The -c(=x)- Is Bonded Directly To The Ring Nitrogen Of The Five-membered Hetero Ring (e.g., 1-pyrrolidine Carboxanilides, Etc.) Patents (Class 548/538)
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Patent number: 4709053Abstract: The invention relates to a process for the preparation of 4-phenylpyrrole derivatives of the formula I ##STR1## wherein R.sub.n, R.sub.1 and R.sub.2 are as defined in claim 1, which comprises reacting a phenacylamine of formula II ##STR2## with a compound of formula IIIT--CH.dbd.CH--R.sub.1 (III)to give an intermediate of formula IV ##STR3## and cyclizing said intermediate, in the presence of a base, to give the compound I.Important intermediates and novel final products are also described.Type: GrantFiled: September 9, 1985Date of Patent: November 24, 1987Assignee: Ciba-Geigy CorporationInventor: Pierre Martin
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Patent number: 4708954Abstract: Pharmaceutical compositions containing an oxaluric acid derivative of the formula: ##STR1## wherein each of R.sub.1 and R.sub.2, which may be the same or different, is hydrogen; an alkyl group or a cycloalkyl group; or R.sub.1 and R.sub.2 are joined to form a heterocyclic ring with the nitrogen atom to which they are both attached; and R.sub.3 is hydrogen or an alkyl group. These compounds have excellent hypoglycemic effects with low toxcicity and safety.Type: GrantFiled: February 7, 1986Date of Patent: November 24, 1987Assignee: Nippon Zoki Pharmaceutical Co., Ltd.Inventors: Kazuharu Ienaga, Ko Nakamura, Akira Ishii
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Patent number: 4692521Abstract: The invention relates to N-substitutecd acyl lactam compounds of the formula ##STR1## where R is a polyol residue originating from a polyol with the formula R-(OH).sub.x where x is a number.ltoreq.2R' a bivalent cyclic or non-cyclic alkyl, aralkyl, alkaryl or aryl radicalR" a bivalent radical having the following general formula ##STR2## wherein R'" is H, alkyl, cycloalkyl, aryl, alkaryl or aralkyl,R.sup.iv is H, alkyl, cycloalkyl, aryl, alkaryl or aralkyl whereR"' and R.sup.iv may jointly form a substituted or non-substituted cycloalkyl residuen is 0 or 1 and(-L) represents a non-opened lactam ring of the formula ##STR3## wherein Y is hydrocarbon residue with 3-11 carbon atoms. It has been found that this group of compounds is very suitable as activator in the preparation of nylon block copolymers, more specifically in the RIM or RRIM systems.Type: GrantFiled: December 13, 1985Date of Patent: September 8, 1987Assignee: Stamicarbon B.V.Inventors: Jozef J. M. Bongers, Albert A. Van Geenen
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Patent number: 4692520Abstract: The invention relates to the N-substituted acyl-lactam compound of the formula: ##STR1## where R' is a bivalent cyclic or non-cyclic alkyl, aralkyl, alkaryl or aryl radicalR" a bivalent radical having the following general formula ##STR2## wherein R'" is H, alkyl, cycloalkyl, aryl, alkaryl or aralkyl,R.sup.iv is H, alkyl, cycloalkyl, aryl, alkaryl or aralkyl whereR'" and R.sup.iv may jointly form a substituted or non-substituted cycloalkyl residuen is 0 or 1(-L) represents a non-opened lactam ring andx a number>1.It has been found that this group of compounds is very suitable as activator in the preparation of nylon polymers, more specifically in the so-called RIM (Reaction Injection Moulding) or RRIM (reinforced RIM) systems, in which it is highly essential for the polymerization to take effect within a very short time.Type: GrantFiled: December 13, 1985Date of Patent: September 8, 1987Assignee: Stamicarbon B.V. (Subsidiary of DSM)Inventors: Albert A. Van Geenen, Jozef J. M. Bongers
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Patent number: 4691026Abstract: A compound represented by the following formula: ##STR1## wherein R is a C.sub.3 -C.sub.24 olefinically unsaturated organic radical having functionality which renders the nitrogen atom electron deficient, the olefinic unsaturation functionality being polymerizable,R.sup.1 is hydrogen or a C.sub.1 -C.sub.4 alkyl radical, orR and R.sup.1 together with the nitrogen atom can form an olefinically unsaturated 5 to 7-member ring which has functionality that renders the nitrogen atom electron deficient and the olefinic unsaturation functionality is polymerizable,R.sup.2 and R.sup.3 are hydrogen, a C.sub.1 -C.sub.4 alkyl or acyl radical, orR.sup.2 and R.sup.3 together are a C.sub.2 -C.sub.4 alkylene group,R.sup.4 is hydrogen or a C.sub.1 -C.sub.4 alkyl, acyl, ester, amide or acid group, andn is an integer from 1 to 10, provided n is not 1 when R is (meth)acryloyl, R.sup.2 and R.sup.3 are methyl and R.sup.1 and R.sup.4 are hydrogen.Under acidic conditions the above compounds having R.sup.Type: GrantFiled: July 30, 1985Date of Patent: September 1, 1987Assignee: Air Products and Chemicals, Inc.Inventors: Robert K. Pinschmidt, Jr., Dale D. Dixon, William F. Burgoyne, Jr.
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Patent number: 4683304Abstract: The invention relates to a process for preparing an acyl-lactam compound characterized in that the reaction product of a lactam with a dicarboxylic acid anhydride is reacted with a polyol at a temperature of 150.degree. C. at most. These acyl-lactam compounds are very suitable as activator in the preparation of nylon block copolymers, more specifically in the RIM or RRIM systems.Type: GrantFiled: December 13, 1985Date of Patent: July 28, 1987Assignee: Stamicarbon B.V.Inventors: Albert A. Van Geenen, Jozef J. M. Bongers
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Patent number: 4645842Abstract: A novel compound useful in detecting leukocytes, esterase and protease in a test sample. The compound has the structure ##STR1## in which: A is an acid residue, R is lower alkyl, aryl, carboxyl, carboxyl ester, amido or cyano, R* is H or lower alkyl, and X is O, S, or NR', in which R' is H, lower alkyl or aryl.Type: GrantFiled: April 6, 1984Date of Patent: February 24, 1987Assignee: Miles Laboratories, Inc.Inventors: Paul F. Corey, Frederick E. Ward, Kin F. Yip, Meitak T. Yip
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Patent number: 4643758Abstract: N-(Substituted heterocyclic)-2-pyrrolidinone derivatives useful as herbicides both alone and in combination with other herbicides.Type: GrantFiled: November 8, 1984Date of Patent: February 17, 1987Assignee: Eli Lilly and CompanyInventors: Kenneth W. Burow, Jr., James C. Williams, Jr.
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Patent number: 4613356Abstract: Substituted aryloxyphenoxy propionyl thiourea compounds useful as herbicides, and their methods of use, a representative one of which has the structural formula ##STR1## The method comprises applying the above referenced compound to the locus where control is desired.Type: GrantFiled: August 6, 1984Date of Patent: September 23, 1986Assignee: Stauffer Chemical CompanyInventor: Ferenc M. Pallos
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Patent number: 4612313Abstract: The present invention provides phenylacetonitrile derivatives of the general formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5, which can be the same or different, are hydrogen or haolgen atoms or alkyl, alkoxy, nitro, amino or acylamino radicals and two adjacent substituents can together also form a methylenedioxy or ethylenedioxy radical, A is a radical of the general formula: ##STR2## in which R.sub.6 is a straight-chained, cyclic or branched, saturated or unsaturated alkyl radical containing 2 to 12 carbon atoms, R.sub.Type: GrantFiled: September 10, 1985Date of Patent: September 16, 1986Assignee: Boehringer Mannheim GmbHInventors: Herbert Leinert, Wolfgang Kampe, Klaus Strein, Bernd Muller-Beckmann, Wolfgang Bartsch
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Patent number: 4610985Abstract: Allophanate derivatives of the formula ##STR1## in which R.sup.1 and R.sup.2 can be identical or different and represent an aliphatic, cycloaliphatic, araliphatic or aromatic radical each of which is optionally monosubstituted or polysubstituted by identical or different substituents andR.sup.3 represents the radical --XR.sup.4 or --NR.sup.5 R.sup.6,whereinR.sup.4 represents alkyl, alkoxyalkyl, or aryl which is optionally monosubstituted or polysubstituted by identical or different substituents, X represents oxygen or sulphur andR.sup.5 and R.sup.6 are identical or different and represent hydrogen, alkyl, or aryl which is optionally monosubstituted or polysubstituted by identical or different substituents, orR.sup.5 and R.sup.6, together with the nitrogen atom on which they stand, form a saturated heterocyclic radical which is optionally monosubstituted or polysubstituted by identical or different substituents and can be interrupted by further hetero-atoms,which possess fungicidal activity.Type: GrantFiled: April 10, 1985Date of Patent: September 9, 1986Assignee: Bayer AktiengesellschaftInventors: Wolfgang Fuhrer, Engelbert Kuhle, Gerd Hanssler
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Patent number: 4608201Abstract: A process for preparing a lactam imide involves reacting together a lactam, a non-volatile carboxyl group-containing material, and an anhydride of a volatile carboxylic acid with the proviso that an appreciable amount of non-volatile carboxyl group-containing material and volatile carboxylic acid which is generated as the anhydride reacts are both present in the reaction mixture at the same time.Type: GrantFiled: May 21, 1984Date of Patent: August 26, 1986Assignee: PPG Industries, Inc.Inventor: Gregory J. McCollum
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Patent number: 4594343Abstract: Novel 1-[(aminoalkyl and aminoalkylamino)carbonyl and thiocarbonyl]-.alpha.,.alpha.-diaryl-pyrrolidine, piperidine and homopiperidineacetamides and acetonitriles having the formula: ##STR1## wherein; n is zero, one or two;X is oxygen or sulfur;Z is ##STR2## p is 0 to 5 inclusive with the proviso that when Z is ##STR3## p is at least one; Y is aminocarbonyl or cyano;Ar.sup.1 and Ar.sup.2 are 2, 3 or 4-pyrido, phenyl or substituted phenyl;R is hydrogen or loweralkyl;R.sup.1, R.sup.2 and R.sup.3 are hydrogen, cycloalkyl, loweralkyl, phenyl, substituted phenyl, phenylloweralkyl, and R.sup.2 and R.sup.3 taken with the adjacent nitrogen may form a heterocyclic residue, and diastereoisomers when possible and pharmaceutical salts; and the method and pharmaceutical compositions for treating cardiac arrhythmias therewith are disclosed.Type: GrantFiled: October 19, 1984Date of Patent: June 10, 1986Inventors: James R. Shanklin, Jr., James M. Wilkinson, II
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Patent number: 4593102Abstract: Novel pyrrolidine, piperidine and homopiperidinecarboxamide and thiocarboxamide compounds having the formula: ##STR1## wherein X is --S--, --S(O)-- or --S(O).sub.2 --; A is a loweralkalene chain and A.sup.1 and A.sup.2 are alkalene chains when p and d are one; R, R.sup.1 and R.sup.2 are hydrogen, loweralkyl, phenyl cycloalkyl or phenylalkyl and R.sup.1 and R.sup.2 may form a heterocyclic residue with the adjacent nitrogen atom; Q is a selected aromatic radical, and the pharmaceutically acceptable acid addition salts useful as cardiac antiarrhythmia agents are disclosed.Novel chemical intermediates, unsubstituted on pyrrolidine, piperidine and homopiperidine nitrogen but with --(A.sup.2).sub.p --X--(A.sup.2).sub.d --Q side chain are also disclosed.Type: GrantFiled: July 1, 1985Date of Patent: June 3, 1986Assignee: A. H. Robins Company, Inc.Inventor: James R. Shanklin, Jr.
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Patent number: 4582855Abstract: Novel compounds of the general formula ##STR1## wherein Ar represents a substituted or unsubstituted aromatic or heterocyclic group; W represents alkylene of from 1 to about 10 carbon atoms; and B represents --NR.sub.2 COR.sub.1, --NR.sub.2 CONR.sub.1 R.sub.3, --NR.sub.2 SO.sub.2 R.sub.1, --NR.sub.2 SO.sub.2 NR.sub.1 R.sub.3, or --NR.sub.2 COOR.sub.1 wherein R.sub.1, R.sub.2 and R.sub.3 may be the same or different and may be hydrogen, alkyl, alkoxyalkyl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, or aralkyl, except that R.sub.1 is not hydrogen when B is --NR.sub.2 SO.sub.2 R.sub.1 or --NR.sub.2 COOR.sub.1, or R.sub.1 and R.sub.3 may together with N form a 5 to 7 momoered heterocyclic group; and the pharmaceutically acceptable salts thereof. These compounds exhibit .beta.-adrenergic blocking activity and are also useful in the treatment of glaucoma.Type: GrantFiled: November 12, 1981Date of Patent: April 15, 1986Assignee: American Hospital Supply CorporationInventors: Sheung T. Kam, William L. Matier
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Patent number: 4575560Abstract: The invention is insecticidal diaminoguanidine hydrazone compounds which are also effective antifeeding agents for insects and methods for their preparation.Type: GrantFiled: February 25, 1985Date of Patent: March 11, 1986Assignee: American Cyanamid CompanyInventors: Roger W. Addor, Donald P. Wright, Jr., Jack K. Siddens, John J. Hand
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Patent number: 4566900Abstract: Aniline derivatives of the formula ##STR1## where R.sup.1, Y, A, Z and n have the meanings given in the description, are used for controlling undesirable plant growth.Type: GrantFiled: December 1, 1982Date of Patent: January 28, 1986Assignee: BASF AktiengesellschaftInventors: Peter Plath, Ulrich Schirmer, Gernot Reissenweber, Bruno Wuerzer, Guenter Retzlaff
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Patent number: 4559357Abstract: Compounds of the formula ##STR1## and of the isomeric formulae ##STR2## wherein R is alkyl or halogen, R.sub.1 is hydrogen, optionally substituted alkyl or optionally substituted alkenyl, R.sub.2 is hydrogen or methyl, R.sub.3 is hydrogen, alkyl or alkenyl, and X is oxygen or sulfur, including their acid salts, are insecticidally and acaricidally active.Type: GrantFiled: June 6, 1983Date of Patent: December 17, 1985Assignee: Ciba-Geigy CorporationInventors: Jean-Claude Gehret, Walter Traber
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Patent number: 4536598Abstract: A new color-forming 4-(4'-secondary or tertiary-amino)anilino-1-carboxamidonaphthalene dye precursor in a photographic material and process enables formation of a dye image by means of cross-oxidation without the need for a coupling reaction. The color-forming 4-(4'-secondary or tertiary-amino)anilino-1-carboxamidonaphthalene dye precursor is useful in a photographic silver halide material for producing (i) a dye image, or (ii) a dye image and silver image. The exposed photographic material is processed to produce (a) a positive dye image, (b) a negative dye and negative silver image, (c) a negative dye image or (d) a positive dye image and a positive silver image. New naphthoquinoneimide dyes are also described.Type: GrantFiled: March 10, 1983Date of Patent: August 20, 1985Assignee: Eastman Kodak CompanyInventors: James E. Klijanowicz, Csaba A. Kovacs
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Patent number: 4529549Abstract: This invention relates to a novel spergualin-related compound and a process for the production thereof. The novel compound, which has a high antitumor activity, is represented by the general formula ##STR1## wherein R.sub.1 represents a hydrogen atom, hydroxyl group, or an aliphatic acyloxy group having 1 to 10 carbon atoms, R.sub.2 represents an amino acid residue (except for the residue of .alpha.-hydroxyglycine) formed by removing one hydrogen atom and hydroxyl group from respectively the .alpha.- or .omega.-amino group and the .alpha.-carboxyl group of an .alpha.- or .omega.-amino acid, said amino acid residue forming acid amide linkages with the adjacent carbonyl group and amino group, and m is an integer of 4 to 6.Type: GrantFiled: August 18, 1983Date of Patent: July 16, 1985Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu KaiInventors: Hamao Umezawa, Tomio Takeuchi, Rinzo Nishizawa, Katsutoshi Takahashi, Teruya Nakamura, Yoshihisa Umeda
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N-(Alkylsulfonyl)-L-proline amide and N-(alkylsulfonyl)-2-carboxylic acid amide-indoline derivatives
Patent number: 4438031Abstract: Disclosed herein are (lower)alkylsulfonyl derivatives of various proline amides, thiazolidine carboxylic acid amides and indoline-2-carboxylic acid amides, among others, which inhibit angiotensin converting enzyme and are antihypertensive agents.Type: GrantFiled: February 24, 1982Date of Patent: March 20, 1984Assignee: American Home Products CorporationInventors: Michael W. Winkley, Scott J. Childress -
Patent number: 4432985Abstract: Described are compounds of the formula ##STR1## wherein R is hydrogen or loweralkyl; R.sub.1 is --OR.sub.2 or --NR.sub.2 R.sub.3 wherein R.sub.2 and R.sub.3 independently of one another denote hydrogen or loweralkyl; n is 0 or 1; R.sub.4 and R.sub.5 independently of one another denote loweralkyl or together form a 5 or 6 membered cycloalkyl substituted by hydrogen or loweralkyl, and together with the nitrogen atom, form a ring; and pharmaceutically acceptable salts thereof and their use as anticonvulsant agents in a method of controlling convulsions or seizures.Type: GrantFiled: March 15, 1982Date of Patent: February 21, 1984Assignee: Abbott LaboratoriesInventors: Alex M. Nadzan, George R. Granneman
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Patent number: 4389400Abstract: The 2,2-bis(haloalkenyl)-1-substituted-1-cyanoethylene compounds of this invention are effective fungicides. In particular, some of the compounds of this invention are especially effective against Grape Downy Mildew and Rice Blast.Type: GrantFiled: March 25, 1982Date of Patent: June 21, 1983Assignee: Chevron Research CompanyInventor: Andrew W. Ho
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Patent number: 4389401Abstract: This invention relates to novel compounds of the formula ##STR1## wherein R.sup.1 is lower alkenyl or lower alkynyl; R.sup.2 is lower alkenyl, lower alkynyl or cycloalkyl; R.sup.3 is hydrogen; R.sup.4 is alkyl, cycloalkyl or lower alkoxycarbonylalkyl or R.sup.2 and R.sup.3 are joined to form dimethyleneoxy (i.e. --CH.sub.2 OCH.sub.2 --) or R.sup.3 and R.sup.4 taken together with the nitrogen to which they are attached, form a 5- to 6- membered heterocyclic ring, compositions containing said compounds and a method of employing said compounds as arthropod repellents.Type: GrantFiled: July 10, 1979Date of Patent: June 21, 1983Assignee: Rohm and Haas CompanyInventor: Joel R. Smolanoff
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Patent number: 4379785Abstract: What are disclosed are sulfonyl ureas of the formula ##STR1## in which R.sup.1, X and Y are as defined in the specification, and their physiologically acceptable salts, pharmaceutical formulations on the basis of these compounds, and their use in the treatment of diabetes.Type: GrantFiled: December 17, 1980Date of Patent: April 12, 1983Assignee: Hoechst AktiengesellschaftInventors: Rudi Weyer, Volker Hitzel, Karl Geisen, Gunter Regitz
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Patent number: 4374991Abstract: This invention relates to a method of using compounds of the formula: ##STR1## wherein R.sup.1 is hydrogen, alkyl or alkenyl; R.sup.2 is hydrogen, alkyl, cycloalkyl or mononuclear aryl or R.sup.1 and R.sup.2, taken together with the carbon atom to which they are attached, form a cycloalkyl or cycloalkoxyalkyl; R.sup.3 is hydroxy, alkyl, alkoxycarbonyl, hydroxy lower alkyl or a radical of the formula: --C(.dbd.Y)NR.sup.4 R.sup.5 wherein R.sup.4 is hydrogen, alkyl, alkenyl, R.sup.5 is alkyl, alkenyl, alkoxyalkyl, carbalkoxy, mononuclear aryl, or R.sup.4 and R.sup.5 may be joined together with the nitrogen atom to which they are attached to form a 5 to 7 membered heterocyclic ring having from 1 to 3 hetero atoms; Y is O or S; X is alkyl, alkoxycarbonylalkyl or cyano; m is an integer of 0 to 2 and n and n' are integers each having a value of 1 to 2 and the dotted line indicates an optional double bond anywhere in the ring, compositions containing said compounds as insect repellents and to novel compounds.Type: GrantFiled: December 29, 1981Date of Patent: February 22, 1983Assignee: Rohm and Haas CompanyInventor: Joel R. Smolanoff
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Patent number: 4362546Abstract: Tetrahydrophthalamide derivatives of the general formula: ##STR1## wherein X.sub.1 is hydrogen or halogen; X.sub.2 is halogen, alkoxy or substituted benzyloxy; X.sub.3 is hydrogen, alkoxy or alkenyloxy; R and R' are the same or different alkyl, cycloalkyl, alkenyl or phenyl, each of which may be optionally substituted, or may jointly, together with nitrogen atom adjacent to R and R', form aliphatic heterocyclic ring containing one or two nitrogens or nitrogen and oxygen, which have a herbicidal activity against a broad spectrum of monocotyledonous and dicotyledonous weeds.Type: GrantFiled: May 27, 1980Date of Patent: December 7, 1982Assignee: Takeda Chemical Industries, Ltd.Inventor: Hiroshi Nagase