The Hetero Ring Is Five-membered Patents (Class 549/6)
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Patent number: 5670493Abstract: A compound of formula (I): ##STR1## in which: R.sub.1, R.sub.2, which may be identical or different, represent hydrogen or halogen, or alkyl, alkoxy, nitro or trihalomethyl,X represents CO, SO.sub.2 or CH.sub.2,A.sub.1 represents any one of the groups as defined in the description,A.sub.2 represents --(CH.sub.2).sub.n or --CH.dbd.CH--,R.sub.3, R.sub.4, which may be identical or different, represent hydrogen or alkyl,its isomers as well as its addition salts with a pharmaceutically acceptable base and medicinal product containing the same are useful as angiogenesis inhibitors.Type: GrantFiled: July 19, 1996Date of Patent: September 23, 1997Assignee: Adir et CompagnieInventors: Alex Cordi, Patrice Desos, Angela D. Morris, Ghanem Atassi
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Patent number: 5658897Abstract: The present invention relates to cyclopentane (or cyclopentane) heptanoic or cyclopentane (or cyclopentene) heptenoic acid, 2-hydrocarbyl phosphinyloxyalkyl or phosphonamidoalkyl, 1-esters, and derivatives thereof, useful as therapeutic agents. In particular, the therapeutic agents of this invention are useful as ocular hypotensives.Type: GrantFiled: April 8, 1996Date of Patent: August 19, 1997Assignee: AllerganInventor: Robert M. Burk
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Patent number: 5618941Abstract: Compounds of formula (I) wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each H or C.sub.1 -C.sub.4 alkyl; R.sup.5 is (CH.sub.2).sub.m NHSO.sub.2 R.sup.6 or (CH).sub.m NHCOR.sup.6 ; R.sup.6 is C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl optionally substituted by aryl, aryl or heteroaryl; R.sup.7 is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo, CF.sub.3, OCF.sub.3, CN, CONH.sub.2, or S(O).sub.n (C.sub.1 -C.sub.4 alkyl); X is CH.sub.2, CHCH.sub.3, CH(OH), C(OH)CH.sub.3, C.dbd.CH.sub.2, CO or O; m is 0 or 1 and n is 0, 1 or 2, and their pharmaceutically acceptable salts and biolabile esters, are antagonists of thromboxane A.sub.2 of utility, particulary in combination with a thromboxane synthetase inhibitor, in the treatment of atherosclerosis and unstable angina and for prevention of reocclusion after percutaneous transluminal angioplasty.Type: GrantFiled: March 15, 1995Date of Patent: April 8, 1997Assignee: Pfizer Inc.Inventors: Roger P. Dickinson, Kevin N. Dack, John Steele
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Patent number: 5602115Abstract: The bisphosphonates of formula (III)R.sub.2 --X--(CW).sub.m1 --CR.sub.3 R.sub.4 --CH.sub.2 --CM[PO--(OR.sub.1).sub.2 ].sub.2 (III)bicyclic bisphosphonates (V), and cyclic bisphosphonates (VII) are useful as antiarthritic agents and do not have the side effects of anti-arthritic agents which are prostaglandin synthetase inhibitors.Type: GrantFiled: November 28, 1994Date of Patent: February 11, 1997Assignee: The Upjohn CompanyInventor: Richard A. Nugent
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Patent number: 5591891Abstract: N-[Mercaptoacyl(amino acid or peptide)] compounds and S-lipophilic aliphatic carbonyl derivatives thereof, and pharmaceutical compositions comprising such compounds, as well as the use of these compounds as antihypertensives by the inhibition of neutral endopeptidase and/or peptidyldipeptidase A are disclosed. Methods for preparing the such compounds and derivatives are disclosed also.Type: GrantFiled: January 24, 1994Date of Patent: January 7, 1997Assignee: Institut National de la Sante et de la Recherche Medicale (INSERM)Inventors: Marie-Claude Fournie-Zaluski, Bernard-Pierre Roques
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Patent number: 5552535Abstract: A method for the synthesis of a plurality of oligonucleotides comprising the steps of(i) forming a first oligonucleotide on a first cleavable link attached to a solid support;(ii) attaching to the first oligonucleotide a cleavable linker moiety;(iii) forming a second oligonucleotide on the cleavable linker moiety; and(iv) cleaving the first cleavable link and the cleavable linker moiety to give a plurality of oligonucleotides; wherein the cleavable linker moiety is of the Formula (1): ##STR1## in which A.sup.1, A.sup.2 and E are as defined herein, and novel compounds which may be used in the operation of the method.Type: GrantFiled: November 7, 1994Date of Patent: September 3, 1996Assignee: Zeneca LimitedInventors: Michael J. McLean, David Holland, Andrew J. Garman, Robert C. Sheppard
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Patent number: 5525736Abstract: A process for the production of a 5-7 membered ring cyclic sulfonium salt compound, including a 5-7 membered ring cyclic sulfonium salt compound having a non-nucleophilic anion, is described. Members of the latter group are potentially useful as initiators for cationic polymerizations. The process comprises reacting a 1.4-, 1.5-, or 1.6-diol compound or a 5-7 membered ring cyclic ether compound with a mercapto compound and a strong protonic acid yielding the cyclic sulfonium salt compound. Some compounds described are also novel compounds per se.Type: GrantFiled: February 23, 1995Date of Patent: June 11, 1996Assignee: Ciba-Geigy CorporationInventors: Jan-Erik Nystrom, Per Engelhardt, Katarina Beierlein, Mikael Sellen, Bjorn Elman, Jan Vagberg, Martin Nylof
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Patent number: 5523296Abstract: Compounds of the formula ##STR1## where W is (CH.sub.2).sub.n where n is 1 or 2, or n is 0 and W represents lower alkyl groups attached to each oxygen;m is an integer between 1 and 8;R.sub.1 is COOH or a pharmaceutically acceptable salt thereof, COOR.sub.4, CONR.sub.5 R.sub.6, CONR.sub.5 SO.sub.2 R.sub.7, CH.sub.2 OH, CH.sub.2 OR.sub.7, CH.sub.2 O--COR.sub.7, CH.sub.2 O--CONR.sub.5, R.sub.7, CH.sub.2 OCOOR.sub.7, CH.sub.2 NH.sub.2, CH.sub.2 NR.sub.5 R.sub.6, CH.sub.2 NR.sub.5 COR.sub.7, CHO, CH(OR.sub.8).sub.2, CHOR.sub.9 O, --COR.sub.10, CR.sub.10 (OR.sub.8).sub.2, or CR.sub.10 OR.sub.9 O, where R.sub.4 is an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R.sub.4 is phenyl or lower alkylphenyl, R.sub.5 and R.sub.6 independently are hydrogen, an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or phenyl or lower alkylphenyl, R.sub.7 is alkyl of 1 to 10 carbons, phenyl or lower alkylphenyl, R.sub.8 is lower alkyl, and R.sub.Type: GrantFiled: November 28, 1994Date of Patent: June 4, 1996Assignee: Allergan, Inc.Inventors: Robert M. Burk, David F. Woodward
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Patent number: 5508438Abstract: Novel, racemic and optically active phosphorus compounds of the formula ##STR1## wherein R signifies lower alkyl, lower alkoxy, hydroxy or a protected hydroxy group, R.sup.1 and R.sup.2 are different from each other and represent lower alkyl, cycloalkyl, aryl, a five-membered heteroaromatic or a group of the formula ##STR2## are described. The compounds of formula I are useful in the form of complexes with a metal of Group VIII as catalysts for asymmetric hydrogenations and for enantioselective hydrogen displacements in prochiral allylic systems.Type: GrantFiled: September 24, 1993Date of Patent: April 16, 1996Assignee: Hoffmann-La Roche Inc.Inventors: Emil A. Broger, Marco Cereghetti
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Patent number: 5480645Abstract: Hydroxyamines N-acyl derivatives with benzochroman or 2,3-dihydrobenzofuran carboxy acids and relative pharmaceutical composition for the therapeutic treatment of those CNS, vascular, cardiovascular, dermatologic and ophthalmic pathologies wherein it is important to associate an inflammatory modulation effect to an antioxidant activity.Type: GrantFiled: December 29, 1993Date of Patent: January 2, 1996Assignee: LifeGroup S.p.A.Inventors: Francesco Della Valle, Silvana Lorenzi, Gabriele Marcolongo
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Patent number: 5472956Abstract: Cyclophosphamide analogs are provided of the general formula: ##STR1## wherein R.sup.1 and R.sup.2 are each (C.sub.2 -C.sub.6)alkyl, substituted with a leaving group such as halo or alkylsulfonyl, R.sup.3 and R.sup.4 are the same as R.sup.1 and R.sup.2 or are H and Ar is a heteroaromatic ring and the pharmaceutically acceptable salts thereof.Type: GrantFiled: January 21, 1994Date of Patent: December 5, 1995Assignee: Research Corporation Technologies, Inc.Inventors: Richard F. Borch, James P. Schmidt
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Patent number: 5436245Abstract: Hypotensive activity is exhibited by new phosphonate substituted amino or imino acids of the formula ##STR1## isomeric mixtures thereof and pharmaceutically acceptable salts thereof, wherein:X is an imino or amino acid of the formula ##STR2##Type: GrantFiled: November 17, 1993Date of Patent: July 25, 1995Assignee: E. R. Squibb & Sons, Inc.Inventor: Donald S. Karanewsky
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Patent number: 5428058Abstract: There are disclosed compounds of the formula: ##STR1## wherein R.sup.1 is hydrogen, alkyl, cycloalkyl, arylalkyl, --(CH.sub.2).sub.r CH.dbd.CH.sub.2, --(CH.sub.2).sub.s OY, --(CH.sub.2).sub.t CH(OZ)CH.sub.3, or Ar;X is O, S, or NR.sup.2 ;Y and Z are each, independently, hydrogen, alkyl, or --COR.sup.3 ;R.sup.2 and R.sup.3 are each, independently, hydrogen, alkyl, or arylalkyl;Ar is an aryl radical that may be optionally substituted;m=1-5;n=0-1;p=1-9;r=0-6;s=2-6; andt=0-6or a pharmaceutically acceptable salt thereof which are useful as antiinflammatory agents.Type: GrantFiled: September 28, 1994Date of Patent: June 27, 1995Assignee: American Home Products CorporationInventor: Dominic R. Mobilio
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Patent number: 5412141Abstract: The bisphosphonates of formula (III)R.sub.2 --X--(CW).sub.m1 --CR.sub.3 R.sub.4 --CH.sub.2 --CM[PO--(OR.sub.1).sub.2 ].sub.2 (III)bicyclic bisphosphonates (V), and cyclic bisphosphonates (VII) are useful as anti-arthritic agents and do not have the side effects of anti-arthritic agents which are prostaglandin synthetase inhibitors.Type: GrantFiled: February 19, 1993Date of Patent: May 2, 1995Assignee: The Upjohn CompanyInventor: Richard A. Nugent
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Patent number: 5410060Abstract: Arenebisphosphine oxides of the general formula ##STR1## where R.sup.1 to R.sup.4 independently of one another are each hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.5 -C.sub.10 -aryl, C.sub.5 -C.sub.12 -aryloxy or C.sub.7-C.sub.14 -arylalkoxy, R.sup.5 and R.sup.6 independently of one another may each be C.sub.1 -C.sub.6 -alkyl, C.sub.5 -C.sub.10 -cycloalkyl or C.sub.5 -C.sub.12 -aryl, each of which may furthermore contain one or two nitrogen or sulfur atoms in the ring system or carry one or two halogen atoms or C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -alkoxy groups as substituent on the ring system, or C.sub.1 -C.sub.6 -alkoxy, C.sub.3 -C.sub.8 -alkoxyalkoxy, C.sub.5 -C.sub.12 -aryloxy or C.sub.7 -C.sub.14 -arylalkoxy, or R.sup.5 and R.sup.6 together form a bridge of 2 to 10 carbon atoms, in which some of the carbon atoms may furthermore be part of an aromatic ring.Type: GrantFiled: December 2, 1993Date of Patent: April 25, 1995Assignee: BASF AktiengesellschaftInventors: Jochen Schroeder, Wolfgang Siegel, Matthias Lokai
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Patent number: 5407922Abstract: Compounds having GABA.sub.B -antagonistic properties, for example those of formula I ##STR1## wherein one of the radicals R.sub.1, R.sub.2 and R.sub.3 is hydrogen or an aliphatic, cycloaliphatic, araliphatic or aromatic radical, another is hydrogen or, in the case of R.sub.1 or R.sub.2, hydroxy or, in the case of R.sub.1, halogen or, in the case of R.sub.2 together with R.sub.2 ', oxo, and the remaining radical is hydrogen, R.sub.1 ' is hydrogen or halogen, R.sub.2 ' is hydrogen, hydroxy or, together with R.sub.2, is oxo, R.sub.4 and R.sub.5 are hydrogen or R.sub.4 is an araliphatic or heteroarylaliphatic radical and R.sub.5 is hydrogen or an aliphatic radical, and R is an aliphatic, cycloaliphatic, cycloaliphatic-aliphatic, araliphatic, heteroarylaliphatic or aromatic radical having at least 2 carbon atoms or, when R.sub.1 is hydrogen or hydroxy, R.sub.2 is an aromatic radical and R.sub.1 ', R.sub.2 ' and R.sub.Type: GrantFiled: May 3, 1993Date of Patent: April 18, 1995Assignee: Ciba-Geigy CorporationInventors: Christian Marescaux, Raymond Bernasconi, Markus Schmutz, Wolfgang Frostl, Stuart J. Mickel
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Patent number: 5405841Abstract: The invention relates to new phosphorylated aza compounds, to processes for their preparation and to their use as pesticides, in particular as soil-acting insecticides and nematicide.The new compounds have the general formula (I) ##STR1## in which R.sup.1 -R.sup.5, X and Y are defined as in the specification, with the exception of compound O-ethyl S-propyl 3-(6-chloro-3-pyridinylmethyl)-2-nitroimino-imidazolidine-1-thiophosphate.Type: GrantFiled: November 30, 1993Date of Patent: April 11, 1995Assignee: Bayer AktiengesellschaftInventors: Fritz Maurer, Jurgen Hartwig, Christoph Erdelen
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Patent number: 5403932Abstract: Compounds of the formula: ##STR1## which is further defined herein, possess anti-tumor activity.Type: GrantFiled: June 15, 1994Date of Patent: April 4, 1995Assignee: Research Corporation Technologies, Inc.Inventors: Richard F. Borch, Gregory W. Canute, Ronald R. Valente
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Patent number: 5374628Abstract: Phosphonic acid squalene synthetase inhibitors are provided which are effective in lowering serum cholesterol and have the formula ##STR1## wherein m is 0 to 3, n is 1 to 5, Y.sup.1 and Y.sup.2 are H or halogen, R.sup.2, R.sup.3 and R.sup.4 are H, metal ion, C.sub.1 to C.sub.8 alkyl, C.sub.3 to C.sub.12 alkenyl, or prodrug ester, and R.sup.1 is a substituted or unsubstituted heteroaryl group or a substituted phenyl group.Type: GrantFiled: October 18, 1993Date of Patent: December 20, 1994Assignee: E. R. Squibb & Sons, Inc.Inventor: Scott A. Biller
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Patent number: 5368985Abstract: Bisacylphosphine sulfides of formula I ##STR1## wherein R.sub.1 is unsubstituted C.sub.1 -C.sub.18 or C.sub.1 -C.sub.8 alkyl which is substituted by phenyl, --CN, C.sub.1 -C.sub.12 alkoxy or halogen, C.sub.2 -C.sub.18 alkenyl, unsubstituted C.sub.5 -C.sub.8 cycloalkyl or C.sub.5 -C.sub.8 cycloalkyl which is substituted by C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy or halogen, unsubstituted C.sub.6 -C.sub.12 aryl or C.sub.6 -C.sub.12 aryl which is substituted by halogen, C.sub.1 -C.sub.12 alkyl or C.sub.1 -C.sub.12 alkoxy, or a 5- or 6-membered aromatic heterocyclic radical which contains oxygen, sulfur and/or nitrogen and is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, andR.sub.2 and R.sub.3 are each independently of the other unsubstituted C.sub.1 -C.sub.18 alkyl or C.sub.1 -C.sub.8 alkyl which is substituted by phenyl, halogen or C.sub.1 -C.sub.12 alkoxy, C.sub.2 -C.sub.6 alkenyl, unsubstituted C.sub.5 -C.sub.8 cycloalkyl or C.sub.5 -C.sub.Type: GrantFiled: February 28, 1994Date of Patent: November 29, 1994Assignee: Ciba-Geigy CorporationInventors: Werner Rutsch, Gebhard Hug, Manfred Kohler
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Patent number: 5334766Abstract: A process for the resolution of racemic diphosphine oxides into the optically active antipodes by reacting the racemate with a resolving agent comprising using a carbamate or thiocarbamate of an optically active .alpha.-hydroxycarboxylic acid or .alpha.-aminocarboxylic acid as the resolving agent.Type: GrantFiled: April 9, 1992Date of Patent: August 2, 1994Assignee: Hoffmann-La Roche Inc.Inventors: Marco Cereghetti, Alain Rageot
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Patent number: 5312954Abstract: Novel bisphosphonates comprise compounds of the formula (I) ##STR1## wherein m and l are independently 1 or 2; R.sub.1 represents hydrogen, a lower alkyl group, or an alkali metal cation; R.sub.2 represents hydrogen, a lower alkyl group or an alkali metal cation; Y represents .dbd.0 or .dbd.N--OH, or --OH and X represents --(CH.sub.2).sub.n --, a branched alkylene group, or a branched or straight alkenylene or alkynylene chain optionally substituted by one or more oxygen or nitrogen atoms, wherein n is an integer from 3 to 24. Further definitions of X are included in the description.Type: GrantFiled: May 13, 1992Date of Patent: May 17, 1994Assignee: Yissum, Research Development Company of the Hebrew University of JerusalemInventors: Eli Breuer, Gershon Golomb
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Patent number: 5306727Abstract: Cyclophosphamide analogs are provided of the general formula: ##STR1## wherein R.sup.1 and R.sup.2 are each (C.sub.2 -C.sub.6)alkyl, substituted with a leaving group such as halo or alkylsulfonyl, R.sup.3 and R.sup.4 are the same as R.sup.1 and R.sup.2 or are H and Ar is a heteroaromatic ring and the pharmaceutically acceptable salts thereof.Type: GrantFiled: April 30, 1993Date of Patent: April 26, 1994Assignee: Research Corporation Technologies, Inc.Inventors: Richard F. Borch, James P. Schmidt
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Patent number: 5274155Abstract: A process for the preparation of compounds of formula ##STR1## and pharmaceutically acceptable salts thereof; wherein X is --CH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --C.tbd.C-- or --CH.sub.2 O-- (where O is linked to Z); Z is a hydrophobic anchor R.sub.1 is hydrogen, alkyl, cycloalkyl or aryl; comprising the steps of:(A) reacting a compound of formula ##STR2## with a compound of formula ##STR3## or a compound of formula ##STR4## in the presence of an amine base or an alkali metal hydride in an organic solvent to form a compound having the formula ##STR5## (B) heating the compound of formula IX at a temperature of from about 100.degree. C. to about 200.degree. C., to form a compound of formula ##STR6## and (C) quenching the compounds of formula VIII with an acid provides the compounds of formula I.Type: GrantFiled: December 7, 1992Date of Patent: December 28, 1993Assignee: E. R. Squibb & Sons, Inc.Inventors: John K. Thottathil, David Kronenthal
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Patent number: 5274125Abstract: Novel, racemic and optically active phosphorus compounds of the formula ##STR1## wherein R signifies lower alkyl, lower alkoxy or a protected hydroxy group, R.sup.1 signifies a five membered heteroaromatic ring, R.sup.2 stands for lower alkyl or lower alkoxy and n represents the number 0, 1 or 2, are described. The compounds of formula I serve in the form of complexes with a metal of Group VIII as catalyst for asymmetric hydrogenations and for enantioselective hydrogen displacements in prochiral allylic systems.Type: GrantFiled: November 13, 1992Date of Patent: December 28, 1993Assignee: Hoffmann-La Roche Inc.Inventors: Emil A. Broger, Joseph Foricher, Bernd Heiser, Rudolf Schmid
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Patent number: 5274122Abstract: Homocysteine thiolactone derivatives in which the nitrogen is acylated with groups containing acidic functionalities have been synthesized. These include the succinyl, the carboxymethylglutaryl, the 3-phosphonopropionyl and the 3-sulfopropionyl derivatives. These thiolactones can be used to introduce a thiol functionality into proteins such as the outer membrane protein complex of Neisseria meninioitidis (OMPC) allowing conjugation with electrophilic ligands. This chemistry is similar to known N-acetyl-homocysteine thiolactone chemistry, but the pK.sub.a values are such that at pH 7, concomitant negative charge is introduced into the conjugate. Such negative charge neutralizes excess positive charge introduced when arginine- and lysine-rich peptides are bonded as ligands. In the case of OMPC, introduction of positive charge commonly effects irreversible precipitation of the conjugate. Conjugates prepared with the anionic thiolactones have improved solubility.Type: GrantFiled: October 15, 1992Date of Patent: December 28, 1993Assignee: Merck & Co., Inc.Inventors: Richard L. Tolman, Stephen Marburg, William J. Leanza
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Patent number: 5268388Abstract: Certain substituted semicarbazones, including all geometric and stereoisomers thereof, agricultural compositions containing them and their use as arthropodicides.Type: GrantFiled: November 2, 1992Date of Patent: December 7, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventors: John P. Daub, George P. Lahm, Bradford S. Marlin
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Patent number: 5250522Abstract: The present invention relates to the N-phosphonomethyl-biaryl substituted amino acid derivatives of formula I ##STR1## wherein X represents a direct bond, C.sub.1-4 -alkylene or C.sub.2 -C.sub.4 -alkenylene; R and R' represent independently hydrogen, carbocyclic aryl, 6-tetrahydronaphthyl, 5-indanyl, .alpha.-(trichloromethyl, carboxyl, esterified carboxyl or amidated carboxyl)substituted-(lower alkyl or aryl-lower alkyl), acyloxymethyl optionally monosubstituted on methyl carbon by C.sub.1-20 -alkyl, by C.sub.5 -C.sub.7 -cycloalkyl, by aryl or by aryl-lower alkyl; R.sub.1 represents monocyclic carbocyclic or monocyclic heterocyclic aryl; COR.sub.3 represents carboxyl or carboxyl derivatized in form of a pharmaceutically acceptable ester; R.sub.2 and R.sub.Type: GrantFiled: October 9, 1992Date of Patent: October 5, 1993Assignee: Ciba-Geigy CorporationInventor: Stephane De Lombaert
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Patent number: 5229375Abstract: Phosphine oxide-terminated allene-ene-yne compounds are disclosed that possess DNA-cleaving, antimicobial and tumor growth-inhibiting properties. Methods of making and using those compounds are also disclosed.Type: GrantFiled: August 1, 1990Date of Patent: July 20, 1993Assignee: Scripps Clinic and Research FoundationInventors: Peter E. Maligres, Kyriacos C. Nicolaou
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Patent number: 5210110Abstract: Silylated acylphosphine oxides of formula I ##STR1## in which R.sub.1, R.sub.2 and R.sub.3 are defined in the specification, are highly suitable as photoinitiators for the photopolymerization of compounds which can be polymerized by means of free radicals, namely ethylenically unsaturated compounds.Type: GrantFiled: November 18, 1991Date of Patent: May 11, 1993Assignee: Ciba-Geigy CorporationInventors: Werner Rutsch, Rinaldo Husler
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Patent number: 5204334Abstract: Benzoheterocyclylalkylaminoalkanediphosphonic acids of formula I ##STR1## wherein R.sub.1 and R.sub.2, independently of one another, are hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl, R.sub.3 is hydrogen or lower alkyl, X and Y, independently of one another, are oxy or thio, alk.sub.1 and alk.sub.2 are identical or different lower alkylene radicals, n is 0 or 1 and m and m', independently of one another, are 0, 1 or 2, the sum of n, m and m' being 1, 2 or 3, and their salts exhibit a pronounced regulatory action on the calcium metabolism of warm-blooded animals. They are prepared, for example, as follows: in a compound of the formula ##STR2## wherein R.sub.1, R.sub.2, n, m, m', X, Y, alk.sub.1 and alk.sub.2 are as defined above, R'.sub.3 is one of the groups R.sub.3 mentioned above or is an amino-protecting group R.sub.0, Z.sub.1 is a functionally modified phosphono group, and Z.sub.2 is a free or functionally modified phosphono group, converting functionally modified phosphono Z.sub.Type: GrantFiled: September 25, 1991Date of Patent: April 20, 1993Assignee: Ciba-Geigy CorporationInventors: Wolfgang Frostl, Knut A. Jaeggi
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Patent number: 5190929Abstract: Cyclophosphamides possessing anti-tumor activity and having the formula ##STR1## and salts thereof; wherein R is lower alkyl, aryl, aryl-lower alkyl or a nitrogen, sulfur or oxygen containing heterocyclic or heterocyclic lower alkyl, andR' is hydrogen, hydroxy or OOH with the proviso that when R' is hydrogen, R is other than methyl or phenyl and when R' is hydroxy, R is other than methyl.Type: GrantFiled: May 25, 1988Date of Patent: March 2, 1993Assignee: Research Corporation Technologies, Inc.Inventors: Richard F. Borch, Gregory W. Canute
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Patent number: 5190930Abstract: Araliphatylaminoalkanediphosphonic acids of formula ##STR1## wherein R.sub.1 is an aromatically substituted aliphatic radical, R.sub.2 is hydrogen or a monovalent aliphatic radical and alk is a divalent aliphatic radical, and their salts, exhibit a pronounced regulatory action on the calcium metabolism and can be used as medicaments for the treatment of diseases that are attributable to calcium metabolsim disorders. They are prepared, for example, by reacting a compound of formula ##STR2## wherein X.sub.3 is carboxy and R.sub.0 is a radical R.sub.2, with phosphorous acid and phosphorus trichloride and hydrolysing the primary product.Type: GrantFiled: December 20, 1991Date of Patent: March 2, 1993Assignee: Ciba-Geigy CorporationInventor: Knut A. Jaeggi
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Patent number: 5155100Abstract: The invention relates to the N-phosphonomethyl-biaryl substituted dipeptide derivatives of formula I ##STR1## wherein A represents a direct bond, lower alkylene, phenylene or cyclohexylene; m represents 1 or zero, provided that m represents 1 when A is a direct bond; R.sub.2 represents hydrogen, hydroxy, lower alkyl, aryl-lower alkyl, C.sub.5 -C.sub.Type: GrantFiled: May 1, 1991Date of Patent: October 13, 1992Assignee: Ciba-Geigy CorporationInventors: Mark D. Erion, Stephane De Lombaert
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Patent number: 5145990Abstract: Compounds of the formula: ##STR1## wherein R.sub.1 is C.sub.2- C.sub.12 linear or branched unsubstituted alkyl; C.sub.1- C.sub.12 linear or branched substituted alkyl; C.sub.2 -C.sub.12 linear or branched monoalkenyl; C.sub.2 -C.sub.12 linear or branched alkynyl; C.sub.7 -C.sub.20 aralkyl, wherein the alkyl chain is linear or branched C.sub.1- C.sub.8 and the aryl moiety is C.sub.6- C.sub.12 ; C.sub.4- C.sub.10 cycloalkylalkyl; C.sub.3- C.sub.7 cycloalkyl; wherein these values for R.sub.1, other than C.sub.2- C.sub.12 linear or branched unsubstituted alkyl, can be substituted by one or more of C.sub.1 -C.sub.4 alkoxy, C.sub.3- C.sub.6 cycloalkyloxy, C.sub.3- C.sub.6 cycloalkylthio, C.sub.6- C.sub.12 aryloxy, C.sub.1- C.sub.4 alkylthio, C.sub.6- C.sub.12 arylthio, C.sub.7- C.sub.10 aralkyloxy, C.sub.7- C.sub.16 aralkyl-thio; and R.sub.5 is H or C.sub.1- C.sub.12 linear or branched alkyl; C.sub.2- C.sub.12 linear or branched monoalkenyl; C.sub.7- C.sub.Type: GrantFiled: January 9, 1991Date of Patent: September 8, 1992Assignee: Merck & Co., Inc.Inventors: William H. Parsons, William R. Schoen, Arthur A. Patchett
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Patent number: 5110807Abstract: Araliphatylaminoalkanediphosphonic acids of formula ##STR1## wherein R.sub.1 is an aromatically substituted aliphatic radical, R.sub.2 is hydrogen or a monovalent aliphatic radical and alk is a divalent aliphatic radical, and their salts, exhibit a pronounced regulatory action on the calcium metabolism and can be used as medicaments for the treatment of diseases that are attributable to calcium metabolism disorders. They are prepared, for example, by reacting a compound of formula ##STR2## wherein X.sub.3 is a carboxy and R.sub.0 is a radical R.sub.2, with phosphorous acid and phosphorous trichloride and hydrolysing the primary product.Type: GrantFiled: March 28, 1990Date of Patent: May 5, 1992Assignee: Ciba-Geigy CorporationInventor: Knut A. Jaeggi
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Patent number: 5101053Abstract: Radiation sensitive sulfonium salts which contain (1) a sulfonium initiator portion, (2) a spacer portion, and (3) a reactive group portion. The spacer portion has the formula "-o-w- x-z-" wherein "w" is a single bond or one of --C(O)--, --C(O)O--, --C(O)S--, --C(O)NH-- --C(O)N(alkyl)--, --C(S)--, --C(S)S--,--S(O)--, --S(O)(O)--, or --S(O)(O)O--; "X" is an unsubstituted or substituted alkylene radical; and "Z" is --O--, --NH--, --N(C,--C.sub.6 -alkyl)--, or --N(phenyl)--. The reactive group portion is --CH.dbd.CH.sub.2 or --C(O)--C(Y).dbd.CH.sub.2 wherein "Y" is H, C.sub.1 -.sub.6 -alkyl, or phenyl. The sulfonium salts find use in curing monomers which can be subjected to cationic polymerization.Type: GrantFiled: January 9, 1990Date of Patent: March 31, 1992Assignee: BASF AktiengesellschaftInventor: Andreas Boettcher
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Patent number: 5099052Abstract: Silicon and aluminum complexes having the following formula: ##STR1## wherein x is 0 or 1, T is H or ##STR2## each R is independently selected from the group consisting of H, OH, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.2-6 alkene, C.sub.6-12 aryl, C.sub.1-6 hydroxyalkyl, C.sub.1-6 thioalkyl, C.sub.2-12 alkoxyalkyl, C.sub.3-20 heteroaromatic, and combinations thereof, wherein R may further contain one or more atoms of a non-carbon element such as Si, Ge, Sn, P, and the like; and Y is a cation, are prepared by reacting silica or alumina with a diol, in the presence of a base, while removing water formed during the reaction. Methods for producing such complexes starting with silica or alumina, and methods for converting such complexes into other silicon or aluminum-containing compounds, are disclosed.Type: GrantFiled: April 13, 1990Date of Patent: March 24, 1992Assignee: Washington Research FoundationInventors: Richard M. Laine, Kay A. Youngdahl, Paola Nardi
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Patent number: 5091378Abstract: Compounds which are useful as inhibitors of cholesterol biosynthesis and thus as hypocholesteroleumic agents are provided which have the structure ##STR1## wherein R is OH, or salts thereof or lower alkoxy; R.sup.x is H or alkyl;X is --CH.sub.2 --, --CH.sub.2 --CH.sub.2 --, --CH.dbd.CH--, --C.tbd.C--, --CH.sub.2 CH.sub.2 CH.sub.2 -- or --CH.sub.2 O-- (where O is linked to Z);Z is a hydrophobic anchor, such as ##STR2## wherein the dotted lines represent optional double bonds. New intermediates used in preparing the above compounds, pharmaceutical compositions containing such compounds and a method for using such compounds to inhibit cholesterol biosynthesis are also provided.Type: GrantFiled: April 18, 1988Date of Patent: February 25, 1992Assignee: E. R. Squibb & Sons, Inc.Inventors: Donald S. Karanewsky, Michael C. Badia, Scott A. Biller, Eric M. Gordon, Michael J. Sofia
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Patent number: 5055471Abstract: This invention relates to derivatives of propanoic acid of the formula ##STR1## Useful as fungicides, insecticides and miticides, to processes for preparing them, to compositions containing them, and to methods of using them to combat fungi, especially fungal infections of plants, and to kill or control insects and mites.Type: GrantFiled: November 15, 1989Date of Patent: October 8, 1991Assignee: Imperial Chemical Industries PLCInventors: Paul J. de Fraine, Anne Martin
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Patent number: 5047557Abstract: Compounds of the formula I ##STR1## in which Me is Ti, Zr or Hf, R.sub.1 is a group transferable to aldehyde, keto or imine groups, for example methyl, allyl, vinyl or the radical of an enol or enamine, R.sub.2 is, for example, cyclopentadienyl, R.sub.3 and R.sub.4 are, for example, H or alkyl, R.sub.5 is, for example, phenyl and the C(1) and C(2) atoms are chiral and have predominantly one configuration, are suitable for use as chiral reactants for aldehydes, ketones and imines for the preparation of both enantiomers of secondary or tertiary alcohols or tertiary amines.Type: GrantFiled: February 16, 1990Date of Patent: September 10, 1991Assignee: Ciba-Geigy CorporationInventors: Andreas Hafner, Rudolf Duthaler, Guido Bold
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Patent number: 4963538Abstract: Novel HMG-CoA reductase inhibitors are useful as antihypercholesterolemic agents and are represented by structural formulae (I) or (II): ##STR1## wherein position 5 of the polyhydronaphthyl ring is singly or doubly bonded to oxygen or incorporated into a C.sub.3-7 carbocyclic ring.Type: GrantFiled: March 13, 1989Date of Patent: October 16, 1990Assignee: Merck & Co., Inc.Inventors: Mark E. Duggan, George D. Hartman
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Patent number: 4963537Abstract: Novel labdanes, intermediates and processes for the preparation thereof, and methods for reducing intraocular pressure utilizing compounds or compositions thereof are disclosed.Type: GrantFiled: April 26, 1989Date of Patent: October 16, 1990Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Raymond W. Kosley, Jr., Robert J. Cherill
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Patent number: 4963536Abstract: A compound of the formula: ##STR1## wherein R.sup.1 -A- is a group of the formula: ##STR2## in which R.sup.1 is aryl or a heterocyclic group, each of which may be substituted with substituent(s) selected from the group consisting of lower alkyl, lower alkoxy, lower alkylthio, halo(lower)alkyl, acyl, acylamino and halogen, or lower alkyl which may be substituted with a heterocyclic group optionally substituted with acyl, andX is O or S, andR.sup.2 is hydrogen or lower alkyl, provided that when R.sup.1 is lower alkyl, thenR.sup.1 -A- is a group of the formula: ##STR3## in which R.sup.1 and X are each as defined above, processes for the preparation thereof and pharmaceutical composition comprising the same.Type: GrantFiled: April 6, 1989Date of Patent: October 16, 1990Assignee: Fujisawa Pharmaceutical Company, Ltd.Inventors: Teruo Oku, Eishiro Todo, Chiyoshi Kasahara, Katsuya Nakamura, Hiroshi Kayakiri, Masashi Hashimoto
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Patent number: 4933472Abstract: Substituted aminomethylenebis(phosphonic acid) derivatives represented by the general formula: ##STR1## in which R.sup.1, R.sup.2 R.sup.3 and R.sup.4 may be the same or different, each represents a hydrogen atom or a lower alkyl group; "m" is zero or represents an integer from 1 to 4; and a ring "A" represents a cycloalkenyl group having 5 to 8 carbon atoms, a bicycloheptyl group, a bicycloheptenyl group or a saturated heterocyclic group having 4 to 7 carbon atoms and containing an oxygen atom, a sulfur atom, a sulfinyl group (--SO--) or a sulfonyl group (--SO.sub.2 --),or pharmaceutically acceptable salts thereof.Type: GrantFiled: April 5, 1989Date of Patent: June 12, 1990Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Yasuo Isomura, Makoto Takeuchi, Shuichi Sakamoto, Tetsushi Abe
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Patent number: 4931568Abstract: Thiophene ethers having relatively large side chains can be easily obtained by reacting 2-, 3-, 2,3-, 2,4- or 3,4-C.sub.1 -C.sub.3 -alkoxythiophenes in the presence of an acid catalyst with a compound containing an OH group. The novel thiophene ethers are suitable as monomers for electrically conducting polymers.Type: GrantFiled: February 9, 1989Date of Patent: June 5, 1990Assignee: Hoechst AktiengesellschaftInventors: Peter Wegener, Michael Feldhues, Heinz Litterer
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Patent number: 4927835Abstract: Compounds of the formula (I): ##STR1## or a pharmaceutically acceptable salt thereof, wherein: R.sup.1 is cycloalkyl of 5 to 7 carbon atoms; aryl of 6 to 10 carbon atoms unsubstituted or substituted by straight or branched chain alkyl of 1 to 4 carbon atoms, halo or trifluoromethyl; or ##STR2## wherein A is oxygen, sulfur or NR.sup.5, wherein R.sup.5 is hydrogen, straight or branched chain alkyl of 1 to 4 carbon atoms or halo, and R.sup.6 is hydrogen, straight or branched chain alkyl of 1 to 4 carbon atoms or halo;R.sup.2 is straight or branched chain alkyl of 1 to 4 carbon atoms or cycloalkyl of 5 to 7 carbon atoms; andR.sup.3 and R.sup.4 are the same or different and each is hydrogen; straight or branched chain alkyl of 1 to 8 carbon atoms unsubstituted or substituted by hydroxy, acyloxy of 2 to 5 carbon atoms, carboxyl or carbamoyl;are useful for treating pain, inflammation and fever in humans and animals.Type: GrantFiled: March 1, 1989Date of Patent: May 22, 1990Assignee: Nippon Shinyaku Co., Ltd.Inventors: Masahiro Kise, Yoshihiko Yoshimoto, Hiroshi Fujisawa, Yasuo Sasaki, Shoji Yasufuku
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Patent number: 4880828Abstract: A new class of 2-(tetrahydro-2-theinyl)phenyl esters of phosphorothioic acid is disclosed. This class of compounds is an effective pesticide and finds particular application as an insecticide. A class of pesticidal compositions employing these compounds in combination with a carrier therefor is also set forth.Type: GrantFiled: January 29, 1988Date of Patent: November 14, 1989Assignees: Uniroyal Chemical, Inc., Uniroyal Chemical Ltd./LteeInventors: Anupama Mishra, Richard C. Moore
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Patent number: 4874846Abstract: Process for the preparation of aryloxy-benzoic acids containing a sulphonamide group by the direct reaction of a phenoxy-benzoic acid with a sulphonamide, in the presence of a halogenating agent such as P(O)Cl.sub.3.Type: GrantFiled: May 26, 1987Date of Patent: October 17, 1989Assignee: Rhone-Poulenc Agrochimie S.A.Inventor: Alain Chene
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Patent number: 4857513Abstract: A compound of the formula: ##STR1## wherein R.sup.1 --A-- is a group of the formula: ##STR2## in which R.sup.1 is aryl or a heterocyclic group, each of which may be substituted with substituent(s) selected from the group consisting of lower alkyl, lower alkoxy, lower alkylthio, halo(lower)alkyl, acyl, acylamino and halogen, or lower alkyl which may be substituted with a heterocyclic group optionally substituted with acyl, andX is O or S, andR.sup.2 is hydrogen or lower alkyl, provided that when R.sup.1 is lower alkyl, thenR.sup.1 --A-- is a group of the formula: ##STR3## in which R.sup.1 and X are each as defined above, and pharmaceutically acceptable salts thereof, processes for the preparation thereof and pharmaceutical composition comprising the same.Type: GrantFiled: April 24, 1987Date of Patent: August 15, 1989Assignee: Fujisiwa Pharmaceutical Co., Ltd.Inventors: Teruo Oku, Eishiro Todo, Chiyoshi Kasahara, Katsuya Nakamura, Hiroshi Kayakiri, Masashi Hashimoto