-ylcarbonyl, 2-thiopheneacetyl, trans-3-furanacryloyl, 3-methoxyphenylacetyl and 3-(trifluoromethyl)benzoyl, and wherein the N-alkyl contains from one to fourteen carbon atoms, provided that when N-alkyl contains from one to five carbon atoms the O-acylated groups are .omega.,.omega.,.omega.-trifluoro alkanoyl or carboxylic cycloalkanoyl.Type: GrantFiled: January 10, 1991Date of Patent: September 1, 1992Assignee: G. D. Searle & Co.Inventors: Richard A. Partis, Francis J. Koszyk, Richard A. Mueller
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Patent number: 5140031Abstract: Novel compounds having the formula ##STR1## wherein ##STR2## are disclosed. These compounds have potassium channel activating activity and are useful, for example, as cardiovascular agents, especially as antiischemic agents.Type: GrantFiled: February 27, 1991Date of Patent: August 18, 1992Assignee: E. R. Squibb & Sons, Inc.Inventors: Karnail Atwal, Gary J. Grover, Kyoung S. Kim
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Patent number: 5137881Abstract: Substituted pyrido-oxazines can be prepared by reduction of the corresponding ketones. They are useful active compounds in medicaments, in particular for the treatment of hyperlipoproteinaemia, lipoproteinaemia and arteriosclerosis.Type: GrantFiled: July 16, 1991Date of Patent: August 11, 1992Assignee: Bayer AktiengesellschaftInventors: Walter Hubsch, Rolf Angerbauer, Peter Fey, Hilmar Bischoff, Joachim Bender, Delf Schmidt
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Patent number: 5132310Abstract: Racemic Compounds of the formula ##STR1## A is --C.tbd.C--R.sub.6, --CH.sub.2 --CH.sub.2 --R.sub.7 or ##STR2## R.sub.1 is hydrogen or lower alkanoyl, R.sub.2, R.sub.3, and R.sub.4 independently are hydrogen or lower alkyl,R.sub.5 is lower alkyl,R.sub.6 is a heteroaromatic radical or an aromatic radical selected from phenyl, naphthyl or phenanthryl, which aromatic radical may optionally be substituted by one or more substituents selected from chlorine, fluorine, lower alkyl, lower alkoxy, phenyl lower alkoxy, lower alkanoyl, lower alkanoyloxy, hydroxy-lower alkyl, carboxy, lower alkoxycarbonyl, hydroxyimino lower alkyl, amino, amino lower alkyl, mono- or di-lower alkylamino, mono- or di-lower alkylamino-lower alkyl, lower alkanoylamino, aminocarbonyl, lower alkylaminocarbonyl, lower dialkylaminocarbonyl, trifluoroacetylamino, trifluoromethyl, hydroxy, pyridyl, or on adjacent carbons can be ##STR3## wherein R' is hydrogen, lower alkanoyl, trifluoroacetyl and R" hydrogen or lower alkyl,R.sub.Type: GrantFiled: December 14, 1990Date of Patent: July 21, 1992Assignee: Hoffmann-La Roche Inc.Inventor: Armin Walser
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Patent number: 5130320Abstract: Novel compounds represented by the formula: ##STR1## wherein R represents hydrogen, optionally substituted alkyl radicals having from 1 to about 10 carbon atoms, optionally substituted alkenyl radicals having from 1 to about 10 carbon atoms, optionally substituted aryl, alkaryl and aralkyl radicals having from about 6 to about 16 carbon atoms and optionally substituted acyl and acyloxy radicals having from about 1 to about 10 carbon atoms, manifest glycosidase inhibition activity.Type: GrantFiled: March 21, 1991Date of Patent: July 14, 1992Assignee: Monsanto CompanyInventors: Daniel P. Getman, Gary A. DeCrescenzo
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Patent number: 5130311Abstract: The invention relates to the analgesic compounds of general formula (I): ##STR1## in which: R.sub.1, R.sub.2, R.sub.3, R.sub.4, A, Z and m are as defined in the description, their isomers, epimers and diastereoisomers, their addition salts with a pharmaceutically acceptable acid and, when R.sub.1 and R.sub.2 each represent a hydrogen atom, their addition salts with a pharmaceutically acceptable base.Type: GrantFiled: November 15, 1991Date of Patent: July 14, 1992Assignee: Adir et CompagnieInventors: Gerald Guillaumet, Christine Flouzat, Michelle Devissaguet, Pierre Renard, Daniel H. Caignard, Gerard Adam
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Patent number: 5116849Abstract: The present invention deals with 4-amidino chroman and 4-amidino pyrano (3,2-c) pyridine derivatives, a process for their preparation and pharmaceutical compositions containing them. Said derivatives have antihypertensive and antiarrhythmic activities. They respond to formula ##STR1## in which: A+B=--CH.dbd.CH--CH.dbd.N--or--CH.dbd.CR.sub.4 --CR.sub.5 .dbd.CH--;X=N, N.fwdarw.O, C--Z;R.sub.1 =H, CN, NO.sub.2, C.sub.1 -C.sub.4 alkyl, OH, C.sub.1 -C.sub.4 alkoxy, CF.sub.3 CO--, CH.sub.3 --SO.sub.2 --, .phi.--SO.sub.2 --;R.sub.2 =H;R.sub.3 =OH or OCOCH.sub.3 or R.sub.2 +R.sub.3 =double bond.Type: GrantFiled: October 31, 1990Date of Patent: May 26, 1992Assignee: SanofiInventors: Georges Garcia, Patrick Gautier, Dino Nisato, Richard Roux
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Patent number: 5116970Abstract: A series of psychotropic heterobicycloalkylpiperazine derivatives having the structure ##STR1## wherein V is a 3- or 4-membered unsaturated chain, containing all carbon atoms when 4-membered, or when a 3-membered chain, V contains an oxygen or sulfur atom as one of the members; R is H or C.sub.1-4 alkyl; W is CH, N, CH.sub.2, or a chemical bond; X is CH, N, SO.sub.2, or CO, with the proviso that both W and X cannot simultaneously be N; and Z is a heteroaromatic ring system. These compounds are useful antipsychotic and/or anxiolytic agents.Type: GrantFiled: December 20, 1990Date of Patent: May 26, 1992Inventors: James S. New, William J. Christopher
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Patent number: 5109008Abstract: Compounds are disclosed of formula (I) ##STR1## wherein R.sub.1 represents hydrogen, unsubstituted or substituted C.sub.1-6 alkyl, halogen, --COR.sub.4 or --CO.sub.2 R.sub.4 (where R.sub.4 represents hydrogen or unsubstituted or substituted C.sub.1-6 alkyl);R.sub.2 and R.sub.3 are the same or different and are C.sub.1-6 alkyl or C.sub.3-6 alkenyl; or --NR.sub.2 R.sub.3 forms a 5-membered (optionally containing an oxygen atom adjacent to the nitrogen) or a 6-membered ring, which ring optionally contains one unit of unsaturation and which is unsubstituted or substituted by hydroxy, C.sub.1-6 acyloxy, oxo, optionally substituted methylidene, --COR.sub.5 (where R.sub.5 represents C.sub.1-6 alkyl, OR.sub.6 or --NHR.sub.6, andR.sub.6 represents hydrogen, C.sub.1-6 alkyl, aryl or ar(C.sub.1-6)alkyl) or said ring is substituted by .dbd.NOR.sub.7 (where R.sub.7 represents C.sub.1-6 alkyl);Z represents --O-- or --S--;X represents a direct bond, --CH.sub.2 -- or --CH.sub.Type: GrantFiled: October 18, 1989Date of Patent: April 28, 1992Assignee: Glaxo Group LimitedInventors: David I. C. Scopes, Duncan B. Judd, David J. Belton
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Patent number: 5097044Abstract: Pyran-containing phthalides of the formula ##STR1## in which R is hydrogen, alkyl which has not more than 12 carbon atoms and is unsubstituted or substituted by halogen, cyano, hydroxyl or lower alkoxy, or is cycloalkyl, phenalkyl or phenyl each of which is unsubstituted or substituted, or an unsubstituted or substituted heterocyclic radical, R' is hydrogen, or R together with R' is C.sub.2 -C.sub.3 alkylene which is unsubstituted or substituted by methyl,X is hydrogen, alkyl having 1 to 12 carbon atoms or a monocyclic or polycyclic aromatic or heteroaromatic radical and the ring A is a benzene or naphthalene ring which is unsubstituted or monosubstituted or polysubstituted by halogen, lower alkyl, lower alkoxy or lower alkoxycarbonyl, and the ring B is an aromatic or heteroaromatic radical which has 6 ring atoms and which can contain an aromatic fused ring, it being possible for both the ring B and the fused ring to be substituted.Type: GrantFiled: September 20, 1990Date of Patent: March 17, 1992Assignee: Ciba-Geigy CorporationInventor: Rox Phaff
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Patent number: 5077408Abstract: Process for the synthesis of compounds of formula (I): ##STR1## their pyridinium salts and N-oxides, in which formula: the nitrogen of the pyridine ring is situated in the .alpha.-, .beta.-, .gamma.- or .delta.-position with respect to the ring junction;R.sup.1 represents a halogen, a substituted or unsubstituted alkyl, a substituted or unsubstituted alkoxy or a nitro, substituted or unsubstituted amino, phenyl or cyano group;0.ltoreq.m.ltoreq.2;R.sup.2 represents a lower alkyl or cycloalkyl group, a 5- or 6-membered heterocycle containing 1 or 2 hetero atoms, substituted or otherwise, or an aryl group ##STR2## such that: R.sup.3 represents a halogen, a substituted or unsubstituted alkyl, a substituted or unsubstituted alkoxy or a nitro, phenyl, substituted or unsubstituted sulfonyl, cyano, thioalkyl, substituted or unsubstituted amino, substituted or unsubstituted sulfinyl, mercapto, hydroxyl or ester group,0.ltoreq.n.ltoreq.Type: GrantFiled: September 17, 1990Date of Patent: December 31, 1991Assignee: Science et OrganisationInventors: Gerald Guillaumet, Christine Flouzat