Oxy In Acid Moiety Patents (Class 560/39)
-
Patent number: 5374656Abstract: This invention relates to compounds of formula: ##STR1## in which R.sub.1 represents a hydrogen atom or an alkyl or alkoxycarbonyl radical or an unsubstituted or substituted phenyl radical,R.sub.2 represents an alkyl (1-8 C) or polyfluoroalkyl radical or an unsubstituted or substituted cycloalkyl radical,R.sub.3 represents an unsubstituted or substituted phenyl radical, a naphthyl, indolyl, quinolyl or phenylamino radical in which the phenyl ring is optionally substituted, or a quinolylamino radical, andm is 0 or 1, the process for preparing them and the medicaments containing them.Type: GrantFiled: June 25, 1992Date of Patent: December 20, 1994Assignee: Rhone-Poulenc Rorer, S.A.Inventors: Jean-Dominique Bourzat, Marc Capet, Claude Cotrel, Claude Guyon, Franco Manfre, Gerard Roussel
-
Patent number: 5374765Abstract: Disclosed is a method for extracting an amino acid ester from a hydrous solution which comprises adding thereto a water-insoluble organic solvent and then an amount of a base effective to liberate only a portion of the amino acid ester in free base form, and transferring the thus liberated amino acid ester in the free base form into the organic layer, and repeating the neutralization-extraction steps until all of the amino acid ester has been extracted.Type: GrantFiled: January 19, 1993Date of Patent: December 20, 1994Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Tomoko Kamashita, Hiroyuki Yamashita, Teruyuki Nagata, Masanobu Ajioka
-
Patent number: 5364850Abstract: The present invention provides substituted tyrosyl diamide compounds of general Formula I: ##STR1## and the pharmaceutically-acceptable salts thereof, which are useful for inducing analgesia in animals, pharmaceutical compositions comprising a pharmaceutically-acceptable carrier and a compound of Formula I, and a method for inducing analgesia in an animal in need thereof comprising administering a therapeutically-effective amount of a compound of Formula I to the animal.Type: GrantFiled: September 24, 1993Date of Patent: November 15, 1994Assignee: G. D. Searle & Co.Inventors: Donald W. Hansen, Jr., Nizal S. Chandrakumar, Karen B. Peterson, Sofya Tsymbalov, Robert K. Husa
-
Patent number: 5364961Abstract: The invention includes selected novel optically active .alpha.-amino ketones which either are themselves useful or are intermediates for the preparation of known ketomethylene pseudopeptides useful as antibiotics, antibiotic enhancers, or enzyme inhibitors. Further, the present invention provides a method for dehydrogenation/asymmetrical hydrogenation to obtain essentially pure antipodes of ketomethylene pseudopeptides having two chiral centers.Type: GrantFiled: June 15, 1992Date of Patent: November 15, 1994Assignee: Monsanto CompanyInventor: John J. Talley
-
Patent number: 5362902Abstract: Compounds of formula (I) are diuretic agents for treating various cardiovascular diseases including hypertension, heart failure and renal insufficiency.Type: GrantFiled: July 21, 1992Date of Patent: November 8, 1994Assignee: Pfizer Inc.Inventors: Ian T. Barnish, Keith James
-
Patent number: 5359123Abstract: Trifunctional polyoxyalkylene polyamines having a plurality of 2-alkoxycarbonylethylamino groups at terminals are produced by reacting the corresponding primary amines with an alkyl acrylate. The trifunction secondary polyamines thus produced have a moderate reaction rate with a polyisocyanate component in polyurea RIM.Type: GrantFiled: March 29, 1993Date of Patent: October 25, 1994Assignee: Nippon Paint Co., Ltd.Inventors: Toshiyuki Ohshima, Hideo Ishibashi, Rie Tamura, Satoshi Yamamoto, Takaharu Izumo
-
Patent number: 5354892Abstract: The invention relates to biaryl substituted 4-amino-butyric acid derivatives of formula I ##STR1## wherein COX and COX' independently represent carboxyl or carboxyl derivatized in form of a pharmaceutically acceptable ester or amide; R.sub.1 represents hydrogen, lower alkyl, C.sub.3 -C.sub.7 -cycloalkyl-lower alkyl, aryl-lower alkyl, biaryl-lower alkyl, lower alkoxy, aryl-lower alkoxy, aryloxy, N-lower alkylamino, N,N-di-lower alkylamino, N-aryl-lower alkylamino, N,N-di-aryl-lower alkylamino, N-arylamino, N,N-diarylamino, lower alkanoylamino, aryl-lower alkanoylamino or aroylamino; R.sub.2 represents hydrogen, hydroxy, lower alkoxy, lower alkyl, aryl-lower alkyl, C.sub.3 -C.sub.Type: GrantFiled: January 25, 1993Date of Patent: October 11, 1994Assignee: Ciba-Geigy CorporationInventor: Gary Ksander
-
Patent number: 5354884Abstract: .alpha.-Fluoro-substituted N-acryloylamino acid derivatives of the formula ##STR1## are used to make polymers optionally for chromatographic resolution of racemates into their enantiomers. The fluorine atom improves performance in many instances.Type: GrantFiled: October 1, 1992Date of Patent: October 11, 1994Assignee: Bayer AktiengesellschaftInventors: Rolf Grosser, Walter Lange, Bruno Bomer, Dieter Arlt, Dietmar Bielefeldt
-
Patent number: 5336800Abstract: Oxamides useful as dye intermediates have the formula ##STR1## where R.sup.1 and R.sup.2 are independently of each other hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,X is hydroxyl, nitro or a radical of the formula --NR.sup.3 R.sup.4, where R.sup.3 is hydrogen or C.sub.1 -C.sub.4 -alkanoyl and R.sup.4 is hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,Z is C.sub.2 -C.sub.8 -alkylene, substituted or unsubstituted phenylene or substituted or unsubstituted naphthylene, or X--Z and R.sup.1 are, together with the nitrogen atom joining them together, the radical of the formula ##STR2## where R.sup.3 is as defined above,L is a bridge member andY is vinyl or a radical of the formula --C.sub.2 H.sub.4 --A, where A is hydroxyl or a group which is detachable under alkaline reaction conditions.Type: GrantFiled: January 4, 1993Date of Patent: August 9, 1994Assignee: BASF AktiengesellschaftInventors: Bernd Siegel, Manfred Patsch, Knut Kessel
-
Patent number: 5336805Abstract: Process for preparing an a-amino acid having the general formula (1) of ##STR1## where R represents an aryl group or a substituted aryl, cycloalkyl or alkyl group, in which process glyoxylic acid, or a precursor or derivative thereof, is contacted in the presence of sulphamic acid with an unsaturated compound chosen from the group of aromatics, cycloalkenes and alkenes. By applying the process higher efficiencies are obtained.The acid obtained as reaction product can be esterified and amidated without prior isolation.Type: GrantFiled: August 12, 1992Date of Patent: August 9, 1994Assignee: DSM N.V.Inventors: Wilhelmus H. J. Boesten, Nicolaas A. de Heij
-
Patent number: 5331007Abstract: There is provided a method of treatment of neurological disorders, such as epilepsy, stroke and cerebral ischaemia, which comprises the administration of a compound of Formula I: ##STR1## wherein, Ar.sub.1 and Ar.sub.2, which may be the same or different, independently represent phenyl or phenyl substituted by one or more of amino, nitro, halogen, hydroxy, C1 to 6 alkoxy, C1 to 6 alkyl or cyano;R.sub.1 represents hydrogen, C1 to 6 alkyl, C1 to 6 alkoxycarbonyl;R.sub.2 represents hydrogen or COCH.sub.2 NH.sub.2 ;R.sub.3 represents hydrogen or C1 to 6 alkyl;in addition, when R.sub.2 represents hydrogen either one or both of Ar.sub.1 and Ar.sub.2 may also represent 2-, 3- or 4-pyridinyl and R.sub.1 may also represent trihalomethyl;or a pharmaceutically acceptable salt thereof.Some of the compounds of formula I are novel, and these are also provided, together with pharmaceutical compositions containing the novel compounds.Type: GrantFiled: July 20, 1992Date of Patent: July 19, 1994Assignee: Fisons CorporationInventors: Ronald C. Griffith, James J. Napier
-
Patent number: 5328909Abstract: A novel cyclopropenone derivative (I) which possesses a potent inhibitory activity against thiol protease such as papain, cathepsin B, cathepsin H, cathepsin L, calpain or the like with excellent properties regarding oral absorbance, tissue transference and cell membrane permeability, and are clinically useful in the treatment of various diseases such as muscular dystrophy, amyotrophy. Also provided are a process for producing the compound (I) and a pharmaceutical composition containing the same.Type: GrantFiled: June 25, 1992Date of Patent: July 12, 1994Assignee: Mitsubishi Kasei CorporationInventors: Ryoichi Ando, Yasuhiro Morinaka, Chizuko Takahashi, Yoshikuni Tamao, Akihiro Tobe
-
Patent number: 5324833Abstract: Compounds of the formula I, ##STR1## in which 'R.sub.1 is an amino protective group, and n stands for 1 or 2, R.sub.1 denotes hydrogen or an amino protective group, R.sub.2 denotes hydrogen or a carboxyl protective group and R.sub.3 denotes triphenylmethyl, 4-monomethoxy-trityl or 4,4'-dimethoxy-trityl, and reactive carboxylic acid derivatives of such compounds of the formula I in which R.sub.2 stands for hydrogen, are described.These compounds can be used as starting materials for the preparation of peptides. They are more suitable for this than are analogous compounds of the formula I in which R.sub.3 denotes hydrogen or one of the carbamoyl protective groups hitherto customary.Type: GrantFiled: April 13, 1990Date of Patent: June 28, 1994Assignee: Novabiochem AGInventors: Peter Sieber, Bernhard Riniker
-
Patent number: 5321150Abstract: 5-Deaza-10-oxo- and 5-deaza-10-thio-5,6,7,8-tetrahydrofolic acid derivatives are provided as agents useful for treating susceptible neoplasms in mammals. Pharmaceutical formulations and intermediates are also provided.Type: GrantFiled: July 7, 1992Date of Patent: June 14, 1994Assignee: Eli Lilly and CompanyInventors: Homer L. Pearce, Mark A. Winter
-
Patent number: 5304670Abstract: Process for the enantioselective preparation of phenylisoserine derivatives of general formula (I), in which R represents a phenyl or tert-butoxy radical, R.sub.1 represents a hydrogen atom or an alkyl radical containing 1 to 4 carbon atoms and R.sub.2 represents a hydrogen atom or a group protecting the alcohol function.Type: GrantFiled: January 15, 1993Date of Patent: April 19, 1994Assignee: Centre National de la Recherche ScientifiqueInventors: Arlene G. Correa, Jean-Noel Denis, Andrew E. Greene
-
Patent number: 5300640Abstract: A novel herbicidal pyrimidine derivative represented by the formula ##STR1## wherein each of R.sup.1, R.sup.2, R.sup.3, R.sup.4, Y.sup.1, Y.sup.2, Y.sup.3, X and Z are as defined herein.Type: GrantFiled: December 19, 1991Date of Patent: April 5, 1994Assignee: Sumitomo Chemical Company, LimitedInventors: Mitsumori Hiratsuka, Naonori Hirata, Kazuo Saito, Hideyuki Shibata
-
Patent number: 5298647Abstract: Aromatic compounds absorbing UVB and/or UVA, substituted with an amide function, selected from the group consisting of ##STR1## whose variable substituents are as defined in the specification, e.g. ##STR2## are useful as photoprotective agents or tanning accelerators.Type: GrantFiled: December 14, 1987Date of Patent: March 29, 1994Inventors: Dominique Robert, Louis Jung
-
Patent number: 5298652Abstract: Compounds of the formula ##STR1## R is hydrogen or --CH.sub.2 COOH; m is 0-2,x is 1-2, with the provision that when x is 2, m is always 0;R.sub.1 is CH.sub.3 (CH.sub.2).sub.n O--, CH.sub.3 (CH.sub.2).sub.n CONH--, CH.sub.3 (CH.sub.2).sub.n NHCONH--, CH.sub.3 (CH.sub.2).sub.n NHCOO--, HOOC(CH.sub.2).sub.p O-- or R.sub.3 (CH.sub.2).sub.q O--;R.sub.2 is hydrogen, carboxy, hydroxy, nitro, amino, CH.sub.3 (CH.sub.2).sub.n O--, CH.sub.3 (CH.sub.2).sub.n CONH--, CH.sub.3 (CH.sub.2).sub.n NHCONH--, CH.sub.3 (CH.sub.2).sub.n NHCOO--, HOOC(CH.sub.2).sub.p O--, R.sub.3 (CH.sub.2).sub.q O-- or R.sub.4 [O(CH.sub.2).sub.2 ].sub.r O--,wherein n is 0-17, p is 1-10, q is 1-12, r is 1-6,R.sub.3 is 1- or 2- naphthyloxy, 2,3- or 3,4-dihydroxyphenyl, phenyl, phenoxy or substituted phenyl or phenoxy, wherein the substituent is selected from the group consisting of lower alkyl, lower alkoxy, hydroxy, nitro, amino, halo, carboxy or phenyl, andR.sub.4 is lower alkyl;and pharmaceutically acceptable salts with bases,are described.Type: GrantFiled: December 8, 1992Date of Patent: March 29, 1994Assignee: Hoffmann-La Roche Inc.Inventors: Mathew Carson, Ru-Jen L. Han, Ronald A. LeMahieu, Vincent S. Madison
-
Patent number: 5294643Abstract: Novel cinnamamide derivatives and the salts thereof are provided. An antihyperlipidemic composition is also provided. The composition comprises an active ingredient which is at least one selected from the group consisting of the above-mentioned cinnamamide derivative and the pharmaceutically acceptable salt thereof.Type: GrantFiled: July 5, 1990Date of Patent: March 15, 1994Assignee: Kanegafuchi Kagaku Kogyo KabushikiInventors: Yoshihide Fuse, Kenji Fujii, Keiji Kameyama, Taizo Kawabe, Toshiaki Miwa, Ikuo Katsumi
-
Patent number: 5294734Abstract: Substituted 2-aminoalk-3-enoic acid derivative of formula I ##STR1## wherein R.sub.1 is an aliphatic hydrocarbon radical that is substituted by optionally acylated or aliphatically or araliphatically etherified hydroxy, by halogen, by optionally acylated and/or aliphatically substituted amino or by an aza-, diaza-, azoxa- or oxa-cycloaliphatic radical, or is an oxacycloaliphatic hydrocarbon radical bonded via a carbon atom, or is an optionally aliphatically N-substituted or N-acylated azacycloaliphatic hydrocarbon radical, and R.sub.2 is free or esterified carboxy, and their salts exhibit NMDA-antagonistic properties and are useful as active ingredients of anticonvulsive medicaments.Type: GrantFiled: March 16, 1992Date of Patent: March 15, 1994Assignee: Ciba-Geigy Corp.Inventors: Christof Angst, Hans Allgeier, Roland Heckendorn, Daniel Wallach
-
Patent number: 5292924Abstract: .alpha.-Fluoro-substituted N-acryloylamino acid derivatives of the formula ##STR1## are used to make polymers optionally for chromatographic resolution of racemates into their enantiomers. The fluorine atom improves performance in many instances.Type: GrantFiled: November 13, 1992Date of Patent: March 8, 1994Assignee: Bayer AktiengesellschaftInventors: Rolf Grosser, Walter Lange, Bruno Bomer, Dieter Arlt, Dietmar Bielefeldt
-
Patent number: 5274188Abstract: The invention relates to a novel process for the manufacture of (3R,1'R)-4-acyloxy-3-(1'-hydroxyethyl)-2-azetidinones of formula ##STR1## in which R.sup.1 represents lower alkyl or aryl, by enantioselective reduction of the carbonyl group in a suitable .alpha.-acylaminomethyl-acetoacetic acid ester, cyclisation of the resulting .alpha.-acylaminomethyl-.beta.-hydroxybutyric acid ester to a 5,6-dihydro-1,3,4H-oxazine with inversion of the carbon atom carrying the hydroxy group, equilibration to form the preferred trans-substituted dihydrooxazine, recleaving to form the configuratively uniform .alpha.-aminomethyl-.beta.-hydroxybutyric acid, ring-closure to form the .beta.-lactam and oxidative acylation at C(4) of the .beta.-lactam. Compounds of formula I can be used as starting materials for the manufacture of .beta.-lactam antibiotics. The invention relates also to novel intermediates.Type: GrantFiled: August 6, 1991Date of Patent: December 28, 1993Assignee: Ciba-Geigy CorporationInventors: Peter Schneider, Gerardo Ramos
-
Patent number: 5274002Abstract: Novel trisubstituted phenyl analogs are now found to have activity as for the treatment of congestive heart failure.Type: GrantFiled: September 6, 1990Date of Patent: December 28, 1993Assignee: Warner-Lambert CompanyInventor: Lynn D. Hawkins
-
Patent number: 5272175Abstract: The present invention provides substituted tyrosyl diamide compounds of general Formula I: ##STR1## and the pharmaceutically-acceptable salts thereof, which are useful for inducing analgesia in animals, pharmaceutical compositions comprising a pharmaceutically-acceptable carrier and a compound of Formula I, and a method for inducing analgesia in an animal in need thereof comprising administering a therapeutically-effective amount of a compound of Formula I to the animal.Type: GrantFiled: May 20, 1992Date of Patent: December 21, 1993Assignee: G. D. Searle & Co.Inventors: Donald W. Hansen, Jr., Nizal S. Chandrakumar, Karen B. Peterson, Sofya Tsymbalov, Robert K. Husa
-
Patent number: 5256806Abstract: Novel intermediates useful in the preparation of the optically active antiviral compound [1R-(1.alpha.,2.beta.,3.alpha.)]-2-amino-9-[2,3-bis(hydroxymethyl)cyclobut yl]-1,9-dihydro-6H-purin-6-one are described.Type: GrantFiled: November 12, 1992Date of Patent: October 26, 1993Assignee: E. R. Squibb & Sons, Inc.Inventors: Gregory S. Bisacchi, Toomas Mitt
-
Patent number: 5254730Abstract: Amino acids and amino acid derivatives bearing isotopic hydrogen labels at both the .alpha.- and .beta.-positions are produced when N-substituted azomethine derivatives of carboxylic acids and carboxylic acid derivatives are hydrogenated over metal catalysts in isotopically-enriched protic solvents with molecular hydrogen.Type: GrantFiled: January 14, 1992Date of Patent: October 19, 1993Inventor: James L. Kilgore
-
Patent number: 5254725Abstract: The present invention provides inhibitors of kynureninase having the formula ##STR1## where R.sub.a and R.sub.b, independently of one another are H, a halogen, CF.sub.3 or a small alkyl group having one to three carbon atoms; R.sub.1 is NH.sub.2, NR.sub.6 R.sub.7, halogen, CF.sub.3 or a small alkyl group having from one to three carbon atoms, wherein R.sub.6 and R.sub.7, independently of one another, are H, a formyl group or a small alkyl group having from one to three carbon atoms with the exception that only one of R.sub.6 or R.sub.7 can be a formyl group; R.sub.2 is OH, H, halogen, CF.sub.3 or a small alkyl group having from one to three carbon atoms; and R.sub.3, R.sub.4 and R.sub.5, independently of one another, are H, halogen, CF.sub.3 or small alkyl group having from one to three carbon atoms. In particular, compounds of formula I having the (.alpha.S,.gamma.S) configuration or (.alpha.R,.gamma.R) configuration when R.sub.A or R.sub.B is a halogen are more potent inhibitors of kynureninase.Type: GrantFiled: April 18, 1991Date of Patent: October 19, 1993Assignee: University of Georgia Research Foundation, Inc.Inventors: Robert S. Phillips, Rajesh K. Dua
-
Patent number: 5252745Abstract: Antimicrobial compounds of the formula ##STR1## wherein R.sup.1 is selected from the group consisting of H, an amine protective group, and a moiety of the formula ##STR2## wherein R.sup.2, R.sup.5, and R.sup.6 are independently selected from H and an amine protective group;R.sup.3 and R.sup.4 are independently selected from H, lower alkyl, aryl, arylalkyl, CH.sub.2 OR, CH.sub.2 SR or CH(CH.sub.3)OR;R=H, propargyl lower alkyl, arylalkyl or aryl;wherein R.sup.1 and R.sup.2 or R.sup.5 and R.sup.6 can be joined to form a ring; and wherein when R.sup.1 and R.sup.2 or R.sup.5 and R.sup.6 are both H, the compound is either in free base form or in salt form.Type: GrantFiled: May 21, 1991Date of Patent: October 12, 1993Assignee: Rohm and Haas CompanyInventors: Margaret M. Bowers-Daines, Barry C. Lange
-
Patent number: 5248813Abstract: A process for obtaining a substantially pure enantiomer of an aryl-substituted aliphatic carboxylic acid is described. The process utilizes first an enantiomerically enriched mixture the of aryl-substituted aliphatic carboxylic acid obtained from kinetic resolution, diastereomeric crystallization or asymmetric synthesis processes. This enriched mixture is reacted with a base producing a salt that has the following properties:(1) has at least one eutectic point;(2) a composition that is not at the eutectic point; and(3) a eutectic composition that is closer to the racemic composition than is the eutectic composition of said aryl-substituted carboxylic acid.Substantially pure, enantiomeric salt is separated, leaving a mother liquor comprising the solvent and aryl-substituted aliphatic carboxylic acid enriched in the other enantiomer.Type: GrantFiled: October 14, 1992Date of Patent: September 28, 1993Assignee: Ethyl CorporationInventors: Thanikavelu Manimaran, G. Patrick Stahly, R. Carl Herndon, Jr.
-
Patent number: 5231216Abstract: There are described novel trans-2-acylaminocyclohexyloxyacyldipeptides of formula I ##STR1## wherein R.sub.1 represents --CO--R.sub.6, --SO.sub.2 --R.sub.7 or ##STR2## R.sub.6 is C.sub.1 -C.sub.18 alkyl or C.sub.1 -C.sub.18 alkoxy, R.sub.7 is C.sub.1 -C.sub.18 alkyl or an optionally substituted phenyl group,Y is .dbd.O, .dbd.S or .dbd.NH;R.sub.2 =R.sub.3 and represent --H or C.sub.1 -C.sub.12 alkyl,R.sub.4 represents --OR.sub.8 or --NHR.sub.9,R.sub.8 is --H, C.sub.1 -C.sub.8 alkyl or benzyl,R.sub.9 is --H, a straight or branched chain C.sub.1 -C.sub.18 alkyl group or benzyl group;R.sub.5 represents --OR.sub.9 or --NHR.sub.9,and novel (1R,2R)- and (1S,2S)-trans-2-acylaminocyclohexyloxyacetyldipeptides of the formulas Ia and Ib ##STR3## wherein R.sub.1 is --CO--R.sub.6, R.sub.6 is C.sub.1 -C.sub.18 alkyl,R.sub.2 is --H,R.sub.3 is --H or C.sub.1 -C.sub.12 alkyl,R.sub.4 is --OR.sub.8 or --NHR.sub.9,R.sub.8 is --H, C.sub.1 -C.sub.8 alkyl or benzyl,R.sub.9 is --H, C.sub.1 -C.sub.18 alkyl or benzyl,R.sub.5 is --OR.Type: GrantFiled: August 19, 1991Date of Patent: July 27, 1993Assignee: Univerza Edvarda Kardelja v LjubljanaInventors: Slavko Pecar, Danijel Kikelj, Uros Urleb, Marija Sollner, Gasper Marc, Ales Krbavcic, Vlado Kotnik, Branka Wraber-Herzog, Sasa Simcie, Alojz Than, Lidija Klamfer, Lucka Povsic, Zdravko Kopitar, Anton Stalc
-
Patent number: 5231183Abstract: A process for producing an enyne derivative, and intermediate, which is useful for preparing compounds showing strong inhibiting activities against squalane.epoxidase of Eumycetes and strong anti-cholesterol activities. The process comprises reacting a compound of the formula:Z--CH.sub.2 --CH.dbd.CH--W [I]wherein W is a halogen atom, and Z is a leaving group, with an amine in the presence of a base, if necessary, to obtain a compound of the formula: ##STR1## then reacting an acetylene derivative to this compound in the presence of a palladium catalyst, to obtain a compound of the formula: ##STR2## and, if necessary, N-alkylating this compound.Type: GrantFiled: March 27, 1992Date of Patent: July 27, 1993Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Susumu Nakagawa, Akira Asai, Satoru Kuroyanagi, Makoto Ishihara, Yoshiharu Tanaka
-
Patent number: 5210288Abstract: The invention relates to a process for the preparation of D-(-)-4-hydroxyphenylglycine and L-(+)-4-hydroxyphenylglycine starting from D.L.-4-hydroxyphenylglycine. According to the invention the D.L.-4-hydroxyphenylglycine is dissolved in a suitable solvent or a mixture of solvents at an increased temperature, which solvent mixture comprises an organic solvent, H.sub.2 SO.sub.4 and water. Then the solution obtained is cooled and to the cooled solution are added D-(-)-4-hydroxyphenylglycine sulphate inoculation crystals for crystallizing the D-(-)-4-hydroxyphenylglycine sulphate, followed by filtering of the formed crystals. For recovery of L-(+)-4-hydroxyphenylglycine sulphate remaining in the mother liquor, the mother liquor is heated, followed by addition of D.L.-4-hydroxyphenylglycine and a solution of H.sub.2 SO.sub.4 and water.Type: GrantFiled: March 14, 1991Date of Patent: May 11, 1993Inventor: Gerard Kessels
-
Patent number: 5198583Abstract: The optically active antiviral compound [1R-(1.alpha., 2.beta., 3.alpha.)]-2-amino-9-[2,3-bis(hydroxymethyl)-cyclobutyl]-1,9-dihydro-6H-pu rin-6-one and novel intermediates useful in its preparation are described.Type: GrantFiled: October 3, 1991Date of Patent: March 30, 1993Assignee: E. R. Squibb & Sons, Inc.Inventors: Gregory S. Bisacchi, Toomas Mitt
-
Patent number: 5192358Abstract: Oxalylhydroxamic acid derivatives of the formula IR.sup.1 --ON(R.sup.2)--CO--CO--X--R.sup.3 I,where the substituents have the following meanings:X is oxygen or sulfur;R.sup.1 issubstituted or unsubstituted alkyl, alkenyl or alkynyl;substituted or unsubstituted monocyclic or polycyclic cycloalkyl or cycloalkylmethyl;substituted or unsubstituted phenyl or phenyl-C.sub.1 -C.sub.4 -alkyl;R.sup.2 is hydrogen or alkyl;R.sup.3 issubstituted or unsubstituted alkyl, alkenyl or alkynyl;substituted or unsubstituted monocyclic or polycyclic cycloalkyl;substituted or unsubstituted phenyl-C.sub.1 -C.sub.4 -alkyl or phenoxy-C.sub.1 -C.sub.4 -alkyl;and their agriculturally useful salts; their manufacture; growth-regulating agents containing them; and methods of regulating plant growth.Type: GrantFiled: July 1, 1991Date of Patent: March 9, 1993Assignee: BASF AktiengesellschaftInventors: Costin Rentzea, Wilhelm Rademacher
-
Patent number: 5180744Abstract: Non-peptidyl compounds characterized generally as aralkyl-N-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 is hydroxy; wherein R.sub.7 is isobutyl or ethyl; and wherein each of R.sub.8 and R.sub.9 is hydrido; or a pharmaceutically-acceptable salt thereof.Type: GrantFiled: July 29, 1991Date of Patent: January 19, 1993Assignee: G. D. Searle & Co.Inventors: Gunnar J. Hanson, John S. Baran, Dave Weissing, Mark Russell
-
Patent number: 5179097Abstract: Novel choline salts of non-steroidal anti-inflammatory carboxylic acids and anti-lipidemic carboxylic acids are described. Additionally, blends of choline salts with the above carboxylic acids are also described. The new salts and compositions offer new therapeutic advantages.Type: GrantFiled: June 10, 1991Date of Patent: January 12, 1993Inventor: Isaac A. Angres
-
Patent number: 5177109Abstract: Compounds, compositions and methods are described for treating a CNS disorder such as a cognitive disorder, epilepsy, depression, Parkinson's disease, Alzheimer's disease, a neurodegenerative disease or neurotoxic injury. Compound of interest are 2-amino-4,5-methyleneadipic acid compounds and derivatives defined by the formula I: ##STR1## wherein R.sup.1 is selected from hydrido, alkyl, cycloalkyl, aralkyl, aryloxyalkyl, arylthioalkyl, ##STR2## with each of R.sup.2, R.sup.3, R.sup.4 and R.sup.5 being independently selected from hydrido, alkyl, cycloalkyl, aryl and aralkyl; wherein each of X and Y is independently selected from hydroxyl, alkoxy, alkylthio, amino and ##STR3## with each of R.sup.6 and R.sup.7 being independently selected from hydrido, alkyl, cycloalkyl, aryl and aralkyl; wherein any of R.sup.1 through R.sup.Type: GrantFiled: July 19, 1991Date of Patent: January 5, 1993Assignee: G. D. Searle & Co.Inventors: Roberto Pellicciari, Benedetto Natalini, Maura Marinozzi, Alexis A. Cordi, Joseph B. Monahan, Thomas H. Lanthorn
-
Patent number: 5175338Abstract: An isocarbacyclin derivative represented by the following formula [VII'] ##STR1## wherein A represents, a hydrocarbylcarboxylate group, a carboxymethoxycarbonyl group, an amide group, an acyloxymethyl group or a hydroxymethyl group; R.sup.4 represents H, a methyl group or a vinyl group; R.sup.5 represents a (substituted)alkyl group, a phenyl group, a phenoxy group or a cycloalkyl group; R.sup.e22 and R.sup.e32 represent H or a hydroxyprotecting group; n is 0 or 1;and a pharmaceutically acceptable salt thereof.Type: GrantFiled: September 14, 1990Date of Patent: December 29, 1992Assignee: Teijin LimitedInventors: Atsuo Hazato, Toshio Tanaka, Noriaki Okamura, Kiyoshi Bannai, Seizi Kurozumi, Masaaki Suzuki, Ryoji Noyori
-
Patent number: 5169867Abstract: Compounds of formula ##STR1## wherein R.sub.1 is amino or is a radical ##STR2## wherein R.sub.3 is lower alkyl, hydroxy-lower alkyl, lower alkoxy-lower alkyl, carboxy, lower alkoxycarbonyl, phenyl, phenyl substituted by lower alkyl, halo-lower alkyl, hydroxy-lower alkyl, halogen, hydroxy, lower alkoxy, lower alkanoyloxy and/or by nitro, pyridyl, pyridyl substituted by lower alkyl, hydroxy-lower alkyl, lower alkoxy-lower alkyl, phosphonooxy-lower alkyl, lower alkanoyl, carboxy, lower alkoxycarbonyl, hydroxy, lower alkoxy, lower alkanoyloxy, nitro and/or by oxido, or quinolyl, R.sub.4 is hydrogen, lower alkyl, hydroxy-lower alkyl or halo-lower alkyl, or R.sub.3 and R.sub.4 together are C.sub.4 -C.sub.6 alkylene or benzo-C.sub.4 -C.sub.6 alkylene, and R.sub.2 is straight-chain C.sub.1 -C.sub.4 alkyl, and salts thereof, have a strong specific inhibitory action on the enzyme ornithine decarboxylase. The compounds of Formula I are prepared according to processes known per se.Type: GrantFiled: April 8, 1991Date of Patent: December 8, 1992Assignee: Ciba-Geigy CorporationInventors: Jaroslav Stanek, Jorg Frei
-
Patent number: 5169976Abstract: Variously substituted 4-(biphen-2-ylmethylcarbamoyl)-3-hydroxybutyric acids and esters, also named as N-(biphen-2-yl)-3-hydroxyglutaramic acid derivatives, are blood cholesterol lowering agents and so are useful in the prevention and treatment of cardiovascular diseases such as atherosclerosis.Type: GrantFiled: May 3, 1990Date of Patent: December 8, 1992Assignee: Pfizer Inc.Inventor: Peter A. McCarthy
-
Patent number: 5166400Abstract: Process and intermediates for isopropyl 3S-amino-4-cyclohexyl-2R-hydroxybutyrate and 3S-amino-2R-hydroxy-5-methylhexanoate from R-malic acid. These products are of known utility in the synthesis of certain renin inhibitors.Type: GrantFiled: July 18, 1991Date of Patent: November 24, 1992Assignee: Pfizer Inc.Inventor: Robert W. Dugger
-
Patent number: 5166218Abstract: Tertiary and secondary amines of the formulas ##STR1## and ##STR2## wherein n is the integer 1 or 2,R is hydrogen, lower-alkanoyl or phenyl-lower-alkanoyl,X.sup.1 is phenoxymethyl optionally mono-fluorinated or mono-chlorinated in the ortho-position,X.sup.2 is lower-alkyl, phenoxymethyl optionally mono-fluorinated or mono-chlorinated in the ortho-position or phenyl optionally monosubstituted by fluorine, chlorine, trifluoromethyl or lower-alkoxy,Y is hydrogen or methyl, andZ is a phenyl or thienyl residue substituted as hereinafter described,and the physiologically and pharmaceutically compatible salts are described. The compounds of formulas I and V-1 have catabolic activity and can be used for the treatment of obesity and diabetes mellitus or for the treatment of conditions which are associated with an increased protein breakdown, or as feed additives for fattening animals. The compounds of formulas I and V-1 can be prepared starting from corresponding primary amines.Type: GrantFiled: August 12, 1991Date of Patent: November 24, 1992Assignee: Hoffmann-La Roche Inc.Inventors: Leo Alig, Marcel Muller
-
Patent number: 5166402Abstract: Herbicidal .alpha.-(5-aryloxy-naphthalen-1-yl-oxy)propionic acid derivatives of the formula ##STR1## in which R.sup.1 stands for hydrogen, halogen, cyano or trifluoromethyl,R.sup.2 stands for hydrogen or halogen,R.sup.3 stands for halogen, cyano, trifluoromethyl or trifluoromethoxy,R.sup.4 stands for hydrogen or halogen,R.sup.5 stands for hydrogen or halogen andZ stands for halogen, hydroxyl, amino, alkylamino, alkenylamino, alkinylamino, arylamino, aralkylamino, alkoxycarbonylalkylamino, cyanamino, dialkylamino, dialkenylamino, alkylsulphonylamino, arylsulphonylamino, hydroxylamino, alkoxyamino, hydrazino, alkylsulphonylhydrazino, arylsulphonylhydrazino, alkylthio, arylthio, aralkylthio, alkoxycarbonylalkylthio or for the --O--R.sup.6 group,wherein R.sup.6 can be various organic radicals.The starting material naphthol of the formula ##STR2## is also new.Type: GrantFiled: November 1, 1990Date of Patent: November 24, 1992Assignee: Bayer AktiengesellschaftInventors: Michael Haug, Hans-Joachim Santel, Robert R. Schmidt, Harry Strang
-
Patent number: 5162311Abstract: The invention discloses certain substituted .alpha.-aminoacids having the formula ##STR1## where m and n are 1 or 2, and R, R.sub.1, R.sub.2, R.sub.3 and Y have various significances, which compounds are useful in treating epilepsy, disorders associated with excess GH or LH secretion, anxiety, schizophrenia, depression, CNS degenerative disorders, cerebral hypoxic conditions and stress-related psychiatric disorders.Type: GrantFiled: August 19, 1991Date of Patent: November 10, 1992Assignee: Sandoz Pharmaceuticals Corp.Inventors: Paul L. Herrling, Werner Muller
-
Patent number: 5162353Abstract: The invention relates to carbacyclin derivatives with general formula I: ##STR1## in which Y.sub.1 stands for the radical --CH.sub.2 --X--(CH.sub.2).sub.n --R.sub.1 or the radical ##STR2## n, 1 or 3, R.sub.1, the radical ##STR3## the radical ##STR4## R.sub.9 stands for the radical --(CH.sub.2).sub.m --R.sub.6 or the radical --(CH.sub.2).sub.m-o --[Z.sub.1 --(CH.sub.2).sub.m-p ].sub.x --[Z.sub.2 --(CH.sub.2).sub.m-q ].sub.y --R.sub.6,m=2-20,o, p, and q are less than or equal to 19,x, y=0, 1 or 2,Z.sub.1 stands for a cis--CH.dbd.CH group, a trans--CH.dbd.CH group of a --C.dbd.C group, and each of these groups must be separated at least by a methylene group from the C-9 carbon atom of the carbacyclin bicyclic compound,Z.sub.2 stands for oxygen, sulfur, an NH or an N methyl group,R.sub.6 stands for amino, methylamino, hydroxy, carboxy or mercapto,X an oxygen atom or a methylene group,Y.sub.2 hydrogen or fluorine,A a --CH.sub.2 --CH.sub.2, trans--CH.dbd.CH or --C.dbd.Type: GrantFiled: August 21, 1990Date of Patent: November 10, 1992Assignee: Schering AktiengesellschaftInventors: Helmut Vorbrueggen, Bob Nieuweboer, Claus-Steffen Stuerzebecher
-
Patent number: 5149859Abstract: A naphthalene derivative having the formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom, a C.sub.1 -C.sub.5 alkyl group or a non-toxic salt moiety; R.sup.2 and R.sup.3 independently represent a hydrogen atom or --OR.sup.4 where R.sup.4 represents a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group;A represents a group: ##STR2## [where X.sup.1 and X.sup.2 represents an oxygen atom or N--OR.sup.5 (where R.sup.5 represents a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group)], a group: ##STR3## [where Y.sup.1 and Y.sup.2 independently an oxygen atom or a group N--OR.sup.6 (where R.sup.6 represents a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group)], or a group: ##STR4## (where n is 0 or 1); and B represents --(CH.sub.2).sub.m --wherein m is an integer of 1, to 8,--(CH.sub.2).sub.m.sbsb.1 --O--(CH.sub.2).sub.m.sbsb.2 --wherein m.sub.1 and m.sub.2 are independently 1 or 2, or ##STR5## wherein m.sub.3 is 0 or 1.Type: GrantFiled: September 14, 1990Date of Patent: September 22, 1992Assignee: Teijin LimitedInventors: Atsuo Hazato, Takumi Takeyasu, Koji Tomimori, Yoshinori Kato
-
Patent number: 5145874Abstract: Provided are cyclic hydrocarbons of Formula I ##STR1## with an aminoalkyl sidechain that are useful for treating phospholipase A2 mediated conditions, diabetes, and obesity.Type: GrantFiled: February 25, 1991Date of Patent: September 8, 1992Assignee: The Upjohn CompanyInventors: Roy A. Johnson, Gordon L. Bundy, Gilbert A. Youngdale, Douglas R. Morton, Donald P. Wallach, deceased, by Vera M. Wallach, legal representative
-
Patent number: 5138091Abstract: Cardioactive dihydropyridines of the formula ##STR1## in which Y is ##STR2## A is H or CH.sub.3, B is --NH, --NH--CO--, --NH--CS--, --NH--COO--, --NH--SO.sub.2 --or --NH--CO--NH-- or --NH--CS--NH--, andR.sup.13 and R.sup.14 each independently is H or an organic radical,and salts thereof. The Y can be hydrolyzed off. The other radicals on the dihydropyridine moiety can also be varied.Type: GrantFiled: November 9, 1990Date of Patent: August 11, 1992Assignee: Bayer AktiengesellschaftInventors: Jurgen Stoltefuss, Martin Bechem, Rainer Gross, Siegbert Hebisch, Matthias Schramm
-
Patent number: 5138071Abstract: A process for preparing dipeptides with N-terminal non-proteinogenous amino acids of the formula ##STR1## in which R.sup.1 to R.sup.6 have the meaning stated in the description, from compounds of the formula ##STR2## is described.Type: GrantFiled: March 18, 1991Date of Patent: August 11, 1992Assignee: BASF AktiengesellschaftInventors: Ulrich Schoellkopf, Ulrich Groth, Meinolf Lange
-
Patent number: 5135737Abstract: Disclosed are amplifier molecules: various organic compounds having branched structures terminating with amine groups to which pharmacologically active groups can be chemically attached. A number of MRI contrast-enhancing agents were synthesized, each comprising plural active groups, such as stable nitroxides and complexes of trivalent metal cations. Such syntheses were successfully performed using a number of amplifiers having different branched structures, demonstrating the general utility of the pertinent chemistry in the synthesis of amplifiers having any of a wide variety of pharmacologically active groups. Amplifiers were also synthesized having linkers terminating with chemically reactive groups such as isothiocyanates, which render the amplifier bifunctional: attachable to polymers, biomacromolecules, or other biocompatible entity possessing multiple reactive sites such as terminal amines.Type: GrantFiled: September 5, 1989Date of Patent: August 4, 1992Assignee: The State of Oregon Acting by and through the State Board of Higher Education on behalf of the University of OregonInventor: John F. W. Keana