Nitrogen In Alcohol Moiety Other Than As Nitro, Nitroso Or Isocyanate Patents (Class 560/250)
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Patent number: 4921524Abstract: The invention provides compounds of the general formula ##STR1## wherein R represents a hydrogen atom, or an optionally substituted alkyl or acyl group, or an alkenyl or alkynyl group or an inorganic or organic cation;R.sup.1 represents an alkyl, haloalkyl, alkenyl, alkynyl or phenyl group;R.sup.2 represents an optionally substituted alkyl or phenalkyl group or a cycloalkyl, alkenyl, haloalkenyl, alkynyl or haloalkynyl group;R.sup.3 represents a hydrogen atom or an alkyl group; andone of R.sub.4 and R.sup.5 represents a hydrogen atom or an alkyl group, while the other of R.sup.4 and R.sup.5 represents an optionally substituted phenyl group; together with their use as herbicides and their preparation using novel intermediates.Type: GrantFiled: April 14, 1988Date of Patent: May 1, 1990Assignee: Shell Internationale Research Maatschappij B.V.Inventors: Terence Gilkerson, Robert W. Shaw, David C. Jennens
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Patent number: 4918236Abstract: A compound of the formula ##STR1## wherein R is halogen, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, nitro; cyano; C.sub.1 -C.sub.2 haloalkyl, or R.sup.a SO.sub.m -wherein m is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl; R.sup.1 is hydrogen or C.sub.1 -C.sub.2 alkyl; R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.1 and R.sup.2 together are alkylene having 2 to 5 carbon atoms; R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.3 and R.sup.4 together are oxo; R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.6 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.5 and R.sup.6 together are alkylene having 2 to 5 carbon atoms; R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 - C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n -wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.Type: GrantFiled: June 9, 1986Date of Patent: April 17, 1990Assignee: ICI Americas Inc.Inventors: Christopher G. Knudsen, William J. Michaely
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Patent number: 4916156Abstract: The present invention relates to aromatic derivatives of the formula: ##STR1## in which: n represents an integer between 2 and 10;R.sub.1 and R.sub.2 are identical or different and represent a cycloalkyl containing 3 to 6 carbon atoms or an alkyl containing from 1 to 6 carbon atoms which is unsubstituted or substituted by a phenyl or benzyl group; orR.sub.1 and R.sub.2, together with the nitrogen atom to which they are bonded, form a heterocycle selected from pyrrolidin-1-yl, piperidino, azepin-1-yl, hexamethyleneimino, 4-methylpiperidino, 4-benzylpiperidino, 4-phenylpiperidino, 1,2,3,4-tetrahydroisoquinol-2-yl, morpholino and imidazol-1-yl groups;R.sub.3 represents a hydrogen, a halogen, a methyl or a phenyl;R.sub.4 represents a hydrogen, a halogen or a methyl; or R.sub.3 and R.sub.4, taken together with the benzene ring to which they are bonded, form a naphth-1-yl or naphth-2-yl group;Y represents a direct bond, a methyleneoxy group, a methylenethio group or a vinylene group; andR.sub.Type: GrantFiled: April 6, 1988Date of Patent: April 10, 1990Assignee: SanofiInventors: Madeleine Mosse, Vincenzo Proietto
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Patent number: 4882429Abstract: Azetidinones represented by the formula ##STR1## are prepared by a multistep process from L-(-)-theonine via an epoxyamide.Type: GrantFiled: March 3, 1986Date of Patent: November 21, 1989Assignee: Schering CorporationInventors: Stuart W. McCombie, Michael P. Kirkup, Amy Sommese Boland
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Patent number: 4882329Abstract: Calcium antagonists of the formula ##STR1## with R(1), R(2), R(3) and R(4) being, inter alia, H, alkyl, alkoxy, halogen, in some cases phenyl; m being 1-4; n being 0-3; X being CH.sub.2, O, S, CO, CHOH or CR.sub.2, and R(5) being various groups containing nitrogen atoms, are described.They are obtained by reaction of compounds II which are likewise new and which contain in place of R(5) a leaving group Y (Cl, Br, I) with the appropriate (cyclic) amino compound.Another synthesis comprises reaction of the appropriate indolinone derivative IV which has a non-etherified hydroxyl group with a side chain which contains a terminal leaving group Z (Cl, Br, I) in the presence of a base.Furthermore, indolinone derivatives VI with an ether side chain with a terminal epoxide group can be reacted with (cyclic) amines to give compounds I.Type: GrantFiled: January 30, 1989Date of Patent: November 21, 1989Assignee: Hoechst AktiengesellschaftInventors: Ulrich Lerch, Rainer Henning, Joachim Kaiser
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Patent number: 4880839Abstract: An acylanilide of the formula: ##STR1## wherein R.sup.1 or R.sup.2 which may be the same or different, each is an electron-withdrawing substituent, alkylthio or phenylthio or R.sup.1 is hydrogen, alkyl or alkoxy; wherein R.sup.3 is hydrogen or halogen; wherein R.sup.4 is hydrogen or acyl wherein A is branched-chain alkylene; and wherein R.sup.5 is phenyl, substituted phenyl or naphthyl. The compounds possess progestational activity.Type: GrantFiled: June 16, 1987Date of Patent: November 14, 1989Assignee: Imperial Chemical Industries PLCInventor: Howard Tucker
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Patent number: 4877824Abstract: Compounds of the formula (I) ##STR1## in which the Rs independently of one another are H, phenyl, naphthyl or C.sub.7 -C.sub.30 alkaryl and R.sup.1 is H, C.sub.1 -C.sub.8 alkyl, C.sub.7 -C.sub.9 aralkyl, C.sub.5 -C.sub.12 cycloalkyl, phenyl, naphthyl, C.sub.7 -C.sub.30 alkaryl or a group of the formula (II)--(CH.sub.2).sub.a --SR.sup.3 (II)R.sup.2 is C.sub.7 -C.sub.30 alkaryl, phenyl, naphthyl or phenyl containing, in the para-position, an HO or C.sub.1 -C.sub.18 alkoxy group or a group of the formulae ##STR2## or R.sup.1 and R.sup.2, together with the nitrogen atom to which they are attached, are a radical of the formula (III) ##STR3## R.sup.3 is a radical of the formulae --(CH.sub.2).sub.b --COOR.sup.6 or --(CH.sub.2).sub.2 OCOR.sup.7, a is the number 1, 2 or 3 and b is the number 1 or 2, and R.sup.4 is phenyl or a group of the formula (II), the two R.sup.5 s independently of one another are H, C.sub.1 -C.sub.24 alkyl, C.sub.5 -C.sub.12 cycloalkyl or C.sub.7 -C.sub.9 aralkyl, and R.sup.6 is H, C.sub.1 -C.Type: GrantFiled: January 25, 1989Date of Patent: October 31, 1989Assignee: Ciba-Geigy CorporationInventor: Samuel Evans
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Patent number: 4874554Abstract: Quaternary ammonium compounds corresponding to the formula ##STR1## are produced by esterification of ether amines corresponding to the formula ##STR2## with a fatty acid of the formula R.sup.2 --COOH and quaternization of the product obtained with an alkyl halide or a dialkyl sulfate. They are suitable for use as conditioning and revitalizing agents in hair-cosmetic preparations.Type: GrantFiled: July 10, 1987Date of Patent: October 17, 1989Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Fritz Lange, Peter Busch, Klaus Thiele
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Patent number: 4861916Abstract: Compounds of the general formula I ##STR1## wherein Z is CR.sup.1 R.sup.2 (OR.sup.3) or phenyl,R.sup.1 being H, C.sub.1-6 -alkyl or phenyl,R.sup.2 being H, C.sub.1-6 -alkyl or C.sub.1-6 -alkoxy andR.sup.3 being H, C.sub.1-6 -alkyl or C.sub.1-6 -alkanoyl andZ' is Y--[(CH.sub.2).sub.m --X].sub.n --,X being CH.sub.2 or 0,Y being OH; COOH or SO.sub.3 H including the alkali metal, alkaline earth metal or ammonium salts thereof and also the salts thereof with organic nitrogen bases; or NRR' in which R and R' are in each case H, C.sub.1-20 -alkyl or C.sub.1-4 -hydroxyalkyl, if appropriate quaternized or in the form of the acid addition salts, andn and m each being the numbers 1-4,are excellently suitable as photoinitiators for the photopolymerization of ethylenically unsaturated compounds, in particular in aqueous systems.Type: GrantFiled: December 3, 1986Date of Patent: August 29, 1989Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Manfred Kohler, Jorg Ohngemach, Gregor Wehner, Jurgen Gehlhaus
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Patent number: 4855489Abstract: The present invention covers a novel series of 2-acyloxypropylamine derivatives, processes for preparing them, compositions containing them, and methods for using them. The compounds are active in the inhibition of protein kinase C and thrombocyto aggregation stimulated by diacylglycerols.Type: GrantFiled: July 15, 1987Date of Patent: August 8, 1989Assignee: Goedecke AktiengesellschaftInventors: Uwe Trostmann, Christoph Schachtele, Karl Mannhardt, Claus Rudolph, Dieter Marme
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Patent number: 4835179Abstract: Dihydrodibenzocycloheptyliden-ethylene derivatives of the general formula: ##STR1## in which, R.sub.1 represents an alkyl group having from 1 to 4 carbon atoms;R.sub.2 represents a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms; andR.sub.3 represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms or --CO--(C.sub.1 -C.sub.4 alkyl),are disclosed. These compounds are useful in the treatment of ulcer conditions.Type: GrantFiled: May 26, 1987Date of Patent: May 30, 1989Assignee: Sociedad Espanola de Especialidades Farmacotera peuticasInventors: Xavier D. Cirera, Romeo R. Andreoli, Pedro P. Lloveras, Leonida Bruseghini, Jose P. Irurre
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Patent number: 4822902Abstract: Certain N-acetonylbenzamides exhibit low toxicity to plants are particularly useful for control of fungi, especially Phycomycetes.Type: GrantFiled: July 26, 1984Date of Patent: April 18, 1989Assignee: Rohm and Haas CompanyInventors: H. Edwin Carley, Ashok K. Sharma
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Patent number: 4816604Abstract: The compounds of formula I, ##STR1## where the substituents have various significances, and physiologically acceptable hydrolyzable derivatives thereof having the hydroxy group in the 2 position of the 3-aminopropoxy side chain in esterifield form, are useful as cardioselective .beta.-adrenoceptor blocking agents.Type: GrantFiled: March 9, 1987Date of Patent: March 28, 1989Assignee: William J. LouisInventors: William J. Louis, Richard Berthold, Andre Stoll
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Patent number: 4808572Abstract: Novel asymmetric thioethers of the formula ##STR1## in which the general symbols have the following meanings: a is an integer of from 1 to 7,R.sup.o represents hydrogen or C.sub.1-7 -alkanoyl,R.sup.1 represents C.sub.1-3 -alkyl which may be substituted at the terminal carbon atom by a free or acylated hydroxy group, by a halogen atom having an atomic number of at most 17, or by methoxy, or represents C.sub.1-3 -perfluoroalkyl,R.sup.2 represents an optionally unsaturated aliphatic radical having from 5 to 15 carbon atoms,A represents ethylene or alternatively, if R.sup.1 represents a halogenated radical and/or B represents phenylene or ethylene, a single bond or vinylene,B represents a single bond, ethynylene or phenylene,R.sup.3 represents hydroxy, C.sub.Type: GrantFiled: December 1, 1986Date of Patent: February 28, 1989Assignee: Ciba-Geigy CorporationInventors: Andreas Beck, Werner Breitenstein, Andreas von Sprecher, Robert W. Lang, Konrad Oertle
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Patent number: 4785004Abstract: Novel asymmetric thioethers of the formula ##STR1## in which the general symbols have the following meanings: R.sup.0 represents hydrogen or C.sub.1-7 -alkanoyl,R.sup.1 represents C.sub.1-3 -alkyl which may be substituted by one or more halogen atoms having an atomic number of at most 17,R.sup.2 represents an aliphatic radical having from 5 to 15 carbon atoms,A represents ethylene, a single bond or vinylene,B.sup.1 represents C.sub.1-7 -alkylene or phenylene,B.sup.2 represents a single bond, ethylene or phenylene, andM represents an aromatic radical of the partial formula ##STR2## in which the symbols have the following meanings: R.sup.3 represents hydrogen or C.sub.1-4 -alkyl,X represents NH, O, S or if R.sup.4 represents hydrogen, a single bond,one of the symbols R.sup.4 and R.sup.5 represents hydrogen and the other represents the group --CO--R.sup.6, orR.sup.4 and R.sup.5 together represent the radical --CO--C(R.sup.6).dbd.C(R.sup.7)--or--CO--C(R.sup.7).dbd.C(R.sup.6)--orR.sup.4 R.sup.Type: GrantFiled: December 15, 1986Date of Patent: November 15, 1988Assignee: Ciba-Geigy CorporationInventors: Andreas Von Sprecher, Werner Breitenstein, Andreas Beck, Robert W. Lang, Konrad Oertle
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Patent number: 4767447Abstract: Compounds of the formula ##STR1## wherein R is halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; trifluoromethoxy or difluoromethoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl, trifluoromethyl or difluoromethyl;R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.1 and R.sup.2 together are C.sub.2 -C.sub.5 alkylene;R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.3 and R.sup.4 together are C.sub.2 -C.sub.5 alkylene;R.sup.5, R.sup.6, R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n -- wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.Type: GrantFiled: September 12, 1986Date of Patent: August 30, 1988Assignee: Stauffer Chemical CompanyInventors: David L. Lee, William J. Michaely
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Patent number: 4761502Abstract: Polyalkyleneoxytrifluoromethylaniline compounds are provided of the formula: ##STR1## wherein R.sub.1 is independently selected from H, a lower alkyl group containing from 1 to about 10 carbon atoms, CH.sub.2 Cl, CH.sub.2 Br, CH.sub.2 OH, phenyl or ##STR2## where R.sub.5 is H or a lower alkyl group containing from 1 to about 9 carbon atoms; R.sub.2 is selected from H, a lower alkyl group containing from 1 to about 9 carbon atoms, alkylaryl containing from 7 to about 11 carbon atoms, cyanoalkyl, or acyl; R.sub.3 is selected from a lower alkyl group containing from 1 to about 9 carbon atoms, cyanoalkyl, acetoxyalkyl or ##STR3## wherein R.sub.1 and R.sub.2 are as given above; R.sub.4 is H, CF.sub.3, a lower alkyl group containing from 1 to about 9 carbon atoms, Cl or Br and n is 0 or an integer from 1 to about 125.Type: GrantFiled: September 8, 1986Date of Patent: August 2, 1988Assignee: Milliken Research CorporationInventors: Edward W. Kluger, Patrick D. Moore, Joe T. Burchette
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Patent number: 4740595Abstract: A multistep process is disclosed for preparing azetidinone intermediates used in the making penems and carbapenems wherein intermediates containing ##STR1## R' is independently hydrogen or 1, 2 or 3 of lower alkyl or lower alkoxy, preferably hydrogen, wherein R" is methyl, ethyl, a phenyl or alkyl, preferably ethyl, as a readily removable nitrogen protecting group are made.Type: GrantFiled: March 13, 1986Date of Patent: April 26, 1988Assignee: Schering CorporationInventor: Samuel Chackalamannil
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Patent number: 4727151Abstract: Labile quaternary ammonium salts of the following formula (I) and (II) are provided: ##STR1## wherein N represents a tertiary aliphatic amine; wherein N represents an unsaturated amine; wherein R represents a member selected from the group consisting of a hydrogen atom, a C.sub.1 -C.sub.8 open chain or cyclo alkyl group, a C.sub.1 -C.sub.8 alkoxyalkyl group, a C.sub.1 -C.sub.8 acyloxyalkyl group, a C.sub.1 -C.sub.8 haloalkyl group, a C.sub.1 -C.sub.8 carboxyalkyl group, a C.sub.2 -C.sub.8 alkenylphenyl group, an aryl group, and a substituted aryl group, whose substituents are selected from the group consisting of a halogen atom, an O-lower alkyl (C.sub.1 -C.sub.4) group, an O-acyl group, a nitro group, a carboxyl group, and a carboethoxy group; wherein R.sub.1 which may be the same or different, represents any member defined by R above with the proviso that R.sub.Type: GrantFiled: November 22, 1978Date of Patent: February 23, 1988Assignee: INTERx Research CorporationInventor: Nicolae S. Bodor
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Patent number: 4686309Abstract: The invention provides compounds of formula: ##STR1## in which R=H, halogen, alkyl, alkyloxy, alkythio, NH.sub.2, alkylamino, dialkylamino or CF.sub.3, R.sub.3 =H or alkyl, either R.sub.4 and R.sub.5 =H and R.sub.1 and R.sub.2 =H or alkyl, optionally substituted by alkenyl (2 to 4 C) or alternatively R.sub.1 and R.sub.2 form together a saturated heterocyclic ring containing 4 to 7 ring members and optionally containing another heteroatom such as O, S or N optionally substituted by alkyl, or R.sub.4 =H, R.sub.1 =H or alkyl and R.sub.2 and R.sub.5 together form an alkylene (3 to 4 C) radical and (i) either A=alkyl or phenyl which is unsubstituted or substituted by one or two substituents chosen from halogen, alkyl, alkyloxy, alkylthio, NH.sub.2, alkylamino, dialkylamino, NO.sub.2 or CF.sub.3 or alternatively A=pyridyl, benzyl or cycloalkyl (3 to 6C), Y=S, SO or SO.sub.2 or a radical: ##STR2## in which R.sub.6 =H or alkyl and R.sub.Type: GrantFiled: February 15, 1985Date of Patent: August 11, 1987Assignee: Rhone-Poulenc SanteInventors: Jean-Claude Barriere, Jean-Pierre Corbet, Claude Cotrel, Daniel Farge, Jean-Marc Paris
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Patent number: 4678855Abstract: Benzenesulfonamides with a substituted-alkyl-S(O).sub.n -substituent are carbonic anhydrase inhibitors useful in the treatment of elevated intraocular pressure.Type: GrantFiled: October 9, 1985Date of Patent: July 7, 1987Assignee: Merck & Co., Inc.Inventor: Kenneth L. Shepard
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Patent number: 4652584Abstract: Phenoxypropanol derivatives having a 2-acetylenic moiety on the phenyl group thereof of the following formula (I): ##STR1## and their use as anti-hypertensives, e.g. in man. Also part of the invention are pharmaceutical compositions and intermediates used in the synthesis.Type: GrantFiled: July 13, 1984Date of Patent: March 24, 1987Assignee: McNeilab, Inc.Inventor: John R. Carson
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Patent number: 4652303Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: W are selected from the group consisting of:the groups R.sup.5 --CO-- and R.sup.5 --CS-- wherein: R.sup.5 is selected from alkenyl, alkynyl, benzyl, phenyl, substituted alkyl, substituted alkenyl, substituted alkynyl, substituted benzyl, substituted phenyl and the acetal, hemiacetal, oxime, imine and Schiff base derivatives of the group R.sup.5 --CO--;the groups Y--CO-- and Y--CS-- wherein Y is selected from hydroxy, mercapto, alkylthio and the groups MO-- and MS-- wherein M is an organic or an inorganic cation;the groups R.sup.6 R.sup.7 NCO-- and R.sup.6 R.sup.7 NCS-- wherein R.sup.6 and R.sup.7 are independently selected from hydrogen, alkyl, substituted alkyl, alkanoyl, carboxy, alkoxycarbonyl, alkylsulfonyl, benzoyl, benzenesulfonyl, substituted benzoyl, substituted benzenesulfonyl, or R.sup.6 and R.sup.Type: GrantFiled: July 2, 1984Date of Patent: March 24, 1987Assignee: ICI Australia LimitedInventors: Keith G. Watson, Graham J. Bird, Graeme J. Farquharson
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Patent number: 4640708Abstract: Compounds of the formula ##STR1## wherein: R.sup.5 is a bicyclic aryl or nitrogen-containing heteroaryl ring system such as naphthyl, quinolyl, isoquinolyl or tetrahydroisoquinolyl, optionally substituted by a wide variety of groups;R.sup.4 and R.sup.1 are preferably hydrogen but may be other groups andR.sup.2 and R.sup.3 are selected from alkyl, haloalkyl, alkenyl, haloalkenyl and alkynyl, show high general grass-killing activity with good selectivity to many broad-leaf crops and in some instances selectivity to small-grain cereals. Processes for the preparation of compounds of formula I, intermediates in the preparation of compounds I and the herbicidal properties of compounds I are described.Type: GrantFiled: March 20, 1984Date of Patent: February 3, 1987Assignee: ICI Australia LimitedInventors: Graham J. Bird, Graeme J. Farquharson, Keith G. Watson
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Patent number: 4636505Abstract: Acylanilides of the formula ##STR1## wherein R.sup.1 and R.sup.2, the same or different, each is cyano, carbamoyl, nitro, halogeno, perfluoroalkyl or other defined substituents;R.sup.3 is hydrogen or halogen;R.sup.4 is hydrogen or alkyl, or is joined to R.sup.5 ;R.sup.5 is hydrogen, hydroxy, alkoxy or acyloxy or is joined to R.sup.4 ;R.sup.6 is alkyl or halogenoalkyl, or has the formula --A.sup.3 --R.sup.8 or --A.sup.4 --X.sup.2 --A.sup.5 --R.sup.9 ;A.sup.1 and A.sup.4, the same or different, each is alkylene;A.sup.2, A.sup.3 and A.sup.5, the same or different, each is a direct link or alkylene;X.sup.1 and X.sup.2, the same or different, each is oxygen, sulphur, sulphinyl, sulphonyl, imino or alkylimino;R.sup.7 and R.sup.9, the same or different, each is alkyl, alkenyl, hydroxyalkyl, cycloalkyl, phenyl optionally substituted, naphthyl or heterocyclic optionally substituted;and R.sup.8 is phenyl, naphthyl or heterocyclic as defined above for R.sup.7 or R.sup.Type: GrantFiled: July 15, 1983Date of Patent: January 13, 1987Assignee: Imperial Chemical Industries PLCInventor: Howard Tucker
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Patent number: 4629736Abstract: Fatty acid derivatives represented by the general formula ##STR1## and salts thereof. The compounds of this invention have excellent fibrinolytic action and a highly improved solubility.Type: GrantFiled: September 28, 1984Date of Patent: December 16, 1986Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Shin-ichi Tsukamoto, Yoshinobu Nagano, Kimio Katsuda
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Patent number: 4629727Abstract: Compounds of formula I ##STR1## in which n=0 or 1; in which, when n=0, R.sub.1 is H, an alkyl, a cycloalkyl, a cycloalkylmethyl, an alkenyl or, an alkynyl group a heterocyclic ring or an optionally substituted phenyl ring or when n=1, R.sub.1 is H or an alkyl group;in which R.sub.2 and R.sub.3 are H or an alkyl group;in which A is a group of formula III--(CH.sub.2).sub.x --W--(CH.sub.2).sub.y -- IIIin which W is an oxygen atom or a group of formula --S(O).sub.m --, a group of formula --CR.sub.12 R.sub.13 --, a cycloalkylidene group or a cycloalkylene group; x is 0 or an integer from 1 to 5; y is 0 or an integer from 1 to 5.in which R.sub.4 is a carbocyclic ring, a heterocyclic ring, a cyano group, a carbamoyl group, an alkoxycarbonyl group, an amido group, an acyloxy group, a hydroxy group, a thiol group, or a group of formula --OR.sub.20, --SR.sub.20, --SOR.sub.20 or SO.sub.2 R.sub.20.in which R.sub.5, R.sub.6 and R.sub.Type: GrantFiled: September 28, 1983Date of Patent: December 16, 1986Assignee: The Boots Company PLCInventors: Antonin Kozlik, Wilfred H. Wells
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Patent number: 4613619Abstract: The invention concerns novel anti-arrhythmic amino-alcohol derivatives, characterized by the general formula (1) ##STR1## or pharmaceutically acceptable salts thereof, wherein R.sub.1, R.sub.2 and R.sub.3 each independently represent hydrogen, alkyl having 1-6 carbon atoms, alkoxy having 1-6 carbon atoms, acyloxy having 1-6 carbon atoms, hydroxy, halogen or optionally alkyl-substituted amino;R.sub.4 represents hydrogen, hydroxy or alkyl having 1-6 carbon atoms,R.sub.5 represents hydrogen or alkyl having 1-6 carbon atoms,R.sub.6 represents hydrogen, acyl having 1-18 carbon atoms or alkyl having 1-6 carbon atoms,R.sub.7 and R.sub.8 each independently represent hydrogen or alkyl having 1-6 carbon atoms,X represents a direct bond or an oxygen atom, andn and m each independently are integers having a value of 1 or 2, whereby the sum of n and m is 2 or 3.Type: GrantFiled: February 22, 1985Date of Patent: September 23, 1986Assignee: AKZO N.V.Inventors: Thomas Sleigh, David S. Savage, John K. Clark
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Patent number: 4609673Abstract: The present invention provides carboxylic acid derivatives of the general formula: ##STR1## wherein R is a hydrogen atom, alkyl, a metal cation or an ammonium or alkylammonium ion, R.sub.1 is a hydrogen atom, a hydroxyl group or an alkyl, O-alkyl,O-benzyl or O-acyl radical, R.sub.2 is a hydrogen atom or an alkyl, aryl or aralkyl radical, n is 0, 1 or 2 and R.sub.Type: GrantFiled: December 18, 1984Date of Patent: September 2, 1986Assignee: Boehringer Mannheim GmbHInventors: Hermann Eggerer, Bernd Hagenbruch, Tran G. Nguyen, Karlheinz Stegmeier, Johannes Pill
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Patent number: 4600797Abstract: Process for the preparation of a nitroaminobenzene by nitrating an aminobenzene which is protected at the nitrogen wherein the nitration is carried out by the simultaneous combination of nitric acid and the aminobenzene to be nitrated, in the presence of inert solvents such as methylene chloride.Type: GrantFiled: February 18, 1983Date of Patent: July 15, 1986Assignee: Bayer AktiengesellschaftInventor: Willi Schossler
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Patent number: 4587361Abstract: Flukicidal N-[4-(1-phenylethenyl)phenyl]-2-hydroxy-3,5-dihalobenzamides are prepared by reacting a halosalicylic acid with a 1-(4-aminophenyl)-1-phenylethylene in the presence of a halo condensing agent. A species of the invention is N-[4-(1-phenylethenyl)phenyl]-2-hydroxy-3,5-diiodobenzamide.Type: GrantFiled: May 7, 1984Date of Patent: May 6, 1986Assignee: SmithKline Beckman CorporationInventors: Alfred W. Chow, Vassilios J. Theodorides
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Patent number: 4556737Abstract: This invention provides novel sulfonium compounds, processes for the preparation of the sulfonium compounds, and pharmacological composition containing the sulfonium compound. The compounds of this invention are useful for treating allergy.Type: GrantFiled: February 27, 1984Date of Patent: December 3, 1985Assignee: Taiho Pharmaceutical Company LimitedInventors: Akihide Koda, Mikio Hori, Naosuke Matsuura, Mitsugi Yasumoto, Ichiro Yamawaki, Shuichi Ueda, Yukio Tada
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Patent number: 4535186Abstract: This invention provides a group of hydroxycycloalkanephenethyl amine antidepressant derivatives of the following structural formula: ##STR1## in which A is a moiety of the formula ##STR2## where the dotted line represents optional unsaturation;R.sub.1 is hydrogen or alkyl;R.sub.2 is alkyl;R.sub.4 is hydrogen, alkyl, formyl or alkanoyl;R.sub.5 and R.sub.6 are, independently, hydrogen, hydroxyl, alkyl, alkoxy, alkanoyloxy, cyano, nitro, alkylmercapto, amino, alkylamino, dialkylamino, alkanamido, halo, trifluoromethyl or, taken together, methylenedioxy;R.sub.7 is hydrogen or alkyl; andn is 0, 1, 2, 3 or 4;or a pharmaceutically acceptable salt thereof.Type: GrantFiled: October 26, 1983Date of Patent: August 13, 1985Assignee: American Home Products CorporationInventors: G. E. Morris Husbands, John P. Yardley, Eric A. Muth
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Patent number: 4529813Abstract: Insecticidally active vinyl-cyclopropane carboxylic acid esters of the formula ##STR1## are prepared by reacting ##STR2## in which R.sup.12 is a radical selected from the group consisting of ##STR3## with an alcoholate of the formulaM--O--R.sup.8.Various processes for making the intermediates are also described. Many of the intermediates and end products are new.Type: GrantFiled: March 14, 1980Date of Patent: July 16, 1985Assignee: Bayer AktiengesellschaftInventors: Hans-Georg Heine, Willy Hartmann
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Patent number: 4518789Abstract: Therapeutic as well as preventive measures to alleviate the symptoms of dermatologic and other conditions and disorders with phenyl alpha-acyloxyacetamide derivatives is disclosed. Dermatologic and other conditions and disorders in humans in which the compounds may be useful include pruritus, atopic dermatitis, eczema, psoriasis, acne, dry skin, dandruff, malodors of integumental areas; and various aches, pains and discomforts of skin, joints and other body parts. The phenyl alpha-acyloxyacetamide derivatives include, for example, N-ethyl phenyl alpha-acetoxyacetamide, N-benzyl phenyl-alpha-acetoxyacetamide, N-phenethyl phenyl-alpha-acetoxyacetamide, N-benzyl diphenyl-alpha-acetoxyacetamide and N-phenethyl diphenyl-alpha-acetoxyacetamide. The compositions containing the active ingredients are also useful for treatment of skin conditions or disorders, and musculoskeletal disorders, of domestic animals, for example dogs, such as dry skin, scurf, eczema, mange, prurigo, malodors, arthritis or myositis.Type: GrantFiled: May 17, 1983Date of Patent: May 21, 1985Inventors: Ruey J. Yu, Eugene J. Van Scott
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Patent number: 4474977Abstract: The new amino-alcohol derivatives according to the invention have the formula: ##STR1## wherein: (a) R.sub.1 is hydrogen, an alkylthio C.sub.1 -C.sub.5 radical, a cycloalkylthio C.sub.5 -C.sub.6 radical, an alkoxy C.sub.1 -C.sub.5 radical, a cycloalkyloxy C.sub.5 -C.sub.6 radical, an alkyl C.sub.1 -C.sub.5 radical, a cycloalkyl C.sub.5 -C.sub.6 radical or a halogen atom;(b) R.sub.2 is a lower alkyl C.sub.1 -C.sub.3 radical;(c) R.sub.3 is an alkyl C.sub.1 -C.sub.18 radical, substituted or not, an alkenyl C.sub.6 -C.sub.18 radical substituted or not, a cycloalkyl C.sub.5 -C.sub.9 radical;(d) R.sub.4 is an acyl group having the formula: ##STR2## in which R.sub.5 represents an alkyl C.sub.1 -C.sub.10 substituted or not, an alkenyl C.sub.2 -C.sub.4, a cycloalkyl C.sub.3 -C.sub.8, a phenyl substituted or not or a cinnamyl radical, R.sub.4 being hydrogen if R.sub.1 is hydrogen, an alkyl, alkoxy, cycloalkoxy or cycloalkyl radical or a halogen atom.Type: GrantFiled: April 28, 1978Date of Patent: October 2, 1984Assignee: Continental Pharma S.A.Inventors: Georges Lambelin, Romeo Roncucci, Joseph Roba, Claude Gillet, Michel Snyers
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Patent number: 4460600Abstract: Cis- and trans-N-[2-amino(adjacenty substituted bis(alkyloxy), bis(alkylthio), alkylthio or mercapto group substituted)-cycloaliphatic]benzeneacetamide and -benzamide compounds, e.g., (.+-.)-(1.alpha.,2.beta.)-4-bromo-N-[3,3-dimethoxy-2-(1-pyrrolidinyl)cyclo hexyl]-N-methylbenzamide, and salts thereof, are provided. These compounds have analgesic properties. Processes for their preparation are disclosed. Pharmaceutical compositions and methods of use are also provided.Type: GrantFiled: November 4, 1982Date of Patent: July 17, 1984Assignee: The Upjohn CompanyInventors: Lester J. Kaplan, Moses W. McMillan, Jacob Szmuszkovicz
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Patent number: 4448773Abstract: Compounds of the formula ##STR1## in which Ar is 2-alkyl-, -alkoxy- or -halo-methyl-phenyl or .alpha.-naphthyl, each of which is further substituted,R.sub.1 is 2-furyl, 2-tetrahydrofuryl, alkenyl, cyclopropyl, .beta.-alkoxyethyl, hydroxymethyl, triazolylmethyl, imidazolylmethyl, pyrazolylmethyl, alkylsulfinyl, alkylsulfonyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, alkylsulfinyloxy, dialkylaminosulfinyloxy, phosphoric or thiophosphoric esters or amides, or alkylcarbonyloxy,R.sub.7 is hydrogen or optionally-substituted methyl or ethyl, andR.sub.8 is alkyl optionally substituted by alkoxy,are microbicidally, in particular fungicidally, active. Preferred compounds are those in which Ar is 2-methylphenyl, 2-methoxyphenyl, 2-chlorophenyl or .alpha.-naphthyl, each of which is further substituted by azido, and each of R.sub.7 and R.sub.8 is methyl.Type: GrantFiled: April 22, 1982Date of Patent: May 15, 1984Assignee: Ciba-Geigy CorporationInventors: Peter Riebli, Hanspeter Fischer, Rudolph C. Thummel, Adolf Hubele
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Patent number: 4440566Abstract: Substituted 2-[1-(oxyamino)alkylidene]-cyclohexane-1,3-diones have herbicidal activity against grassy weeds.Type: GrantFiled: August 9, 1982Date of Patent: April 3, 1984Assignee: Chevron Research CompanyInventor: Tatao Luo
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Patent number: 4430114Abstract: The invention is preemergence herbicidal methods employing novel dinitroanilines for control of certain grasses and broadleaf weeds in the presence of graminaceous crops, especially rice.Type: GrantFiled: May 4, 1981Date of Patent: February 7, 1984Assignee: American Cyanamid CompanyInventors: Albert W. Lutz, Robert E. Diehl
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Patent number: 4429152Abstract: The 3-substituted 2,4,6-trihalogenated benzamides having the formula I ##STR1## wherein Hal is chlorine, bromine, or iodine andZ is a carboxyl group or the group ##STR2## wherein P is 1 and L is 0 or 1, with the proviso that L is 0 when K is 0; K is 0, 2, 3, or 4;M is 0, 1, 2 or 3;N is 0 or 1;X is a hydrogen atom;Y is a hydrogen atom or a lower alkyl group of 1-4 carbon atoms, or when either M or N is other than 0, a hydroxy group, a C.sub.1-6 alkoxy group or a C.sub.1-4 acyloxy group, or when N is 1 and M is other than 0, X and Y together represent an additional carbon-carbon bond;or P and L are each 0; p1 K is 0, 2, 3 or 4;M is 0, 1, 2 or 3;N is 0 or 1;X is a hydrogen atom;Y is a hydrogen atom, a lower alkyl group of 1-4 carbon atoms, a hydroxy group, a C.sub.1-6 alkoxy group, a C.sub.Type: GrantFiled: December 22, 1981Date of Patent: January 31, 1984Assignee: Schering, AktiengesellschaftInventors: Heinz Gries, Wolfgang Mutzel
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Patent number: 4410519Abstract: An optically active or racemic 2-amino-5-hydroxy-1,2,3,4-tetrahydronaphthalene wherein the nitrogen atom of the amino group carrier two alkyl groups, one of which is unsubstituted and the other is substituted by at least one functional group, or a physiologically hydrolysable ester thereof in free base form or in the form of an acid addition salt thereof is provided which is active against heart circulatory disorders and Morbus Parkinson and inhibits prolactin secretion inhibition.Type: GrantFiled: March 12, 1981Date of Patent: October 18, 1983Assignee: Sandoz Ltd.Inventors: Max P. Seiler, Andre Stoll
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Patent number: 4402975Abstract: A compound represented by the following formula ##STR1## wherein R.sup.1 represents a hydrogen atom, an acyl group or an alkoxycarbonyl group; X.sup.1 represents an alkylene group having 3 to 6 carbon atoms, a 1,4-cyclohexylene group, or a 1,4-phenylene group, the alkylene group may be substituted by an alkyl group having 1 to 6 carbon atoms, and the 1,4-phenylene group may be substituted by 1 or 2 substituents selected from halogen atoms and alkoxy groups having 1 to 6 carbon atoms; R.sup.2 represents a hydrogen atom or a hydroxyl group and R.sup.3 represents hydrogen atom, or R.sup.2 and R.sup.3 together may form an oxo group (.dbd.O), and when X.sup.1 is other than the 1,4-phenylene group, R.sup.2 represents a hydrogen atom and R.sup.3 represents a bond between the carbon atoms to which R.sup.3 is bonded and that carbon atom of X.sup.1 which is adjacent to said carbon atom; X.sup.Type: GrantFiled: July 17, 1981Date of Patent: September 6, 1983Assignee: Teijin LimitedInventors: Toru Takeshita, Kenji Hoshina, Akira Ohtsu, Tatsuyuki Naruchi
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Patent number: 4401676Abstract: Novel .alpha.-ethynyl- and .alpha.-vinyl 3,4-disubstituted phenylalanines are disclosed. The compounds have pharmaceutical activity.Type: GrantFiled: June 1, 1977Date of Patent: August 30, 1983Assignee: Merck & Co., Inc.Inventors: Arthur A. Patchett, David Taub
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Patent number: 4391986Abstract: Threo-3-protected amino-2-hydroxy-4-oxobutanoic acid or its esters represented by the formula: ##STR1## wherein R.sub.1 represents naphthyl or a group of the formula ##STR2## in which R.sub.6 and R.sub.7 represent individually hydrogen, halogen, amino, an amino protected with acyl, lower alkyloxycarbonyl or carbamoyl, hydroxy or protected with acyl, lower alkyloxycarbonyl or carbamoyl, lower alkoxy, lower alkyl or phenyl group; R.sub.2 represents an amine protected with acyl, lower alkyloxycarbonyl or carbamoyl; and R.sub.3 represents hydrogen, lower alkyl having 1 to 6 carbon atoms or benzyl.Type: GrantFiled: November 28, 1980Date of Patent: July 5, 1983Assignee: Nippon Kayaku Kabushiki KaishaInventors: Hamao Umezawa, Takaaki Aoyagi, Tadashi Shirai, Rinzo Nishizawa, Masao Suzuki, Tetsushi Saino
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Patent number: 4386080Abstract: Novel 3,4-disubstituted-N-acylanilines of the formula: ##STR1## wherein R.sup.1, R.sup.2 and ring A are defined in claim 1; wherein R.sup.3 is hydrogen or alkyl of up to 4 carbon atoms, or is joined to R.sup.5 as stated below;wherein R.sup.4 is alkyl of 2 to 4 carbon atoms, or has the formula --CX.sup.1 X.sup.2 X.sup.3 wherein X.sup.1, X.sup.2 and X.sup.3, which may be the same or different, each is hydrogen, fluorine or chlorine; wherein R.sup.5 is hydrogen, hydroxy or alkoxy or acyloxy each of up to 15 carbon atoms, or is joined to R.sup.3 to form an oxycarbonyl group such that together with the ##STR2## part of the molecule it forms an oxazolidinedione group; and wherein R.sup.6 is hydrogen or halogen. These compounds possess antiandrogenic activity and are useful for the treatment of androgen dependent or prostatic diseases. Representative of the compounds is 3,4-dichloro-N-(2-hydroxy-2-p-nitrophenylpropionyl)aniline.Type: GrantFiled: May 21, 1981Date of Patent: May 31, 1983Assignee: Imperial Chemical Industries LimitedInventors: Neville S. Crossley, Alasdair T. Glen, Leslie R. Hughes
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Patent number: 4370497Abstract: The present invention relates to the use of telluroxides as mild and selective oxidizing agents serving to oxidize certain functions, notably >C.dbd.S groups, in the presence of other relatively easily oxidized functions which remain unaffected; telluroxides of interest as oxidizing agents include, for example, compounds of the formula: ##STR1## wherein R and R.sup.1, which may be the same or different, each represent an optionally substituted aryl or heterocyclic group; or R and R.sup.1 together with the tellurium atom therebetween represent a heterocyclic ring, which may contain one or more further heteroatoms, and which may carry substituents and/or fused aromatic rings.Type: GrantFiled: August 7, 1980Date of Patent: January 25, 1983Inventors: Derek H. R. Barton, Steven V. Ley, Clive A. Meerholz
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Patent number: 4366172Abstract: Novel 4-aminocyclohexanols are formulated into pharmaceutical compositions for analgetic purposes in mammals in need of said treatment.Type: GrantFiled: September 29, 1977Date of Patent: December 28, 1982Assignee: The Upjohn CompanyInventor: Daniel Lednicer
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Patent number: 4336400Abstract: Mono-, di- and tri-esters of 3-(hydroxy or hydroxymethyl)-4-hydroxy-alpha-(aminomethyl)benzyl alcohols, obtained by methods involving reduction of the corresponding mono- and di-ester ketones, are useful for producing sympathomimetic effects, such as bronchodilation, of long duration with low cardiovascular stimulating effect, in warm-blooded mammals.Type: GrantFiled: August 30, 1978Date of Patent: June 22, 1982Assignee: Sterling Drug Inc.Inventors: Hiroaki Minatoya, Benjamin F. Tullar, Walter D. Conway
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Patent number: RE32489Abstract: Substituted 2-[1-(oxyamino)alkylidene]-cyclohexane-1,3-diones have herbicidal activity against grassy weeds.Type: GrantFiled: August 30, 1985Date of Patent: September 1, 1987Assignee: Chevron Research CompanyInventor: Tatao Luo