Five-membered Ring In Substituent Q Patents (Class 564/189)
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Patent number: 5777138Abstract: A process for amidating a 2-azabicyclo?2.2.1!heptan-3-one or a 2-azabicyclo?2.2.1!hept-5-en-3-one by reaction with an amine, to form the corresponding ring-opened amide, is modified by the addition of an additive that accelerates the rate of reaction to an extent that the reaction can be carried out at atmospheric pressure.Type: GrantFiled: March 12, 1997Date of Patent: July 7, 1998Assignee: Chriroscience LimitedInventors: Robin Mark Bannister, Neil Henderson, Graham Ruecroft
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Patent number: 5773654Abstract: Compounds of the formula ##STR1## where the dotted line represents a bond or the absence of a bond, the wavy lines represent bonds which are either in cis or trans configuration; R.sub.1 represents H, or CO-R.sub.2 where R.sub.2 is lower alkyl of 1 to 6 carbons, carbocyclic aryl or heterocyclic aryl; or carbocyclic aryl or heteroaryl substituted lower alkyl group; X represents CO-NR.sub.3 R.sub.4, CH.sub.2 OH, CH.sub.2 OR.sub.5, CH.sub.2 O-COR.sub.6, and CH.sub.2 -NR.sub.3 R.sub.4, where R.sub.3 and R.sub.4 independently are H or lower alkyl, R.sub.5 is lower alkyl of 1 to 6 carbons, and R.sub.6 is lower alkyl of 1 to 6 carbons, carbocyclic aryl or heterocyclic aryl; or carbocyclic aryl or heteroaryl substituted lower alkyl group, and n is an integer between 0 and 8 are capable of lowering intraocular pressure in the eye of a mammal.Type: GrantFiled: July 24, 1997Date of Patent: June 30, 1998Assignee: AllerganInventors: Michael E. Garst, Robert M. Burk
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Patent number: 5753709Abstract: Certain N-acyl 2-aryl cyclopropylmethylamine derivatives are useful as melatonergic agents.Type: GrantFiled: May 9, 1996Date of Patent: May 19, 1998Assignee: Bristol-Myers Squibb CompanyInventors: Daniel J. Keavy, Michael F. Parker, Ronald J. Mattson, Graham Johnson
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Patent number: 5750733Abstract: The present invention relates to novel hydroxy-containing alkyl glycamide surfactants and detergent composition comprising said surfactants. Since they surprisingly provide low foam, these surfactants can be used as cleansing surfactants in applications where low foaming is desirable.Type: GrantFiled: August 6, 1996Date of Patent: May 12, 1998Assignee: Lever Brothers Company, Division of Conopco, Inc.Inventors: Robert Vermeer, Bijan Harichian
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Patent number: 5736578Abstract: Novel substituted fluorene compunds of Formula I are active as melatonergic agents: ##STR1## wherein: X=H, halogen, OH or OZ;Z=C.sub.1-6 alkyl; --(CH.sub.2).sub.m --CF.sub.3 (m=0-2); CD.sub.3 ; or ##STR2## n=1 or 2; and R=C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl, C.sub.2-4 alkenyl, halogen substituted C.sub.1-6 alkyl, or C.sub.1-6 alkoxy substituted C.sub.1-6 alkyl.Type: GrantFiled: May 10, 1996Date of Patent: April 7, 1998Assignee: Bristol-Myers Squibb CompanyInventors: Brett T. Watson, Katherine S. Takaki, Joseph P. Yevich, James R. Epperson, George N. Karageorge, Karen L. Leboulluec
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Patent number: 5728875Abstract: .alpha.-Amino acid amides of the formula I ##STR1## in which n is the number zero or one;R.sub.1 is C.sub.1 -C.sub.12 alkyl, which is unsubstituted or can be substituted by C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.3 -C.sub.8 cycloalkyl, cyano, C.sub.1 -C.sub.6 alkoxycarbonyl, C.sub.3 -C.sub.6 alkenyloxycarbonyl or C.sub.3 -C.sub.6 alkynyloxycarbonyl; C.sub.3 -C.sub.8 cycloalkyl; C.sub.2 -C.sub.12 alkenyl;C.sub.2 -C.sub.12 alkynyl; C.sub.1 -C.sub.12 halogenoalkyl or a group NR.sub.13 R.sub.14 ; in which R.sub.13 and R.sub.14 independently of one another are hydrogen or C.sub.1 -C.sub.6 alkyl or together are tetra- or pentamethylene;R.sub.2 and R.sub.3 independently of one another are hydrogen; C.sub.1 -C.sub.8 alkyl; C.sub.1 -C.sub.8 alkyl which is substituted by hydroxyl, C.sub.1 -C.sub.4 alkoxy, mercapto or C.sub.1 -C.sub.4 alkylthio; C.sub.3 -C.sub.8 alkenyl;C.sub.3 -C.sub.8 alkynyl; C.sub.3 -C.sub.8 cycloalkyl or C.sub.3 -C.sub.8 cycloalkyl-C.sub.1 -C.sub.Type: GrantFiled: August 26, 1996Date of Patent: March 17, 1998Assignee: Novartis CorporationInventor: Martin Zeller
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Patent number: 5710331Abstract: Preparation of N-alkenyl carboxamides of the general formula I ##STR1## in which the radicals R.sup.1 to R.sup.4 independently stand for hydrogen or for aliphatic, cycloaliphatic, or aromatic radicals, which optionally carry inert substituents, wherein an amide of the general formula II ##STR2## in which the radical R.sup.1 has the above meaning, and a carbonyl compound of the general formula III ##STR3## in which the radicals R.sup.2 to R.sup.4 have the above meanings, are caused to react in the presence of a base, said reaction being eithera) carried out in the presence of a carboxylic acid derivative of the general formula IV ##STR4## in which the radical R.sup.5 stands for hydrogen or an alkyl or aryl group and X is a halogen, alkoxy, or carboxylalkyl radical, orb) continued in the presence of a carboxylic acid derivative of the formula IV, and the amide of the formula I is isolated.Type: GrantFiled: October 26, 1995Date of Patent: January 20, 1998Assignee: BASF AktiengesellschaftInventors: Marc Heider, Thomas Ruhl, Jochem Henkelmann
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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: 5684198Abstract: Amides having formula I: ##STR1## wherein E, X, R.sup.2 and R.sup.3 have the meanings given in the specification, and pharmaceutically acceptable salts and pharmaceutically acceptable in vivo hydrolysable esters thereof,which are useful in the treatment of urinary incontinence. Further provided are processes for preparing the aides and pharmaceutical compositions containing them.Type: GrantFiled: August 23, 1996Date of Patent: November 4, 1997Assignee: Imperial Chemical Industries, PLCInventors: Keith Russell, Cyrus John Ohnmacht, Keith Hopkinson Gibson
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Patent number: 5661186Abstract: Certain tetralinyl- and indanyl-ethylamides are useful central nervous system agents.Type: GrantFiled: December 21, 1995Date of Patent: August 26, 1997Assignee: Bristol-Myers Squibb Co.Inventors: Katherine S. Takaki, Brett T. Watson, Graham S. Poindexter, James R. Epperson
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Patent number: 5654478Abstract: N-Alkenylcarboxamides of the formula I ##STR1## where at least one of the radicals R.sup.1 is hydrogen, the second radical R.sup.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl and R.sup.2 is hydrogen or an aliphatic, cycloaliphatic or aromatic radical, are prepared by reacting an alkenyl carboxylate of the formula II ##STR2## where R.sup.1 has the abovementioned meanings and R.sup.3 is hydrogen or an aliphatic, cycloaliphatic or aromatic radical, and a carboxamide of the general formula III ##STR3## where R.sup.2 has the abovementioned meanings, in the presence of a base.Type: GrantFiled: August 10, 1995Date of Patent: August 5, 1997Assignee: BASF AktiengesellschaftInventors: Thomas Ruhl, Jochem Henkelmann, Marc Heider, Bernd Fiechter
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Patent number: 5621144Abstract: New compounds are described typically having the formula CH.sub.3 C(CH.sub.2 R).sub.3 or ZCH.sub.2 C(CH.sub.2 R).sub.3 where R is a fluorohydrocarbon or perfluorocarbon group, preferably containing 4-16 carbon atoms and more F atoms that H atoms. Z is a hydrophilic group which may make the compound self-emulsifiable. The compounds are useful as oxygen transport agents in vivo, for which purpose aqueous emulsions are used, as a blood substitute.Type: GrantFiled: January 9, 1995Date of Patent: April 15, 1997Assignee: Isis Innovation LimitedInventor: Stephen R. Cooper
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Patent number: 5591775Abstract: The invention relates to a compound selected from those of formula (I): ##STR1## in which R, R.sub.1, R.sub.2 and R.sub.3 are as defined herein for use in the treatment of a disorder of the melatoninergic system.Type: GrantFiled: December 6, 1994Date of Patent: January 7, 1997Assignee: Adir et CompagnieInventors: Patrick Depreux, Hamid A. Mansour, Daniel Lesieur, Fran.cedilla.ois Lefoulon, Pierre Renard, Gerard Adam, Philippe Delagrange
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Patent number: 5585519Abstract: .alpha.-Amino acid amides of the formula I ##STR1## in which n is the number zero or one;R.sub.1 is C.sub.1 -C.sub.12 alkyl, which is unsubstituted or can be substituted by C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.3 -C.sub.8 cycloalkyl, cyano, C.sub.1 -C.sub.6 alkoxycarbonyl, C.sub.3 -C.sub.6 alkenyloxycarbonyl or C.sub.3 -C.sub.6 alkynyloxycarbonyl; C.sub.3 -C.sub.8 cycloalkyl; C.sub.2 -C.sub.12 alkenyl; C.sub.2 -C.sub.12 alkynyl; C.sub.1 -C.sub.12 halogenoalkyl or a group NR.sub.13 R.sub.14 ; in whichR.sub.13 and R.sub.14 independently of one another are hydrogen or C.sub.1 -C.sub.6 alkyl or together are tetra- or pentamethylene;R.sub.2 and R.sub.3 independently of one another are hydrogen; C.sub.1 -C.sub.8 alkyl; C.sub.1 -C.sub.8 alkyl which is substituted by hydroxyl, C.sub.1 -C.sub.4 alkoxy, mercapto or C.sub.1 -C.sub.4 alkylthio; C.sub.3 -C.sub.8 alkenyl; C.sub.3 -C.sub.8 alkynyl; C.sub.3 -C.sub.8 cycloalkyl or C.sub.3 -C.sub.8 cycloalkyl-C.sub.1 -C.sub.Type: GrantFiled: April 28, 1995Date of Patent: December 17, 1996Assignee: Ciba-Geigy CorporationInventor: Martin Zeller
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Patent number: 5547984Abstract: Certain N-acetonyl-substituted-amides of the formula: ##STR1## wherein A is a heterocycle, a phenylalkyl, a phenylalkoxy, naphthyl, cycloalkyl, alkoxyalkyl, alkyl, haloalkyl or alkenyl group; X, Y and Z are selected from the group consisting of hydrogen, halo, cyano, thiocyano, isothiocyano, methylsulfonyloxy, thio(C.sub.1 -C.sub.2)alkyl, (C.sub.1 -C.sub.2)alkoxy, carbamoyl, dithiocarbamoyl, hydroxy, azide, trifluoromethylcarboxy, (C.sub.1 -C.sub.4)alkylcarbonyloxy, phenylcarbonyloxy, phenoxy, thiophenyl, imidazolyl or triazolyl group as described herein; R.sup.1 and R.sup.2 are each independently a hydrogen atom or a (C.sub.1 -C.sub.6)alkyl group; and compositions containing these amides are fungicidally active, particularly against phytopathogenic fungi.Type: GrantFiled: June 6, 1995Date of Patent: August 20, 1996Assignee: Rohm and Haas CompanyInventor: Ashok K. Sharma
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Patent number: 5545665Abstract: The invention relates to 7-[5-hydroxy-2-(hydroxyhydrocarbyl or heteroatom-substituted hydroxy hydrocarbyl)-3-hydroxycyclopentyl(enyl)] heptanoic or heptenoic acids and derivatives of said acids, wherein one or more of said hydroxy groups are replaced by an ether group. The compounds of the present invention are potent ocular hypotensives, and are particularly suitable for the management of glaucoma.Type: GrantFiled: December 28, 1993Date of Patent: August 13, 1996Assignee: AllerganInventor: Robert M. Burk
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Patent number: 5541228Abstract: New melatonergic agents are phenyl alkanyl or phenyl alkyl substituted carboxamides and ureas of Formula I: ##STR1## wherein: R.sub.1 =C.sub.1-3 alkyl, allyl, C.sub.3-6 cycloalkyl substituted C.sub.1-4 alkyl;R.sub.2 =hydrogen, halogen or C.sub.1-4 alkoxy;R.sub.3 =hydrogen or C.sub.1-4 alkyl;R.sub.4 =C.sub.1-4 alkyl, C.sub.1-4 alkyl substituted amino, carboxylic acid substitutedC.sub.1-4 alkyl or C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkyl, or straight or branched chain C.sub.2-4 alkenyl;A=a linear C.sub.2-4 alkanediyl or alkenediyl chain, provided that A not be --CH.sub.2 CH.sub.2 -- when X is a bond; andX=a covalent bond or oxygen.Type: GrantFiled: March 8, 1995Date of Patent: July 30, 1996Assignee: Bristol-Myers Squibb Co.Inventors: Katherine S, Takaki, George N. Karageorge, Daniel J. Keavy, Michael F. Parker, Brett T. Watson
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Patent number: 5494905Abstract: 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 0-protecting group. Active compounds, in which R.sup.3 and R.sup.4 are hydrogen atoms or metabolically labile 0-protecting groups exhibit potent cell modulating effect, but minimal effect on calcium metabolism.Type: GrantFiled: May 31, 1994Date of Patent: February 27, 1996Assignee: Research Institute for Medicine and ChemistryInventors: Robert H. Hesse, Gaddam S. Reddy, Sundara K. S. Setty
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Patent number: 5492931Abstract: This invention relates to cycloalkylcarboxanilides of the formula ##STR1## in which R represents halogen or halogenoalkyl,R.sup.1 represents halogen, alkyl or halogenoalkyl,n represents the numbers 0, 1, 2 or 3,X.sup.1, X.sup.2, X.sup.3 and X.sup.4 independently of one another represent hydrogen, halogen, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio or halogenoalkylthio, andZ represents hydrogen,which have the utility as pesticides and fungicides.Type: GrantFiled: January 21, 1994Date of Patent: February 20, 1996Assignee: Bayer AktiengesellschaftInventors: Bernd-Wieland Krueger, Klaus Sasse, Thomas Schenke, Michael Negele, Heinz-Wilhelm Dehne
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Patent number: 5488131Abstract: A method for synthesizing enantiomerically enriched chemical intermediates with predetermined chirality is described. The method comprises formation of a pseudoephedrine amide, followed by stereoselective alkylation at the alpha carbon. The chiral auxiliary can then be cleaved off, affording chiral end products useful for further transformations. The enantiomeric enrichment of the chiral end products may exceed 98%, and the chiral auxiliary can be recovered. Novel amides of pseudoephedrine used in this method are also disclosed.Type: GrantFiled: March 23, 1994Date of Patent: January 30, 1996Assignee: California Institute of TechnologyInventor: Andrew G. Myers
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Patent number: 5434190Abstract: N-monosubstituted neoalkanamides of 11 to 14 carbon atoms wherein the substituent on the amide nitrogen is cyclic (aromatic or cycloaliphatic, such as aryl or cycloalkyl) and of at least five carbon atoms, have been discovered to be insect repellent, providing that any aromatic substituent is unsubstituted at the ortho position and that when the neoalkanoyl moiety is pivaloyl the total number of carbon atoms in the N-cyclic neoalkanamide is at least 12. Such neoalkanamides are useful as repellents against cockroaches, including American, German and Oriental cockroaches, and are also effective against mosquitoes (both Anopheles and Aedes), black flies and carpenter ants, and to some extent against deer ticks. They may be applied to areas, locations and items which are desirably to be kept free of such insects, with applications being direct or of solutions or emulsions thereof, preferably by spraying, or in detergent compositions or other products to be applied to such areas, etc.Type: GrantFiled: October 11, 1994Date of Patent: July 18, 1995Assignee: Colgate-Palmolive Co.Inventor: Robert J. Steltenkamp
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Patent number: 5414016Abstract: Leukotriene-B.sub.4 derivatives of formula I ##STR1## are described, in which R.sup.1 means CH.sub.2 OH, CH.sub.3, CF.sub.3, COOR.sup.5, CONR.sup.6 R.sup.7, orR.sup.1 together with R.sup.2 means a carbonyl group,R.sup.4 symbolizes H, C.sub.1 -C.sub.10 alkyl optionally substituted, C.sub.3 -C.sub.10 cycloalkyl, C.sub.6 -C.sub.10 aryl radical optionally substituted, or a 5-6-membered aromatic heterocyclic ring,A symbolizes a trans, trans-CH.dbd.CH--CH.dbd.CH, a --CH.sub.2 CH.sub.2 --CH.dbd.CH-- or a tetramethylene group,B symbolizes a C.sub.1 -C.sub.10 alkylene group, which optionally can be substituted by fluorine or the group ##STR2## D can mean a direct bond, oxygen, sulfur, --C.tbd.C--, --CH.dbd.CR.sup.6 or together withB can also mean a direct bond, their salts with physiologically compatible bases and their cyclodextrin clathrates.Type: GrantFiled: June 13, 1994Date of Patent: May 9, 1995Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Buchmann, Josef Heindl, Wolfgang Frohlich, Roland Ekerdt, Claudia Giesen
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Patent number: 5385945Abstract: Compounds of the formula ##STR1## where the dotted line represents a bond or the absence of a bond, the wavy lines represent bonds which are either in cis or trans configuration; R.sub.1 represents H, or CO--R.sub.2 where R.sub.2 is lower alkyl of 1 to 6 carbons, carbocyclic aryl or heterocyclic aryl; or carbocyclic aryl or heteroaryl substituted lower alkyl group; X represents CO--NR.sub.3 R.sub.4, CH.sub.2 OH, CH.sub.2 OR.sub.5, CH.sub.2 O--COR.sub.6, and CH.sub.2 --NR.sub.3 R.sub.4, where R.sub.3 and R.sub.4 independently are H or lower alkyl, R.sub.5 is lower alkyl of 1 to 6 carbons, and R.sub.6 is lower alkyl of 1 to 6 carbons, carbocyclic aryl or heterocyclic aryl; or carbocyclic aryl or heteroaryl substituted lower alkyl group, and n is an integer between 0 and 8 are capable of lowering intraocular pressure in the eye of a mammal.Type: GrantFiled: October 21, 1992Date of Patent: January 31, 1995Assignee: Allergan, Inc.Inventors: Michael E. Garst, Robert M. Burk
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Patent number: 5382598Abstract: Amides having formula I: ##STR1## wherein E, X, R.sup.2 and R.sup.3 have the meanings given in the specification, and pharmaceutically acceptable salts and pharmaceutically acceptable in vivo hydrolyzable esters thereof, which are useful in the treatment of urinary incontinence. Further provided are processes for preparing the amides and pharmaceutical compositions containing them.Type: GrantFiled: September 24, 1993Date of Patent: January 17, 1995Assignees: Imperial Chemical Industries PLC, Imperial Chemical HouseInventors: Russell Keith, Cyrus J. Ohnmacht, Keith H. Gibson
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Patent number: 5380925Abstract: Novel cyclic amino acids which are useful in preparing biologically active peptides as well as a process for the preparation of D and L enantiomers of the cyclic amino acids are described where an N-protected derivative of the racemic cyclic amino acid is treated with (-)cinchonidine and the resulting salt resolved into the desired enantiomers, as well as derivatives thereof and valuable intermediates used in the process.Type: GrantFiled: August 20, 1993Date of Patent: January 10, 1995Assignee: Warner-Lambert CompanyInventors: Vladimir Beylin, Huai G. Chen, Om P. Goel, Mark E. Marlatt, John G. Topliss
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Patent number: 5318994Abstract: 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: GrantFiled: November 3, 1992Date of Patent: June 7, 1994Assignee: Adir et CompagnieInventors: Jean Andrieux, Raymond Houssin, Said Yous, Beatrice Guardiola, Daniel Lesieur
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Patent number: 5290810Abstract: A compound of the formula ##STR1## in which R.sup.1 and R.sup.2 taken together represent a polymethylene chain having 3 or 4 carbon atoms, or a polymethylene chain having 3 or 4 carbon atoms substituted by at least one lower alkyl radical having 1 to 4 carbon atoms, R.sup.3 is hydrogen, hydrocarbyl or substituted hydrocarbyl and X represents cyano, a group --SO.sub.3 M or a group --S--R.sup.4 where M is hydrogen or an alkali metal such as sodium and R.sup.4 is hydrocarbyl or substituted hydrocarbyl. Typically R.sup.1 and R.sup.2 complete a cyclopentene ring, R.sup.3 is alkyl such as methyl and X is a group --SO.sub.3 Na. The compounds have microbiological activity.Type: GrantFiled: September 24, 1991Date of Patent: March 1, 1994Assignee: Imperial Chemical Industries PLCInventor: Peter W. Austin
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Patent number: 5278338Abstract: A method for racemizing an optically active carboxylic acid, or ester thereof, of the formula: ##STR1## where R.sub.1 is hydrogen, hydroxy, halo, cyano, C.sub.1 to C.sub.6 linear or branched alkoxy, amino or substituted amino or the group ##STR2## is nitrile; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched haloalkyl, aralkyl, cycloalkyl, alkyl substituted cycloalkyl, C.sub.6 to C.sub.10 aryl, C.sub.1 to C.sub.6 linear or branched alkoxy, C.sub.6 to C.sub.10 aryloxy, C.sub.1 to C.sub.6 alkylthio, C.sub.3 to C.sub.8 cycloalkylthio, C.sub.6 to C.sub.10 arylthio, C.sub.6 to C.sub.10 arylcarbonyl, C.sub.4 to C.sub.8 cycloalkenyl, trifluoromethyl, halo, C.sub.4 to C.sub.5 heteroaryl, C.sub.10 to C.sub.14 aryl, or biphenyl unsubstituted or substituted with methyl or halo, comprising heating said optically active carboxylic acid or ester thereof in the presence of water at a temperature of from about 40.degree. C.Type: GrantFiled: November 4, 1992Date of Patent: January 11, 1994Assignee: Ethyl CorporationInventor: Rhonda L. Trace
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Patent number: 5270473Abstract: This disclosure describes novel compounds, N-[(1,2,3,4,5-pentaalkyl-2,4-cyclopentadien-1-yl)methyl]-glycines, the preparation of the new compounds and their use as intermediates for the preparation of N-phosphonomethylglycine.Type: GrantFiled: February 16, 1993Date of Patent: December 14, 1993Assignee: American Cyanamid CompanyInventor: David A. Cortes
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Patent number: 5264606Abstract: A process for the preparation of monomeric polyvinyl compounds and/or oligomers thereof comprising:(i) preactivating a supported rhenium oxide catalyst with a hydrocarbyl metal compound; and(ii) reacting, under metathesis reaction conditions, norbornene or one or more substituted norbornenes, or mixtures thereof, with ethylene in the presence of the activated supported catalyst of step (i).Type: GrantFiled: November 9, 1992Date of Patent: November 23, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Kenneth G. Moloy, Bernard D. Dombek
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Patent number: 5214202Abstract: This invention relates to a synthesis method favorable for the industrial production of a benzoic acid derivative having a retinoid activity of the general formula: ##STR1## wherein the derivative can be obtained by a simple procedure in safety with high yield.Specifically, this invention relates to a synthesis method characterized in that only one vessel is needed for several reactions in the different steps of subjecting acetanilide as a starting material, which is readily available and safe to handle, to Friedel-Crafts reaction with 2,5-dimethyl-2,5-dichlorohexane; subjecting the thus obtained compound to acyl exchange reaction with monomethyl ester terephthalic chloride, followed by hydrolysis; and recrystallizing from a mixture of methanol and water.Moreover, the crystals in novel form obtained by the synthesis method of this invention are suitable for formulation, because the amount of solvents remaining therein after recrystallization is small and the grain size thereof is uniform.Type: GrantFiled: November 6, 1991Date of Patent: May 25, 1993Assignee: Shionogi & Co., Ltd.Inventors: Yoshinori Hamada, Isamu Yamada, Masaaki Uenaka, Teruo Sakata
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Patent number: 5210277Abstract: This disclosure describes novel compounds, [(1,2,3,4,5-pentaalkyl-2,4-cyclopentadien-1-yl)methyl]glycines, the preparation of the new compounds and their use as intermediates for the preparation of N-phosphonomethylglycine.Type: GrantFiled: March 12, 1992Date of Patent: May 11, 1993Assignee: American Cyanamid CompanyInventor: David A. Cortes
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Patent number: 5185465Abstract: Novel 4-phenyl-1,3-benzodiazepines and 2-amino-.alpha.-phenylphenethylamines, novel intermediates thereof, and methods of preparing same are described. These benzodiazepines are useful as antidepressants, analgetics and anticonvulsants. The 2-amino-.alpha.-phenylphenethylamines are useful as anticonvulsant and neuroprotective agents.Type: GrantFiled: October 16, 1990Date of Patent: February 9, 1993Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Lawrence L. Martin, Manfred Worm, Charles A. Crichlow
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Patent number: 5180418Abstract: Cycloalkanecarboxylic acid derivatives of formula I ##STR1## wherein W is ##STR2## and A is CO--R.sub.3 or CN; R.sub.1 is hydrogen or fluorine; R.sub.2 is halogen or cyano; R.sub.3 is chlorine, X--R.sub.5, amino, C.sub.1 -C.sub.4 alkylamino, d-C.sub.1 -C.sub.4 alkylamino, C.sub.2 -C.sub.4 haloalkylamino, di-C.sub.2 -C.sub.4 haloalkylamino, C.sub.1 -C.sub.4 hydroxyalkylamino, di-C.sub.1 -C.sub.4 hydroxyalkylamino, C.sub.3 -C.sub.4 alkenylamino, diallylamino, --N-pyrrolidino, --N-piperidino, --N-morpholino, --N-thiomorpholino, --N-piperidazino, the group --O--N.dbd.C--(R.sub.9)R.sub.10 or the group --N--R.sub.6 (OR.sub.6); each of R.sub.4 and R.sub.14, independently of the other, is hydrogen, fluorine, chlorine, bromine, C.sub.1 -C.sub.4 alkyl or trifluoromethyl; R.sub.5 is hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.10 alkylthio-C.sub.1 -C.sub.4 alkyl, di-C.sub.1 -C.sub.4 alkylamino-C.sub.1 -C.sub.4 alkyl, cyano-C.sub.1 -C.sub.Type: GrantFiled: July 19, 1991Date of Patent: January 19, 1993Assignee: Ciba-Geigy CorporationInventors: Georg Pissiotas, Hans Moser, Hans-Georg Brunner, Eginhard Steiner
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Patent number: 5153212Abstract: 2-adamantyl-4-isothiazoline-3-one has the formula ##STR1## wherein R.sub.1 and R.sub.2, each independently, represent hydrogen or halogen,or R.sub.1 and R.sub.2, taken together, form a polymethylene chain having 3-4 carbon atoms, optionally substituted by lower alkyl or halogen,or R.sub.1 and R.sub.2, taken together, form a pyridine ring with the double bond of the 4-isothiazoline-3-one ring andAda represents 1'-adamantyl, 2'-adamantyl or 1'-adamantyl methyl, and its mineral or organic acid salt.The compound is useful as an antibacteria, antialgae or antifungus agent in various industrial fields.Type: GrantFiled: June 3, 1991Date of Patent: October 6, 1992Assignee: Centre International de Recherches Dermatoglogiques (C.I.R.D.)Inventors: Braham Shroot, Jean Maignan, Rainer Schmidt
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Patent number: 5122361Abstract: Novel CNS dopamine D-2 receptors, such as the compound 5-iodo-7-N-[(1-ethyl-2-pyrrolidinyl)methyl]carboxamide-2,3-dihydrobenzofur an, are disclosed. These compounds are useful as imaging agents for D-2 receptors in the human brain and exhibit good brain retention and in vivo stability.Type: GrantFiled: April 17, 1989Date of Patent: June 16, 1992Assignee: Trustees of the University of PennsylvaniaInventors: Hank F. Kung, Raymond Murphy
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Patent number: 5120871Abstract: This disclosure describes novel compounds, N-[(1,2,3,4,5-pentaalkyl-2,4-cyclopentadien-1-yl)methyl]-glycines, the preparation of the new compounds and their use as intermediates for the preparation of N-phosphonomethylglycine.Type: GrantFiled: May 16, 1991Date of Patent: June 9, 1992Assignee: American Cyanamid CompanyInventor: David A. Cortes
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Patent number: 5089639Abstract: N-Cycloalkylalkylamines of formula I: ##STR1## in which: R1 is phenyl which is optionally mono-, di- or trisubstituted by halogens or lower alkyl, haloalkyl or lower alkoxy radicals, or is an aromatic heterocyclic radical having 5 to 7 chain members, in which the hetero atom is nitrogen, oxygen or sulphur,R2 is lower alkyl,R3 is hydrogen or lower alkyl,m has the value of 1 or 2,R4 is cycloalkyl --CH(CH2)n, in which a carbon atom may carry a radical Rx, which is lower alkyl or phenyl; and in which n has the values from 2 to 5,R5 is phenyl, which can be mono-, di- or trisubstituted by halogens or by lower alkoxy radicals, andQ represents an ethylene-1,2-diyl group --CH.dbd.Type: GrantFiled: January 24, 1991Date of Patent: February 18, 1992Assignee: Jouveinal S.A.Inventors: Gilbert G. Aubard, Alain P. Calvet, Jean-Pierre Defaux, Claude J. Gouret, Agnes M. Grouhel, Henry L. Jacobelli, Jean-Louis Junien, Xavier B. Pascaud, Francois F. Roman, James P. Hudspeth, Yuan Lin
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Patent number: 5081284Abstract: A novel N-substituted peptidyl compound represented by the general formula (1): ##STR1## where R.sub.1 is a straight-chained or branched acyl group having 2-10 carbon atoms, a branched, cyclic or partly branched cyclic alkyloxycarbonyl group having 4-15 carbon atoms, a substituted or unsubstituted benzyloxycarbonyl group, a 2,2,2-trichloroethyloxycarbonyl group, a 2-(trimethylsilyl)ethyloxycarbonyl group, a p-toluensulfonyl group, an o-nitrophenylsulfenyl group, a diphenylphosphonothioyl group, a triphenylmethyl group, a 2-benzoyl-1-methylvinyl group or a 4-phenylbutyryl group; R.sub.2 is a hydrogen atom or when taken together with R.sub.1, may form a phthaloyl group; R.sub.3 is an isobutyl group, a n-butyl group or an isopropyl group; R.sub.4 is a butyl group, a benzyl group or a methylthioethyl group; and R.sub.5 is a hydrogen atom or a chloromethyl group, which inhibits the activity of cysteine proteinases.Type: GrantFiled: June 29, 1989Date of Patent: January 14, 1992Assignee: Suntory LimitedInventors: Naoki Higuchi, Masayuki Saitoh, Norio Iwasawa, Motoo Sumida, Hiroshi Shibata
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Patent number: 5071875Abstract: The present invention relates generally to compounds having melatonin receptor activities and in particular to substituted 2-amidotetralin derivatives; to pharmaceutical preparations comprising such compounds; and to methods for using these compounds as therapeutic and diagnostic reagents.Type: GrantFiled: September 25, 1989Date of Patent: December 10, 1991Assignee: Northwestern UniversityInventors: Alan S. Horn, Margarita L. Dubocovich
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Patent number: 5064827Abstract: Compounds of the present invention, are represented by the general formula ##STR1## wherein R.sub.1 group which may be alkyl of from 1 to about 6 carbon atoms, alkenyl of from 2 to about 6 carbon atoms, alkynyl of from 2 to about 10 carbon atoms, alkoxy wherein the alkyl group contains from 1 to about 6 carbon atoms, halogen, acetamido, amino, nitro, alkylamino of from 1 to about 6 carbon atoms, hydroxy, hydroxyalkyl of from 1 to about 6 carbon atoms, cyano or arylalkoxy wherein the alkyl group contains from 1 to about 6 carbon atoms R.sub.2, R.sub.3 and R.sub.4 are hydrogen or hydroxyl groups or the combination of either hydrogen or hydroxyl groups; W represents alkylene of from 1 to about 10 carbon atoms; and B represents --NHCOR.sub.5, --NHCONR.sub.5 R.sub.6, or --NHCOOR.sub.5 wherein R.sub.5 and R.sub.Type: GrantFiled: August 23, 1990Date of Patent: November 12, 1991Assignee: Du Pont Merck Pharmaceutical CompanyInventors: Ghanshyam Patil, William L. Matier, Khuong H. X. Mai
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Patent number: 5059623Abstract: A substituted cycloalkyl- or heterocyclyl-carboxanilide of the formula (I) ##STR1## in which X stands for an unsubstituted or an alkyl-substituted cycloalkyl or an unsubstituted or an alkyl-substituted heterocyclic,Hal stands for halogen andY.sup.1, Y.sup.2 and Y.sup.3 independently of one another stand for hydrogen, halogen, an unsubstituted or a halogen-substituted alkyl, an unsubstituted or a halogen-substituted alkoxy or an unsubstituted or a halogen-substituted alkylthio. Such substituted cycloalkyl- or heterocyclyl-carboxanilides are useful as fungicides.Type: GrantFiled: April 5, 1989Date of Patent: October 22, 1991Assignee: Bayer AktiengesellschaftInventors: Bernd-Wieland Kruger, Klaus Sasse, Hermann Hagemann, Albrecht Marhold, Wilhelm Brandes
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Patent number: 5059620Abstract: The present invention relates to new compounds of the formula ##STR1## wherein X is ##STR2## wherein R.sub.1 is hydrogen, lower alkyl, phenyl, benzyl, cinnamoyl, thiophene, furan, pyrrole, imidazole, pyrazole oxazole or thiazole; W is hydrogen or hydroxy; (Y).sub.A is positioned ortho to W and is an aminoloweralkyl having the formula --CH.sub.2 NR.sub.2 R.sub.3 where R.sub.2 and R.sub.3 are the same or different and may be lower alkyl or R.sub.2 and R.sub.3 may together with N form a pyrrolidine, piperidine or azepine ring, and A is 2; n and m are independently from 0 to 5; and R is straight or branched C.sub.1 -C.sub.10 alkyl, straight or branched C.sub.3 -C.sub.10 cycloalkyl, straight or branched C.sub.2 -C.sub.4 alkenyl or straight or branched C.sub.2 -C.sub.4 alkynyl, or a pharmaceutically acceptable salt thereof.These compounds are useful in the treatment of various cardiac arrhythmias.Type: GrantFiled: April 7, 1988Date of Patent: October 22, 1991Assignee: The Du Pont Merck Pharmaceutical CompanyInventors: David M. Stout, William L. Matier, Lawrence A. Black
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Patent number: 5034419Abstract: N-Cycloalkylalkylamines of formula I: ##STR1## in which: R1 is phenyl which is optionally mono-, di- or trisubstituted by halogens or lower alkyl, haloalkyl or lower alkoxy radicals, or is an aromatic heterocyclic radical having 5 to 7 chain members, in which the hetero atom is nitrogen, oxygen or sulphur,R2 is lower alkyl,R3 is hydrogen or lower alkyl,m has the value of 1 or 2,R4 is cycloalkyl --CH(CH2)n, in which a carbon atom may carry a radical Rx, which is lower alkyl or phenyl; and in which n has the values from 2 to 5,R5 is phenyl, which can be mono-, di- or trisubstituted by halogens or by lower alkoxy radicals, andQ represents an ethylene-1,2-diyl group --CH.dbd.Type: GrantFiled: February 26, 1990Date of Patent: July 23, 1991Assignee: L'OrealInventors: Gilbert G. Aubard, Alain P. Calvet, Jean-Pierre DeFaux, Claude J. Gouret, Agnes M. Grouhel, Henry L. Jacobelli, Jean-Louis Junien, Xavier Pascaud, Francois F. Roman, James P. Hudspeth, Yuan Lin
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Patent number: 5001261Abstract: Cyclohexenone derivatives of the formula ##STR1## where R.sup.1, R.sup.2 R.sup.3, R.sup.4 and R.sup.5 have the meanings given in the disclosure, and their use for controlling unwanted plant growth.Type: GrantFiled: April 18, 1988Date of Patent: March 19, 1991Assignee: BASF AktiengesellschaftInventors: Michael Keil, Rainer Becker, Dieter Jahn, Norbert Goetz, Ulrich Schirmer, Bruno Wuerzer
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Patent number: 4992588Abstract: O-acrylaminomethylbenzyl halides (I) ##STR1## in which X is Cl or Br and R.sup.1 is alkyl or aryl, are obtained by reacting an o-aminomethylbenzyl alkyl ether (II) ##STR2## with an acylating agent, and then reacting the resulting acid amide, preferably without intermediate isolation, with an aqueous hydrohalic acid.Type: GrantFiled: July 31, 1985Date of Patent: February 12, 1991Assignee: BASF AktiengesellschaftInventors: Josef Mueller, Walter-Weilant Wiersdorff, Werner Kirschenlohr, Gerd Schwantje
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Patent number: 4983629Abstract: 11-Haloprostane derivatives of general Formula I ##STR1## wherein X is F, Cl or Br,R.sub.1 is the residue CH.sub.2 OH or ##STR2## wherein R.sub.2 means a hydrogen atom, an alkyl, cycloalkyl, aryl, phenacyl or heterocyclic residue,A is a --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH--group,B is a --CH.sub.2 --CH.sub.2 -- or trans--CH.dbd.CH-- or a --C.tbd.C--group,W is an ethylenedioxymethylene group or a hydroxymethylene group,D and E together mean a direct bond orD is a C.sub.1-10 -alkylene group,E is an oxygen or sulfur atom, a direct bond, a --C.tbd.C--bond or a --CR.sub.6 .dbd.CR.sub.7 -group with R.sub.6 and R.sub.7 meaning a hydrogen atom, a chlorine atom or an alkyl group,R.sub.4 is a hydroxy group,R.sub.5 is a hydrogen atom, an alkyl, a cycloalkyl, an aryl or a heterocyclic group, andthe salts thereof with physiologically compatible bases, processes for their preparation, and use thereof as agents inhibiting gastric acid secretion.Type: GrantFiled: June 21, 1989Date of Patent: January 8, 1991Assignee: Schering AktiengesellschaftInventors: Helmut Vorbruggen, Norbert Schwarz, Olaf Loge, Claus-Steffen Sturzebecher, Walter Elger
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Patent number: 4981872Abstract: Prostaglandin derivatives having an oxo group at specified positions in the .alpha. side chain have a variety of physiological effects, notably a strong anti-ulcer activity accompanied by a limited ability to inhibit blood platelet aggregation.Type: GrantFiled: January 15, 1988Date of Patent: January 1, 1991Assignee: Sankyo Company LimitedInventors: Koichi Kojima, Shigeo Amemiya, Kazuo Koyama, Keiichi Tabata, Nobuyoshi Iwata
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Patent number: 4931591Abstract: Compounds of the formula ##STR1## in which R.sub.1 represents hydrogen or acyl, A represents an optionally N-alkylated .alpha.-amino acid residue which is bonded N-terminally to R.sub.1 and C-terminally to the group --NR.sub.2 --, R.sub.2 represents hydrogen or lower alkyl, R.sub.3 represents hydrogen, lower alkyl, optionally etherified or esterified hydroxy-lower alkyl, cycloalkyl, cycloalkyl-lower alkyl, bicycloalkyl-lower alkyl, tricycloalkyl-lower alkyl, aryl or aryl-lower alkyl, R.sub.4 represents hydroxy or etherified or esterified hydroxy, R.sub.5 represents lower alkyl having 2 or more carbon atoms, optionally etherified or esterified hydroxy-lower alkyl, cycloalkyl, cycloalkyl-lower alkyl, bicycloalkyl, bicycloalkyl-lower alkyl, tricycloalkyl, tricycloalkyl-lower alkyl, aryl, aryl-lower alkyl, optionally substituted carbamoyl, optionally substituted amino, optionally substituted hydroxy or optionally substituted mercapto and R.sub.Type: GrantFiled: July 12, 1989Date of Patent: June 5, 1990Assignee: Ciba-Geigy CorporationInventors: Peter Buhlmayer, Vittorio Rasetti, Walter Fuhrer, James L. Stanton, Richard Goschl
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Patent number: 4898977Abstract: The invention relates to novel processes and intermediates for the preparation of 5-amino-4-hydroxyvaleric acid derivatives of the formula ##STR1## in which R.sup.1 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl or the radical of a natural amino acid, R.sup.2 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl, amino, hydroxy, mercapto, sulphinyl, sulphonyl or the radical of a natural amino acid, and R.sup.3 represents optionally substituted hydroxy or amino, by sigmatropic rearrangement of a suitable allyl ester, halolactonisation of the resulting .gamma.,.delta.-unsaturated acid or of a suitable derivative thereof, exchange of halogen for a nitrogen-containing nucleophile, opening of the lactone ring and freeing of the amino group. Compounds of the formula I are starting materials for the preparation of renin-inhibitors which have an anti-hypertensive action.Type: GrantFiled: August 13, 1987Date of Patent: February 6, 1990Assignee: Ciba-Geigy CorporationInventors: Peter Herold, Christof Angst