Chalcogen Bonded Directly To Ring Carbon Of The Six-membered Hetero Ring Patents (Class 546/24)
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Patent number: 5304549Abstract: Compounds of the formula ##STR1## wherein A is the group ##STR2## R.sup.1 is hydrogen, amino, protected amino, acylamino or lower alkyl optionally substituted by aryl, hydroxy, protected hydroxy, amino, protected amino, acylamino, maleimido, succinimido, naphthalimido, 2,3-dihydro-1,3-dioxo-1H-benz[d,e]isoquinol-2-yl, carboxy, protected carboxy, carbamoyl, mono(lower alkyl)carbamoyl, di(lower alkyl)carbamoyl, di(lower alkyl)amino, carboxy-lower alkanoylamino, pyrrolidino or morpholino; R.sup.2 is hydrogen or lower alkyl optionally substituted by aryl, amino, protected amino, di(lower alkyl)- amino, guanidino, carboxyl, protected carboxyl, carbamoyl, mono(lower alkyl) carbamoyl, di(lower alkyl)carbamoyl, di(lower alkoxy)phosphinyl, dihydroxyphosphinyl, pyrrolidino, piperidino or morpholino; R.sup.3 is hydrogen or lower alkyl optionally substituted by hydroxy, protected hydroxy, amino or protected amino; R.sup.4 is hydrogen, hydroxy, lower alkoxy or benzyloxy; and R.sup.Type: GrantFiled: January 21, 1992Date of Patent: April 19, 1994Assignee: Hoffmann-La Roche Inc.Inventors: Michael J. Broadhurst, Paul A. Brown, William H. Johnson, Geoffrey Lawton
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Use of pyridoxine derivatives in the prevention and treatment of hyperlipidaemia and atherosclerosis
Patent number: 5288716Abstract: A method for prevention of atherosclerosis or for treatment of hyperlipidaemia or atherosclerosis comprises administering one of more pyridoxine derivatives to a host in need thereof.Type: GrantFiled: June 15, 1989Date of Patent: February 22, 1994Inventor: Ulrich Speck -
Patent number: 5280022Abstract: A compound of the formula (I): ##STR1## wherein W is a group of the formula:A--O--(CH.sub.2 .sub.n --wherein A is a cyclic group which may be substituted, n is an of 2 to 10, or W is a group of the formula:R.sup.1 --X--(CH.sub.2).sub.n' --wherein R.sup.1 is an alkyl group which may be substituted, X is an oxygen atom or a sulfur atom which may be oxidized, n' is an integer of 4 to 10; R.sup.2 is a hydrogen atom or a lower alkanoyl group; R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are the same or different and are a hydrogen atom or a lower alkyl group, or a salt thereof, is useful as a bone resorption inhibitor.Type: GrantFiled: December 18, 1991Date of Patent: January 18, 1994Assignee: Takeda Chemical Industries, Ltd.Inventors: Takashi Sohda, Shigehisa Taketomi
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Patent number: 5250549Abstract: Sulfonamide derivatives of the general formula (I): ##STR1## wherein preferably R.sup.1 represents a lower alkoxy group, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are as defined in the specification, A and B may be the same or different from each other and each represents .dbd.N-- or .dbd.CH--, E represents an aromatic 6-membered cyclic group, which may have 1 or 2 nitrogen atoms in the ring, and may be substituted with 1 to 3 substituents which may be the same or different from one another with the proviso that a combination of R.sup.1 which is a hydrogen atom, lower alkyl group, nitro group or amino group which may be protected, R.sup.2 and R.sup.3 which are each a hydrogen atom, A and B which are each .dbd.CH-- and E which is a phenyl group which may be substituted with 1 to 3 substituents G which may be the same or different from one another is excluded, or pharmacologically acceptance salts of them.Type: GrantFiled: August 8, 1991Date of Patent: October 5, 1993Assignee: Eisai Co., Ltd.Inventors: Hiroshi Yoshino, Norihiro Ueda, Hiroyuki Sugumi, Jun Niijima, Yoshihiko Kotake, Toshimi Okada, Nozomu Koyanagi, Tatsuo Watanabe, Makoto Asada, Kentaro Yoshimatsu, Atsumi Iijima, Takeshi Nagasu, Kappei Tsukahara, Kyosuke Kitoh
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Patent number: 5234917Abstract: Angiotensin II receptor antagonists having the formula: ##STR1## which are useful in regulating hypertension and in the treatment of congestive heart failure, renal failure, and glaucoma pharmaceutical compositions including these antagonists, and methods of using these compounds to produce angiotensin II receptor antagonism in mammals.Type: GrantFiled: November 30, 1990Date of Patent: August 10, 1993Inventors: Joseph A. Finkelstein, Judith Hempel, Richard M. Keenan, James Samanen, Joseph Weinstock
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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: 5223243Abstract: N,N'-bis-(pyridoxal-5-phosphate)-alkylenediamine-N,N'-diacetic acids, N,N'-bis-(pyridoxal-5-phosphate)-1,2-cycloalkylenediamine-N,N'diacetic acids, and N,N'-bis-(pyridoxal-5-phosphate)-1,2-arylenediamine-N,N'diacetic acids, the corresponding monophosphate compounds and monoacetic acid compounds, and their salts and esters form stable, highly soluble chelates with paramagnetic metal ions, and are highly effective NMRI contrast agents. Preferred contrast agents are paramagnetic ion chelates of N,N'-bis-(pyridoxal-5-phosphate)ethylenediamine-N,N'-diacetic acid, N,N'-bis-(pyridoxal-5-phosphate)trans-1,2-cyclohexylenediamine-N,N'-diacet ic acid, N,N'-bis-(pyridoxal-5-phosphate)trans-1,2-arylenediamine-N,N'-diacetic acid, and the soluble calcium salts thereof.Type: GrantFiled: August 20, 1990Date of Patent: June 29, 1993Assignee: Salutar, Inc.Inventors: Scott M. Rocklage, Steven C. Quay
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Patent number: 5220021Abstract: Unsaturated geminal phosphonates (III) ##STR1## either as the esters, free acids or salts are useful in the treatment of arthritis.Type: GrantFiled: September 6, 1991Date of Patent: June 15, 1993Assignee: The Upjohn CompanyInventors: Colin J. Dunn, Richard A. Nugen
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Patent number: 5213607Abstract: 2-(1-Substituted-2-imidazolin-2-yl)benzoic and nicotinic acids, and derivatives thereof, which are effective in the control of undesirable plant species are described. Also described are a method for the herbicidal use of the compounds and a method for their preparation.Type: GrantFiled: September 19, 1991Date of Patent: May 25, 1993Assignee: American Cyanamid CompanyInventor: Michael A. Guaciaro
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Patent number: 5130437Abstract: Manganese(II) chelates of N,N'-bis-(pyridoxal)alkylenediamine-N,N'-diacetic acids, N,N'-bis-(pyridoxal)-1,2-cycloalkylenediamine-N,N'-diacetic acids, N,N'-bis-(pyridoxal)-1,2-arylenediamine-N,N'-diacetic acids, N,N'-bis-(pyridoxal)alkylenediamine-N-acetic acids, N,N'-bis-(pyridoxal)-1,2-cycloalkylenediamine-N-acetic acids, N,N'-(pyridoxal)-1,2-arylenediamine-N-acetic acids, and their salts are highly stable, superior NMRI contrast agents. They maintain the manganese(II) ion in the +2 valence state. Preferred contrast agents are manganese(II) ion chelates of N,N'-bis-(pyridoxal)ethylenediamine-N,N'-diacetic acid, N,N'-bis-(pyridoxal)trans-1,2-cyclohexylenediamine-N,N'-diacetic acid, and the salts and esters thereof.Type: GrantFiled: September 6, 1990Date of Patent: July 14, 1992Assignee: Salutar, Inc.Inventors: Scott M. Rocklage, Steven C. Quay
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Patent number: 5130431Abstract: N,N'-bis-(pyridoxal-5-phosphate)-alkylenediamine-N,N'-diacetic acids, N,N'-bis-(pyridoxal-5-phosphate)-1,2-cycloalkylenediamine-N,N'-diacetic acids, and N,N'-bis-(pyridoxal-5-phosphate)-1,2-arylenediamine-N,N'-diacetic acids, the corresponding monophosphate compounds and monoacetic acid compounds, and their salts and esters form stable, highly soluble chelates with paramagnetic metal ions, and are highly effective NMRI contrast agents. Preferred contrast agents are paramagnetic ion chelates of N,N'-bis-(pyridoxal-5-phosphate)ethylenediamine-N,N'-diacetic acid, N,N'-bis-(pyridoxal-5-phosphate)trans-1,2-cyclohexylenediamine-N,N'-diacet ic acid, N,N'-bis-(pyridoxal-5-phosphate)trans-1,2-arylenediamine-N,N'-diacetic acid, and the soluble calcium salts thereof.Type: GrantFiled: July 6, 1990Date of Patent: July 14, 1992Assignee: Salutar, Inc.Inventors: Scott M. Rocklage, Steven C. Quay
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Patent number: 5106982Abstract: Novel compounds having the general formula ##STR1## wherein A and A' are amino acid residues linked by a peptidal bond to the nucleus, are disclosed. These compounds are CNS agents with anxiogenic activity.Type: GrantFiled: December 10, 1990Date of Patent: April 21, 1992Assignee: E. R. Squibb & Sons, Inc.Inventors: Callixtus E. Ita, Peter Egli
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Patent number: 5091169Abstract: N,N'-bis-(pyridoxal-5-phosphate)-alkylenediamine-N,N'-diacetic acids, N,N'-bis-(pyridoxal-5-phosphate)-1,2-cycloalkylenediamine-N,N'-diacetic acids, and N,N'-bis-(pyridoxal-5-phosphate)-1,2-arylenediamine-N,N'-diacetic acids, the corresponding monophosphate compounds and monoacetic acid compounds, and their salts and esters form stable, highly soluble chelates with paramagnetic metal ions, and are highly effective NMRI contrast agents. Preferred contrast agents are paramagnetic ion chelates of N,N'-bis-(pyridoxal-5-phosphate)ethylenediamine-N,N'-diacetic acid, N,N'-bis-(pyridoxal-5-phosphate)trans-1,2-cyclohexylenediamine-N,N'diaceti c acid, N,N'-bis-(pyridoxal-5-phosphate)trans-1,2-arylenediamine-N,N'-diacetic acid, and the soluble calcium salts thereof.Type: GrantFiled: June 23, 1989Date of Patent: February 25, 1992Assignee: Salutar, Inc.Inventors: Scott M. Rocklage, Steven C. Quay
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Patent number: 5075324Abstract: 1,4-dihydropyridines of formula I ##STR1## wherein X is --CO.sub.2 R.sub.1, cyano, nitro, --COCH.sub.3 ; each of R and R.sub.1, which are the same or different, is a primary, secondary or tertiary, saturated or unsaturated, linear or branched C.sub.1 -C.sub.6 alkyl group optionally substituted by one or more hydroxy, C.sub.1 -C.sub.7 -monoalkylamino, di-C.sub.1 -C.sub.7 -alkylamino, benzylamino, C.sub.1 -C.sub.6 -alkoxy, phenoxy groups which are optionally substituted; R.sub.2 is hydrogen; R.sub.3 is hydrogen or hydroxy, --OCOR.sub.5, OSO.sub.2 R.sub.6, azide, amino, --NHPO(OR.sub.7).sub.2, --NHCOR.sub.5, C.sub.1 -C.sub.4 -alkoxy or fluorine, chlorine, bromine or iodine, SH, SCOR.sub.6 or C.sub.1 -C.sub.6 -alkylthio, phenylthio or benzylthio; R.sub.4 is an optionally substituted aromatic or an optionally substituted 5- or 6-membered heteroaromatic group; Y is one or more substituents, which may be the same or different, selected from C.sub.1 -C.sub.4 -alkoxy, halogen, nitro, cyano, C.sub.1 -C.sub.Type: GrantFiled: June 22, 1989Date of Patent: December 24, 1991Assignee: Boehringer Biochemia Robin S.p.A.Inventors: Marco Frigerio, Andrea Zaliani, Carmelo A. Gandolfi, Mauro Germini, Odoardo Tofanetti, Sergio Tognella
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Patent number: 5068394Abstract: Herbicidal (hetero)aryloxynaphthalene derivatives of the formula ##STR1## in which X is N or --C--R.sup.5,R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen or halogen or R.sup.1 may be cyano or trifluoromethyl,R.sup.3 is halogen, trifluoromethyl, trifluoromethoxy, trifluoromethylthio or trifluoromethylsulphonyl,Y is optionally halogen-substituted alkanediyl or alkenediyl, andZ is CN or --CC--Z', whereZ' is halogen, hydroxyl, amine, alkoxy, or the like.Intermediates of the formula ##STR2## are also new.Type: GrantFiled: October 19, 1989Date of Patent: November 26, 1991Assignee: Bayer AktiengesellschaftInventors: Roland Andree, Michael Haug, Hans-Joachim Santel, Robert R. Schmidt, Harry Strang
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Patent number: 5062881Abstract: 2-(1-Substituted-2-imidazolin-2-yl)benzoic and nicotinic acids, and derivatives thereof, which are effective in the control of undesirable plant species are described. Also described are a method for the herbicidal use of the compounds and a method for their preparation.Type: GrantFiled: December 20, 1989Date of Patent: November 5, 1991Assignee: American Cyanamid CompanyInventor: Michael A. Guaciaro
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Patent number: 5061813Abstract: Novel compounds are disclosed having the formula ##STR1## and R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are as defined herein. These compounds are useful, for example, as cardiovascular agents and especially as anti-ischemic agents.Type: GrantFiled: April 2, 1990Date of Patent: October 29, 1991Assignee: E. R. Squibb & Sons, Inc.Inventor: Karnail Atwal
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Patent number: 5036152Abstract: Novel alkoxycarbonylalkylphospholipids, alkylaminocarbonylalkylphospholipids, processes for the preparation thereof, and methods for treating inflammation utilizing compounds or compositions thereof are disclosed.Type: GrantFiled: September 5, 1989Date of Patent: July 30, 1991Assignee: Hoechst-Roussel Pharmaceuticals IncorporatedInventors: Nicholas J. Hrib, Kirk D. Shoger, John J. Tegeler
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Patent number: 5019565Abstract: Fungicidal pyridyl imidates having the general structural formula ##STR1## wherein R is selected from the group consisting of C.sub.1 -C.sub.16 alkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.2 -C.sub.8 alkenyl, C.sub.2 -C.sub.8 substituted alkenyl, C.sub.3 -C.sub.4 carboalkoxyalkyl, aryl, arylalkyl having C.sub.1 -C.sub.3 alkyl, substituted aryl and arylalkyl wherein the substituents are -Cl, -Br, -F and -NO.sub.2, furfuryl pyridyl, C.sub.1 -C.sub.6 alkoxyl substituted thiophosphorus, and ##STR2## wherein R.sub.3 and R.sub.4 are C.sub.1 -C.sub.10 alkyl and can form a heterocyclic ring, R.sub.1 is selected from the group consisting of halogen, C.sub.1 -C.sub.3 alkoxy and C.sub.1 -C.sub.3 haloalkoxy, R.sub.2 is selected from the group consisting of methyl and hydrogen, and X is S or O; and fungicidally acceptable organic and inorganic salts thereof.Type: GrantFiled: December 4, 1989Date of Patent: May 28, 1991Assignee: ICI Americas Inc.Inventors: Don R. Baker, Keith H. Brownell
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Patent number: 5015678Abstract: The Michael addition products of N-hydroxy hindered amines with alpha,beta-unsaturated carbonyl compounds including derivatives of esters, amids, imides and anhydrides are effective stabilizers for protecting organic polymers from the deleterious effects of actinic light.Type: GrantFiled: February 14, 1990Date of Patent: May 14, 1991Assignee: Ciba-Geigy CorporationInventors: Raymond Seltzer, James P. Galbo, Ramanathan Ravichandran
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Patent number: 5006651Abstract: The invention relates compounds of the formula ##STR1## wherein R.sup.1 -R.sup.5 and X have the significance given in the description, and their pharmaceutically acceptable salts. The compounds of formula I inhibit the enzyme collagenase and can be used in the form of medicaments for the control or prevention of degenerative joint diseases such as rheumatoid arthritis and osteoarthritis.Type: GrantFiled: September 22, 1989Date of Patent: April 9, 1991Assignee: Hoffman-La Roche Inc.Inventors: Michael J. Broadhurst, Balraj K. Handa, William H. Johnson, Geoffrey Lawton, Peter J. Machin
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Patent number: 5006658Abstract: A compound of Formula I or a salt thereof:Ar--Q--(CH.sub.2).sub.m --A--CH.sub.2).sub.n (CE.sup.1 .dbd.CE.sup.2).sub.a CE.sup.3 .dbd.CE.sup.4 CXNR.sup.1 R.sup.2 (1)whereAr is a 6-membered heteroaromatic ring containing, as the heteroatom or heteroatoms, one or two nitrogen atoms and is optionally substituted by one or more of halogen, cyano, C.sub.1-6 -alkyl (optionally substituted by halogen), or C.sub.1-6 -alkoxy (optionally substituted by one or more of halogen or C.sub.1-6 -alkyl), or RS(O).sub.x where x is 0, 1 or 2 and R is C.sub.1-6 -alkyl optionally substituted by one or more halogen atoms,Q is --CH.sub.2 -- or --O--,m and n are each independently 0 to 7,A is --CH.sub.2 -- or --O--,a is 0 or 1,E.sup.1 to E.sup.4 are independently hydrogen, C.sub.1-4 -alkyl or halo-C.sub.1-4 -alkyl or halogen,X is oxygen or sulphur, andR.sup.1 and R.sup.2 are independently hydrogen, C.sub.1-6 -alkyl or C.sub.3-6 -cycloalkyl, either being optionally substituted by one or more of the C.sub.1-6 -alkyl, C.sub.Type: GrantFiled: November 25, 1987Date of Patent: April 9, 1991Assignee: The Wellcome Foundation Ltd.Inventor: Robert J. Blade
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Patent number: 4992554Abstract: N,N'-bis-(pyridoxal-5-phosphate)-alkylenediamine-N,N'-diacetic acids, N,N'-bis-(pyridoxal-5-phosphate)-1,2-cycloalkylenediamine-N,N'-diacetic acids, and N,N'-bis-(pyridoxal-5-phosphate)-1,2-arylenediamine-N,N'-diacetic acids, the corresponding monophosphate compounds and monoacetic acid compounds, and their salts and esters form stable, highly soluble chelates with paramagnetic metal ions, and are highly effective NMRI contrast agents. Preferred contrast agents are paramagnetic ion chelates of N,N'-bis-(pyridoxal-5-phosphate)ethylenediamine-N,N'-diacetic acid, N,N'-bis-(pyridoxal-5-phosphate)trans-1,2-cyclohexylenediamine-N,N'-diacet ic acid, N,N'-bis-(pyridoxal-5-phosphate)trans-1,2-arylenediamine-N,N'-diacetic acid, and the soluble calcium salts thereof.Type: GrantFiled: June 23, 1989Date of Patent: February 12, 1991Assignee: Salutar, Inc.Inventors: Scott M. Rocklage, Steven C. Quay
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Patent number: 4992555Abstract: N,N'-bis-(pyridoxal-5-phosphate)-alkylenediamine-N,N'-diacetic acids, N,N'-bis-(pyridoxal-5-phosphate)-1,2-cycloalkylenediamine-N,N'-diacetic acids, and N,N'-bis-(pyridoxal-5-phosphate)-1,2-arylenediamine-N,N'-diacetic acids, the corresponding monophosphate compounds and monoacetic acid compounds, and their salts and esters form stable, highly soluble chelates with paramagnetic metal ions, and are highly effective NMRI contrast agents. Preferred contrast agents are paramagnetic ion chelates of N,N'-bis-(pyridoxal-5-phosphate)ethylenediamine-N,N'-diacetic acid, N,N'-bis-(pyridoxal-5-phosphate)trans-1,2-cyclohexylenediamine-N,N'-diacet ic acid, N,N'-bis-(pyridoxal-5-phosphate)trans-1,2-arylenediamine-N,N'-diacetic acid, and the soluble calcium salts thereof.Type: GrantFiled: June 23, 1989Date of Patent: February 12, 1991Assignee: Salutar, Inc.Inventors: Scott M. Rocklage, Steven C. Quay
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Patent number: 4988681Abstract: A phosphinic acid derivative represented by the general formula [I], or a pharmaceutically acceptable salt thereof, ##STR1## wherein R.sup.1 represents an alkyl, cycloalkyl or aralkyl group which may be substituted; R.sup.2 and R.sup.5 may be identical or different, and each represents a hydrogen atom, or an ester residue capable of forming a non-toxic ester hydrolyzable in vivo; and A represents a group of the formula ##STR2## wherein R.sup.3 represents an alkyl group, a group of the formula ##STR3## wherein R.sup.30 represents a halogen atom, a carboxyl group, a hydroxyl group, a cycloalkyl group which may be substituted, an aryl group which may be substituted, an arylthio group, a heteroarylthio group which may be substituted, an alkylthio group which may be substituted, an amino group which may be substituted, or a lower alkoxycarbonyl group; R.sup.Type: GrantFiled: June 22, 1989Date of Patent: January 29, 1991Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Kiyofumi Ishikawa, Takehiro Fukami, Hiroshi Naganuma, Kyoko Nakamichi
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Patent number: 4968695Abstract: Pest-combating agents, in particular as insecticides which substituted nitroalkenes of the formula ##STR1## in which m represents 0, 1 or 2,A represents alkanediyl,R.sup.1 represents an optionally substituted five-or six-membered heterocyclic grouping,R.sup.2 represents hydrogen or alkyl,R.sup.3 represents hydrogen or optionally substituted alkyl, alkenyl, alkinyl, benzyl, furyl, furylmethyl, thenyl, thienyl or pyridyl,R.sup.4 represents optionally substituted phenyl, pyrimidinyl, imidazolyl or triazolyl andX represents oxygen, sulphur or the grouping N--R.sup.5,whereinR.sup.5 represents hydrogen, optionally substituted alkyl, alkenyl, alkinyl, or benzyl, formyl, or optionally substituted alkylcarbonyl, cycloalkylcarbonyl, alkenylcarbonyl, phenylcarbonyl or naphthylcarbonyl.Type: GrantFiled: May 11, 1988Date of Patent: November 6, 1990Assignee: Bayer AktiengesellschaftInventors: Hilmar Wolf, Benedikt Becker, Bernhard Homeyer, Wilhelm Stendel
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Patent number: 4959480Abstract: Novel pyrazoloazole couplers comprise an aryl or heterocyclic group having, in at least one of the ortho positions to the carbon atom (A) that is bonded to the pyrazoloazole nucleus, a substituent (B) that enables the pyrazoloazole coupler to form a magenta dye that has increased stability and has absorption controllably shifted, that is shifted hypsochromically relative to a dye formed from a similar coupler lacking substituent (B). These couplers are useful in photographic silver halide materials and processes.Type: GrantFiled: March 9, 1988Date of Patent: September 25, 1990Assignee: Eastman Kodak CompanyInventors: Sharon E. Normandin, Arlyce T. Bowne, Nigel E. Milner, David Clarke
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Patent number: 4948414Abstract: There are described novel 3-fluoropyridyl-2-oxy derivatives having a herbicidal action and an action reducing the growth of grasses, which compounds correspond to the formula I ##STR1## wherein X is halogen or the trifluoromethyl group, andZ is an alkanoic acid derivative which is more precisely described in the specification.These compounds are suitable for the selective control of weeds in crops of cultivated plants, or for the reduction of the growth of grasses.Type: GrantFiled: December 12, 1988Date of Patent: August 14, 1990Assignee: Ciba-Geigy CorporationInventors: Rolf Schurter, Peter J. Diel
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Patent number: 4933475Abstract: Compounds having the formula ##STR1## R.sub.1 is hydrogen, benzyl or alkanoyl, X is C.sub.2-4 alkylene; andZ-W is alkyl, phenylalkyl or pyridylalkyl which can have an oxygen atom as part of the alkyl chain and their use as CNS agents, antidiarrheals and antiemetics. Processes for their preparation and intermediates therefor are described.Type: GrantFiled: February 28, 1989Date of Patent: June 12, 1990Assignee: Pfizer, Inc.Inventors: Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4933456Abstract: N,N'-bis-(pyridoxal-5-phosphate)-alkylenediamine-N,N'-diacetic acids, N,N'-bis-(pyridoxal-5-phosphate)-1,2-cycloalkylenediamine-N,N'-diacetic acids, and N,N'-bis-(pyridoxal-5-phosphate)-1,2-arylenediamine-N,N'-diacetic acids, the corresponding monophosphate compounds and monoacetic acid compounds, and their salts and esters form stable, highly soluble chelates with paramagnetic metal ions, and are highly effective NMRI contrast agents. Preferred contrast agents are paramagnetic ion chelates of N,N'-bis-(pyridoxal-5-phosphate)ethylene-diamine-N,N'-diacetic acid, N,N'-bis-(pyridoxal-5-phosphate)trans-1,2-cyclohexylenediamine-N,N'-diacet ic acid, N,N'-bis-(pyridoxal-5-phosphate)trans-1,2-arylenediamine-N,N'-diacetic acid, and the soluble calcium salts thereof.Type: GrantFiled: May 8, 1987Date of Patent: June 12, 1990Assignee: Salutar, Inc.Inventors: Scott M. Rocklage, Steven C. Quay
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Patent number: 4927925Abstract: Compounds of formula (I) ##STR1## in which R.sub.1 is hydrogen, O.sup.., CN, NO, cyanomethyl, C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.12 -alkenyl or C.sub.3 -C.sub.12 -alkynyl subject to the proviso that the carbon atom attached to the nitrogen atom is a primary carbon atom, C.sub.7 -C.sub.12 -aralkyl, C.sub.1 -C.sub.12 -acyl, 2,3-epoxypropyl, OH-monosubstituted C.sub.2 -C.sub.6 -alkyl or 2,3-dihydroxypropyl, R.sub.2 is hydrogen, C.sub.1 -C.sub.18 -alkyl, C.sub.5 -C.sub.18 -cycloalkyl, C.sub.6 -C.sub.18 -aryl or C.sub.7 -C.sub.18 -aralkyl, R.sub.3 is C.sub.6 -C.sub.18 -aryl or a group of the formula (II) ##STR2## in which R.sub.1 is as defined above, n is an integer from 1 to 4 and R.sub.4 is an organic or inorganic radical of a valency equal to n are useful for stabilizing organic material against oxidative, thermal and/or light induced degradation.Type: GrantFiled: October 13, 1988Date of Patent: May 22, 1990Assignee: Ciba-Geigy CorporationInventors: Giuseppe Cantatore, Valerio Borzatta
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Patent number: 4876247Abstract: The invention relates to methylenediphosphonic acid derivatives of the formula: ##STR1## in which: R.sub.1 represents:a C.sub.1 -C.sub.6 alkyl group,a C.sub.5 -C.sub.7 cycloalkyl group,a phenyl group optionally monosubstituted or polysubstituted by a halogen, a C.sub.1 -C.sub.6 alkyl group or a trifluoromethyl group, ora 5-membered or 6-membered heterocycle containing 1 or 2 heteroatoms chosen from nitrogen and sulfur,Alk denotes a linear or branched C.sub.1 -C.sub.6 alkylene group,R.sub.2 represents hydrogen, a C.sub.1 -C.sub.6 alkyl group or a --CONH.sub.2 group,R.sub.3 represents hydrogen, a C.sub.1 -C.sub.6 alkyl group, a benzyl group or a phenyl group optionally substituted by chlorine or methyl groups; or alternativelyR.sub.2 and R.sub.3, taken together, represent a (CH.sub.2).sub.m group, in which m=4 or 5, and finallyn represents 0 or the integer 1 or 2.These derivatives possess antirheumatic properties.Type: GrantFiled: October 30, 1987Date of Patent: October 24, 1989Assignee: SanofiInventors: Alain Barbier, Jean-Claude Breliere, Georges Garcia
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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: 4871720Abstract: Aromatically substituted azacycloalkylalkanediphosphonic acids of the formula ##STR1## in which R represents an aromatically substituted azacycloaliphatyl radical that is bonded to the group alk by way of a nitrogen atom and that optionally contains an additional nitrogen atom, and alk represents a divalent aliphatic radical, and their salts, can be used for the treatment of illnesses that can be attributed to calcium metabolism disorders. They are manufactured, for example, by reacting a compound of the formulaR--alk--X.sub.3 (IV)in which X.sub.3 represents carboxy, carbamoyl or cyano, with phosphorus acid and phosphorus trichloride and in an intermediate of the formula ##STR2## obtained by starting from compounds of the formula IV in which X.sub.3 represents cyano or carbamoyl and by working up by hydrolysis, or in a salt thereof, replacing the amino group by hydroxy by treatment with nitrous acid.Type: GrantFiled: November 16, 1987Date of Patent: October 3, 1989Assignee: Ciba-Geigy CorporationInventor: Knut A. Jaeggi
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Patent number: 4855309Abstract: The compounds of the formula (I) ##STR1## in which A denotes N or N.fwdarw.0,R denotes a radical of the formula R.sup.4 --CY.sup.1 --NR.sup.5 --CY.sup.2 --NR.sup.6 --, ##STR2## R.sup.1 denotes halogen, alkyl, alkenyl, alkynyl, alkoxy, alkoxycarbonyl or alkylcarbonyl, where these radicals may be halogenated, nitro, cyano or carboxyl, R.sup.2 denotes halogenated alkoxy, halogenated alkenyloxy or halogenated alkynloxy, R.sup.3 denotes halogen, n denotes 0, 1 or 2, m denotes 0, 1, 2 or 3, and p denotes 0 or 1, and also the salts thereof, are advantageously suitable for combating noxious insects, acarides, nematodes or mollusks.Type: GrantFiled: December 19, 1986Date of Patent: August 8, 1989Assignee: Hoechst AktiengesellschaftInventors: Volker Koch, Andreas Fuss, Werner Bonin, Werner Knauf, Anna Waltersdorfer
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Patent number: 4838923Abstract: An organo-phosphorus compound represented by the following formula (I) ##STR1## wherein X and Y are identical or different and each represents a hydrogen atom, a halogen atom, CF.sub.3 or an alkyl group having not more than 5 carbon atoms; Z represents CH or N; R.sup.1, R.sup.2 l and R.sup.3 l are identical or different and each represents a hydrogen atom or a lower alkyl group having 1 to 5 carbon atoms; and n is zero or 1. The compound is useful, as a herbicide, for eradicating weeds, especially narrow-leaved weeds.Type: GrantFiled: March 17, 1987Date of Patent: June 13, 1989Assignee: Teijin LimitedInventors: Shizuo Azuma, Toshiyuki Hiramatsu, Koji Nakagawa, Yataro Ichikawa
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Patent number: 4837327Abstract: Aryl difluoromethyl sulfone adds to alkehydes under phase transfer conditions to give novel substituted alcohols of the general formulaRCH(OH)CF.sub.2 SO.sub.2 Ar (I)wherein R is an aryl, cycloaliphatic, sec- or tert-aliphatic, or heterocyclic group and Ar is an aryl group. The substituted alcohols of formula I are of particular utility as intermediates in the synthesis of a variety of useful end products. For example, the products of formula I may be utilized in desulfonylation reactions, oxidation reactions and fluorination reactions.Type: GrantFiled: July 13, 1987Date of Patent: June 6, 1989Assignee: Ethyl CorporationInventor: G. Patrick Stahly
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Patent number: 4806604Abstract: The present invention discloses a new class of calcium chelating compounds which have a decreased affinity for calcium following illumination. These new compounds contain a photolabile nitrobenzyl derivative coupled to a tetracarboxylate Ca.sup.2+ chelating parent compound having the octacoordinate chelating groups characteristic of EGTA or BAPTA. However unlike EGTA or BAPTA-like compounds, in which the two halves of the chelator are linked by a simple 1,2-ethanediyl moiety, the compounds of the present invention modify the stereochemical conformation of this linkage by adding bulky substituents or incorporating the linkage into a carbocyclic or heterocyclic ring. In a first form, the new compounds are comprised of a BAPTA-like chelator coupled to a single 2-nitrobenzyl derivative, which in turn is a photochemical precursor of a 2-nitrosobenzophenone.Type: GrantFiled: May 13, 1987Date of Patent: February 21, 1989Assignee: Regents of the University of CaliforniaInventors: Roger Yonchien Tsien, Stephen R. Adams
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Patent number: 4803234Abstract: Compounds of formula (I) ##STR1## in which R.sub.1 is hydrogen, O.sup.., CN, NO, cyanomethyl, C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.12 -alkenyl or C.sub.3 -C.sub.12 -alkynyl subject to the proviso that the carbon atom attached to the nitrogen atom is a primary carbon atom, C.sub.7 -C.sub.12 -aralkyl, C.sub.1 -C.sub.12 -acyl, 2,3-epoxypropyl, OH-monosubstituted C.sub.2 -C.sub.6 -alkyl or 2,3-dihydroxypropyl, R.sub.2 is hydrogen, C.sub.1 -C.sub.18 -alkyl, C.sub.5 -C.sub.18 -cycloalkyl, C.sub.6 -Chd 18-aryl or C.sub.7 -C.sub.18 -aralkyl, R.sub.3 is C.sub.6 -C.sub.18 -aryl or a group of the formula (II) ##STR2## in which R.sub.1 is as defined above, n is an integer from 1 to 4 and R.sub.4 is an organic or inorganic radical of a valency equal to n are useful for stabilizing organic material against oxidative, thermal and/or light induced degradation.Type: GrantFiled: January 29, 1987Date of Patent: February 7, 1989Assignee: Ciba-Geigy CorporationInventors: Giuseppe Cantatore, Valerio Borzatta
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Patent number: 4798619Abstract: There are provided novel 2-(2-imidazolin-2-yl)pyridine and quinoline compounds, and a method for controlling a wide variety of annual and perennial plant species therewith.Type: GrantFiled: April 10, 1986Date of Patent: January 17, 1989Assignee: American Cyanamid Co.Inventor: Marinus Los
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Patent number: 4795815Abstract: 1,2,4-Trisubstituted diazolidinones are intermediates to bicyclic pyrazolidinone antimicrobial compounds.Type: GrantFiled: October 29, 1987Date of Patent: January 3, 1989Assignee: Eli Lilly and CompanyInventor: Robert J. Ternansky
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Patent number: 4790868Abstract: This invention relates to herbicidally active substituted benzoxazolone (or benzthiazolone) compounds and to the use of such compounds to control the growth of noxious plants, i.e., weeds.Type: GrantFiled: January 7, 1987Date of Patent: December 13, 1988Assignee: PPG Industries, Inc.Inventor: Donald R. Nielsen
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Patent number: 4791139Abstract: A compound of formula: ##STR1## wherein W represents one or more substituents selected from halo, alkyl, alkoxy, alkoxyalkyl, haloalkyl and haloalkoxy or W represents a bidentate group linking adjacent carbon atoms selected from alkylene and alkylenedioxy; Y is a group of formula ##STR2## wherein X is a group of formula --(CF.sub.2).sub.n R.sup.3, where R.sup.3 is selected from hydrogen, chloro and fluoro, and n is one or two, R.sup.1 is selected from hydrogen, chloro, fluoro and hydroxy and R.sup.2 is selected from methyl, cyano, ethynyl and hydrogen; Q is selected from carbon bearing a hydrogen atom and nitrogen; and Z represents one or more substituents selected from fluoro, benzyl, phenoxy, chlorophenoxy, fluorophenoxy and bromophenoxy, or any isomer thereof. Processes for preparing these compounds and intermediates for use therein, insecticidal compositions containing these compounds and the use thereof are also disclosed.Type: GrantFiled: February 25, 1987Date of Patent: December 13, 1988Assignee: Imperial Chemical Industries PLCInventors: Michael J. Bushell, Robin A. E. Carr
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Patent number: 4787929Abstract: Novel phenoxypropionyloxyalkanephosphonates of the formula ##STR1## in which R is optionally substituted alkyl andA is alkanediyl substituted by an optionally substituted pyridyl and use of such new compounds as herbicides.Type: GrantFiled: January 7, 1987Date of Patent: November 29, 1988Assignee: Bayer AktiengesellschaftInventors: Theodor Pfister, Heinz Forster, Ludwig Eue, Robert R. Schmidt, Hans-Joachim Santel
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Patent number: 4770692Abstract: Novel herbicidal and plant-growth regulating pyrazoles of the formula ##STR1## in which R.sup.1 represents hydrogen, alkyl or halogenoalkyl,R.sup.2 represents nitro or cyano,R.sup.3 represents optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkinyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted aralkyl or optionally substituted aryl,Ar represents phenyl which is substituted twice or more, or optionally substituted pyridyl, andY represents O, S, SO or SO.sub.2.Several intermediates therefor are also new.Type: GrantFiled: July 14, 1987Date of Patent: September 13, 1988Assignee: Bayer AktiengesellschaftInventors: Jorg Stetter, Reinhold Gehring, Otto Schallner, Hans-Joachim Santel, Robert R. Schmidt, Klaus Lurssen
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Patent number: 4770688Abstract: A 1-aryl-pyrazole of the formula ##STR1## in which R represents cyano or nitro,Ar represents in each case optionally substituted phenyl or pyridyl,X represents an azido group, or represents the radical ##STR2## and R.sup.1, R.sup.2 and R.sup.3 each independently represents alkyl, alkenyl, alkinyl, halogenoalkyl, alkoxy, alkoxyalkyl, cycloalkyl or cycloalkyloxy, or represents in each case optionally substituted aryl, aryloxy, aralkyl or aralkyloxy,but wherein, in the case where R represents cyano and X simultaneously represents an azido group, Ar does not represent unsubstituted phenyl and does not represent 5-nitro-2-pyridyl. The compounds exhibit herbicidal and plant growth-regulating activity.Type: GrantFiled: December 16, 1986Date of Patent: September 13, 1988Assignee: Bayer AktiengesellschaftInventors: Reinhold Gehring, Markus Lindig, Otto Schallner, Jorg Stetter, Hans-Joachim Santel, Robert R. Schmidt, Klaus Lurssen
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Patent number: 4767771Abstract: Novel fungicidal pyridyl imidates having the general structural formula ##STR1## wherein R is selected from the group consisting of C.sub.1 -C.sub.16 alkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.2 14 C.sub.8 alkenyl, C.sub.2 -C.sub.8 substituted alkenyl, C.sub.3 -C.sub.4 carboalkoxyalkyl, aryl, arylalkyl having C.sub.1 -C.sub.3 alkyl, substituted aryl and arylalkyl wherein the substituents are --Cl, --Br, --F and --NO.sub.2, furfuryl pyridyl, C.sub.1 -C.sub.6 alkyl substituted phosphorus, and ##STR2## wherein R.sub.3 and R.sub.4 are C.sub.1 -C.sub.10 alkyl and can form a heterocyclic ring, R.sub.1 is selected from the group consisting of halogen, C.sub.1 -C.sub.3 alkoxy and C.sub.1 -C.sub.3 haloalkoxy, R.sub.2 is selected from the group consisting of methyl and hydrogen, and X is S or O; and fungicidally accepable organic and inorganic salts thereof.Type: GrantFiled: April 15, 1987Date of Patent: August 30, 1988Assignee: Stauffer Chemical Co.Inventors: Don R. Baker, Keith H. Brownell
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Patent number: 4756739Abstract: The compounds of the formula I ##STR1## in which A denotes N or N.fwdarw.O, Z denotes O or NH, R denotes H, (halo)alkyl, (halo)alkenyl, (halo)alkynyl or alkoxycarbonyl, R.sup.1 denotes hydrogen, halogen, amino, --NHOH, hydroxyl, (substituted) phenylazo or a radical of the formulae Y=C=N--, Y.sup.1 Y.sup.2 C.dbd.N--, Y.sup.3 NH-- or ##STR2## K denotes 0 or 1, and m and n, independently of one another, denote a number from 1 to 4, with the proviso that, when Z-R denotes OH or NH.sub.2, (R.sup.1).sub.n denotes at least one radical of the formula ##STR3## or represents two radicals, in the 5 or 6 position of the heterocyclic ring, which, in the 5 position, denote halogen and, in the 6 position, denote a radical of the group comprising halogen, amino, hydroxyl or phenylazo, which may be substituted as specified above, are valuable intermediates in the synthesis of plant protection agents.Type: GrantFiled: December 19, 1986Date of Patent: July 12, 1988Assignee: Hoechst AktiengesellschaftInventors: Andreas Fuss, Volker Koch
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Patent number: 4755209Abstract: A phenoxyalkanoylaminomethylphosphonic acid represented by the following formula (I) ##STR1## wherein X and Y are identical or different and each represents a hydrogen atom, a halogen atom, CF.sub.3 or an alkyl group having not more than 5 carbon atoms, Z represents CH or N, and R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are identical or different and each represents a hydrogen atom or a lower alkyl group having 1 to 5 carbon atoms. The compound is useful, as a herbicide, for eradicating weeds, especially narrow-leaved weeds.Type: GrantFiled: April 4, 1986Date of Patent: July 5, 1988Assignee: Teijin LimitedInventors: Shizuo Azuma, Toshiyuki Hiramatsu, Koji Nakagawa, Yataro Ichikawa
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Patent number: 4746653Abstract: The present invention is concerned with the phosphonic acids of formula I ##STR1## wherein one or both of the acidic hydroxy groups of the phosphonic acid moiety may be functionalized in form of pharmaceutically acceptable mono- or di-esters; wherein Y represents optionally substituted 2-carboxypyrrolidinyl, 2-carboxy-2,5-dihydropyrrolyl, 2-carboxy-1,2,3,6-tetrahydropyridinyl, 2-carboxy-1,2,5,6-tetrahydropyridinyl, 2-carboxypiperidinyl, 2-carboxytetrahydroquinolinyl or 2-carboxyperhydroquinolinyl, 2-carboxy-2,3-dihydroindolyl, 2-carboxyperhydroindolyl, and in each of which the carboxy group may be functionalized in form of a pharmaceutically acceptable ester or amide; A represents B--X--D wherein B represents a direct bond, or straight chain or branched lower alkylene; X represents O, S, SO, SO.sub.2, CO--NR.sub.b, R.sub.b N--CO or N--Ra; Ra represents hydrogen, lower alkyl, aryl, aryl-lower alkyl or acyl; R.sub.Type: GrantFiled: February 28, 1986Date of Patent: May 24, 1988Assignee: Ciba-Geigy CorporationInventors: Alan J. Hutchison, Kenneth R. Shaw, Josef A. Schneider