Chalcogen Bonded Directly To Ring Carbon Of The Piperidine Ring Patents (Class 546/242)
  • Patent number: 4976889
    Abstract: 4-Formylaminopiperidine derivatives of the formula (I) ##STR1## where n is 1 or 2, R.sup.1 to R.sup.4 are each alkyl or R.sup.1 and R.sup.2 or R.sup.3 and R.sup.4 are tetra- or pentamethylene, R.sup.5 is hydrogen or alkyl, R.sup.6 is hydrogen, unsubstituted or substituted alkyl, alkenyl, aralkyl or acyl, and, when n is 1, Y is hydrogen, unsubstituted or substituted alkyl, alkenyl, cycloalkyl, bicycloalkyl, aralkyl, aryl, alkyl containing heterocyclic radicals, or ##STR2## or, when n is 2, Y is alkylene, cycloalkylene, aralkylene or arylene or is alkylene which is interrupted by oxygen, nitrogen, sulfur or a 5-membered or 6-membered heterocyclic structure, and their acid addition salts have very good stabilizing properties in plastics.
    Type: Grant
    Filed: November 14, 1988
    Date of Patent: December 11, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Alexander Aumueller, Peter Neumann, Hubert Trauth
  • Patent number: 4972009
    Abstract: Compounds possessing both a hindered amine moiety, such as a derivative of 2,2,6,6-tetramethylpiperidine, and a nitrone moiety are valuable stabilizers for protecting polymer compositions against the deleterious effects of actinic light and from the adverse effects of high temperature polymer processing environments. Additionally, the instant compounds present the opportunity for grafting onto preformed polymer backbones.
    Type: Grant
    Filed: August 18, 1989
    Date of Patent: November 20, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Joseph Suhadolnik, Ramanathan Ravichandran
  • Patent number: 4970307
    Abstract: A process for formation of a base from a base precursor, which comprises decomposing the base precursor in the presence of a catalyst. The base precursor has the following formula (I) or (II):(R.sup.1 --C.tbd.C--CO.sub.2 H).sub.x .multidot.B (I)R.sup.2 (--C.tbd.C--CO.sub.2 H).sub.2 .multidot.B.sub.y (II)wherein R.sup.1 is a monovalent group selected from the group consisting of hydrogen, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aryl group, a heterocyclic group, an aralkyl group, an acyl group, an alkoxycarbonyl group, carbamoyl, --CO.sub.2 M (M is an alkali metal) and --CO.sub.2 H.B, each of which may have one or more substituent groups; R.sup.
    Type: Grant
    Filed: August 13, 1987
    Date of Patent: November 13, 1990
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Keiji Takeda, Jiro Tsukahara, Kozo Sato
  • Patent number: 4942238
    Abstract: Compounds of formula I ##STR1## wherein R is hydrogen, methyl or cyano, and R' is hydrogen, C.sub.1 -C.sub.8 alkyl or phenyl, are suitable for copolymerization with ethylenically unsaturated monomers to form crosslinked copolymers which are stabilized against light.
    Type: Grant
    Filed: May 22, 1989
    Date of Patent: July 17, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Gerhard Rytz, Mario Slongo
  • Patent number: 4940795
    Abstract: Heterocyclic spiro compounds represented by the following general formula and salts thereof: ##STR1## The above compounds act upon muscarinic acetylcholine receptors, thereby activating the acetylcholine nervous functions in the central nervous system.
    Type: Grant
    Filed: October 5, 1988
    Date of Patent: July 10, 1990
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Shin-ichi Tsukamoto, Hitoshi Nagaoka, Shinji Usuda, Masatomi Harada, Toshinari Tamura
  • Patent number: 4940705
    Abstract: N-substituted derivatives of 1-desoxynojirimycin and 1-desoxymannojirimycin of the formula ##STR1## in which one of R and R' are hydroxyl and the other is hydrogenn is a number from 1 to 6R.sup.1 is hydrogen, alkyl or benzyl andR.sup.2 is alkyl which is optionally substituted by an optionally substituted aryl or by pyridyl, thienyl, furyl, pyrimidyl, pyrazinyl or quinolyl or R.sub.1 is cycloalkyl or R.sup.2 is optionally substituted by aryl or R.sup.2 is a saturated bridged heterocycle or R.sup.1 and R.sup.2 together can form a heterocyclic ring which is optionally substituted. These compounds are useful in the treatment of and prophylaxis of viral infections.
    Type: Grant
    Filed: October 26, 1988
    Date of Patent: July 10, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Horst Boshagen, Bodo Junge, Arnold Paessens, Matthias Schuller
  • Patent number: 4931562
    Abstract: A bleaching composition comprises:(A) hydrogen peroxide and/or a hydrogen peroxide addition compound such as a percarbonate; and(B) at least one activator which is a nitrogen-containing heterocyclic compound in which a halogen atom is substituted for the hydrogen atom of the secondary amino group or a non-heterocyclic N-halo-hindered amine compound, the hydrolysis constant of the activator being within the range of 1.times.10.sup.-10 to 5.times.10.sup.-6 (at 25.degree. C.). Examples of the activator include 1-chloro-piperidine, 1-chloro-2-methyl-piperidine, 1-chloro-isonipecotic acid, 1-chloro- -hexamethyleneimine and 1-chloro-.epsilon.-caprolactam. The bleaching-detergent composition may also contain the components (A) and (B) together with a surfactant. These compositions exhibit an excellent effect concerning bleaching at low temperature, but hardly affect the colors of colored and patterned clothes.
    Type: Grant
    Filed: January 11, 1989
    Date of Patent: June 5, 1990
    Assignees: Lion Corporation, Sankyo Company Limited
    Inventors: Yasuhiro Akabane, Takamitsu Tamura, Masami Fujiwara
  • Patent number: 4910310
    Abstract: Novel intermediates and method for the chemical synthesis of N-substituted 1,5-dideoxy-1,5-imino-L-fucitol derivatives are provided. A preferred intermediate is 1,5-dideoxy-1,5-imino-3, 4-O-isopropylidene-L-fucitol which is used to prepare the HIV inhibitor 1,5-dideoxy-1,5-imino-[N-.omega.-methyl caproate]-L-fucitol. These compounds are prepared in a short synthesis from the known compound 2,3-O-isopropylidene-D-lyxono-1,4-lactone or in a multi-step synthesis from D-galactose.
    Type: Grant
    Filed: October 3, 1988
    Date of Patent: March 20, 1990
    Assignee: G. D. Searle & Co.
    Inventors: Arthur L. Campbell, James R. Behling, Kevin A. Babiak, John S. Ng, Richard A. Mueller, George W. J. Fleet
  • Patent number: 4889953
    Abstract: Compounds of the formula: ##STR1## wherein R.sup.1 is a higher alkyl group which may be substituted; R.sup.2 is a hydrogen, a lower alkyl group which may be substituted, a lower alkanoyl group which may be substituted or a lower alkylthiocarbamoyl group; R.sup.3 is a primary to tertiary amino group or a quaternary ammonium group; and n is 2 or 3, and salts thereof, have antitumor activity and platelet activating factor inhibitory activity.
    Type: Grant
    Filed: July 22, 1987
    Date of Patent: December 26, 1989
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Keizo Inoue, Hiroaki Nomura, Tetsuya Okutani
  • Patent number: 4873329
    Abstract: A compound of the formula ##STR1## wherein X has the formula ##STR2## wherein ring A is phenyl, naphthyl or heterocyclic; wherein R.sup.1 is hydrogen, alkyl, alkanoyl or aroyl; wherein R.sup.2, R.sup.3 and R.sup.4, which may be the same or different, each is an electron withdrawing substituent selected from halogeno, nitro, cyano, trifluoromethyl, alkylthio, alkylsulphinyl and alkylsulphonyl or each is hydrogen, alkyl, alkoxy or dialkylamino provided that when ring A is phenyl or naphthyl at least one of R.sup.2, R.sup.3 and R.sup.4 is an electron-withdrawing substituent; wherein R.sup.5 and R.sup.6, which may be the same or different, each is hydrogen, halogeno or alkyl; wherein R.sup.7 is alkyl or halogenoalkyl; and wherein R.sup.8 is carbamoyl, alkyl, cycloalkyl, alkenyl, alkynyl, halogenoalkyl, halogenoalkenyl, halogenoalkynyl, alkanoyl, alkylcarbamoyl, dialkylcarbamoyl or aroyl; or wherein R.sup.
    Type: Grant
    Filed: February 21, 1985
    Date of Patent: October 10, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: Leslie R. Hughes, John Oldfield, Howard Tucker
  • Patent number: 4871747
    Abstract: A 3-amino-4,5-dihydroxy-piperidine compound of the formula (I) ##STR1## in which R.sup.1 represents hydrogen, alkyl having up to 8 carbon atoms, aralkyl having 7 to 14 carbon atoms, or represents a group of the formula ##STR2## R.sup.4 denotes straight-chain or branched alkyl having up to 8 carbon atoms, straight-chain or branched alkoxy having up to 8 carbon atoms, or aralkoxy having up to 10 carbon atoms, andR.sup.2 and R.sup.3 represent hydrogen or represent the group NHR.sup.5,R.sup.5 having the same meaning as R.sup.1 and being identical to or different from the latter,with the proviso that, in every case, one substituent of R.sup.2 or R.sup.3 represents hydrogen and the other substituent of R.sup.2 or R.sup.3 represents NHR.sup.5, and physiologically acceptable salts thereof. Such compound is useful to treat prediabetes, gastritis, constipation, caries, atherosclerosis, obesity, diabetes and hyperlipoproteinaemia.
    Type: Grant
    Filed: December 3, 1986
    Date of Patent: October 3, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunther Kinast, Matthias Schuller, Theo Schroder
  • Patent number: 4831134
    Abstract: 1-Hydroxy-2,2,6,6,-tetraalkylpiperidine derivatives are effective as light stabilizers in a variety of substrate systems.
    Type: Grant
    Filed: September 21, 1987
    Date of Patent: May 16, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Ronald A. E. Winter, James P. Galbo
  • Patent number: 4831146
    Abstract: This invention relates to an improved catalytic process for producing 2,2,6,6-tetraalkyl-4-oxopiperidines by the reaction of a ketone and ammonia. The improvement resides in using a catalytic amount of a super acid, i.e., a perfluorinated sulfonic acid polymer or perfluorinated alkyl sulfonic acid as the catalyst.
    Type: Grant
    Filed: March 21, 1988
    Date of Patent: May 16, 1989
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Denise B. Taylor, Barton Milligan
  • Patent number: 4824884
    Abstract: Amic acids, cyclic imides and mixtures thereof which contain both diacyl hydrazide functionalities and hindered amine functionalities are prepared by reacting non-halogenated cyclic anhydrides with hindered amine light stabilizers containing reactive hydrazido funtionalities in inert solvents or in inert polymeric compositions in a melt blending step. The compositions protect polymeric compositions against the degradative effects of heat and light.
    Type: Grant
    Filed: August 12, 1987
    Date of Patent: April 25, 1989
    Assignee: Pennwalt Corporation
    Inventors: Ronald E. MacLeay, Robert T. Kazmierczak
  • Patent number: 4820702
    Abstract: Compounds of formula: ##STR1## in which R and R' denote an alkyl radical having 1 to 7 carbon atoms; R.sub.1 denotes hydrogen or an alkyl radical having 1 to 7 carbon atoms; and R.sub.2 and R.sub.3 denote, separately, an alkyl radical having 1 to 7 carbon atoms or a phenyl radical, or, together with the carbon atom to which they are attached, a cycloalkyl radical having at most 7 carbon atoms; n may assume the values 2 or 3; and their pharmaceutically acceptable salts.Application as a cardiovascular medicinal product.
    Type: Grant
    Filed: December 22, 1987
    Date of Patent: April 11, 1989
    Assignee: Riom Laboratories C.E.R.M.
    Inventors: Patrick Carlier, Jacques A. Simond, Andre J. Monteil
  • Patent number: 4808582
    Abstract: Compounds of formula: ##STR1## wherein: Ar is an aromatic group; R and R.sub.1 are H or CH.sub.3 ; A represents a nitrogenized heterocyclic radical; B is OH or forms with the adjacent CO group, either an amido group, or a carbonyloxy group; R.sub.2 and R.sub.3 are H or alkyl; m=0 or 1; and n=0, 1, 2 or 3.These compounds are useful as drugs having stimulating, protecting and/or correcting activities of the cerebral functions.
    Type: Grant
    Filed: March 19, 1987
    Date of Patent: February 28, 1989
    Assignee: Delalande S.A.
    Inventors: Alain Y. Platel, Guy R. Bourgery, Patrick G. Guerret
  • Patent number: 4806650
    Abstract: A process for preparing a 1-deoxynojirimycin of the formula ##STR1## in which R is hydrogen, optionally substituted alkyl or aralkyl, which comprises converting D-glucose to an aminosorbitol ##STR2## protecting the amino group of the aminosorbitol with an alkalinically detachable group to form the protected compound of the formula ##STR3## in which X is an alkalinically detachable protective group, microbiologically oxidizing the protected compound to an oxidation product of the formula ##STR4## alkalinically splitting off the protective group X to form an aminosorbose of the formula ##STR5## and reducing the aminosorbose.
    Type: Grant
    Filed: April 2, 1987
    Date of Patent: February 21, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Theo Schroder, Mathias Stubbe
  • Patent number: 4797486
    Abstract: Certain trans-3-[3-(3-hydroxy-2-piperidyl)-2-oxopropyl]thieno[3,2-d]pyrimidin-4(3H )-one and furo[3,2-d]pyrimidin-4(3H)-one derivatives, a method of using same as anticoccidial agents, intermediates therefor, and a process for certain intermediates therefor.
    Type: Grant
    Filed: October 14, 1987
    Date of Patent: January 10, 1989
    Assignee: Pfizer Inc.
    Inventors: Edward A. Glazer, James W. McFarland
  • Patent number: 4774332
    Abstract: A compopund containing one or more units of formula I ##STR1## in which R.sub.1 is --CH.sub.2 C.sub.1-4 alkyl or --CH.sub.3 or both groups R.sub.1 form --(CH.sub.2).sub.5 --;R.sub.2 is --CH.sub.2 C.sub.1-4 alkyl or --CH.sub.3 or both groups R.sub.2 form --(CH.sub.2).sub.5 --;R.sub.3 is furylmethyl, unsubstituted C.sub.1-18 alkyl; C.sub.1-4 alkyl monosubstituted by phenyl, the phenyl group of which is unsubstituted or substituted by 1 to 3 groups selected from --OH and C.sub.1-8 alkyl; C.sub.2-8 alkyl monosubstituted by C.sub.1-4 alkoxy; phenyl, unsubstituted or substituted by 1 to 3 groups selected from C.sub.1-8 alkyl and --OH; or cyclohexy, unsubstituted or monosubstituted by C.sub.1-8 alkyl or --OH.These compounds are useful as light stabilizers for polymeric material.
    Type: Grant
    Filed: July 11, 1986
    Date of Patent: September 27, 1988
    Assignee: Sandoz, Ltd.
    Inventor: Lajos Avar
  • Patent number: 4746655
    Abstract: Novel aromatic-spiropiperidineoxazepinones and thiones exhibiting antihistamine activity are disclosed having the formula: ##STR1## wherein A represents an aromatic ring, selected from benzo when Z is carbon or pyrido[3,2-f] when Z is nitrogen either of which rings may be optionally substituted on carbon;B is selected from oxygen or sulfur;R.sup.1 is selected from the group consisting of loweralkyl, cycloalkyl, cycloalkyl-loweralkyl or phenyl-loweralkyl of which phenyl may be optionally substituted;R is selected from the group consisting of loweralkyl, cycloalkyl or phenyl-loweralkyl of which phenyl may be optionally substituted and the pharmaceutically acceptable salts thereof and novel chemical intermediates in the preparation thereof.
    Type: Grant
    Filed: June 10, 1987
    Date of Patent: May 24, 1988
    Assignee: A. H. Robins Company, Incorporated
    Inventor: Albert D. Cale, Jr.
  • Patent number: 4735952
    Abstract: This invention provides a piperidine compound of the formula: ##STR1## wherein R.sup.1 is hydrogen or trihalomethyl,R.sup.2 is hydrogen or protected carboxy,R.sup.3 is heterocyclic group or aryl which may be halogen substituted, andX is --S--, ##STR2## --O--, --NH-- or lower alkylene which may be hydroxy substituted, and pharmaceutically acceptable salt thereof, These compounds possess hypotensive activity and are useful as anti-hypertensive agents. The invention further relates to processes for the preparation of these compounds and pharmaceutical compositions comprising compounds of the above formula.
    Type: Grant
    Filed: January 24, 1986
    Date of Patent: April 5, 1988
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Ikuo Ueda, Masaaki Matsuo, Kiyoshi Taniguchi, Takatomo Ogahara
  • Patent number: 4734502
    Abstract: 2,2,6,6-tetramethyl-4-oxopiperidine is prepared from acetone and ammonia in the presence of catalytic amounts of active halogen compounds selected from sulfonylhalides, sulfurylhalides, N-haloamides, N-haloimides, .beta.-haloesters, .alpha.-haloketones, .alpha.-halohydroxy compounds, and .beta.-halonitriles.
    Type: Grant
    Filed: December 22, 1986
    Date of Patent: March 29, 1988
    Assignee: ICI Americas Inc.
    Inventors: Walter M. Kruse, John F. Stephen
  • Patent number: 4731448
    Abstract: There is disclosed a process for the preparation of 1-(2-hydroxyethyl-2,2,6,6-tetramethyl-4-piperidinol from triacetoneamine, which comprises first reducing triacetoneamine in water and/or a polar organic solvent by catalytic hydrogenation to 2,2,6,6-tetramethyl-4-piperidinol, and adding a catalytic amount of acid to the resultant solution, without isolation of the intermediate, after optional concentration of the solution by distillation, and subsequently reacting the 2,2,6,6-tetramethyl-4-piperidinol with ethylene oxide.1-(2-Hydroxyethyl)-2,2,6,6-tetramethyl-4-piperidinol is a useful light and heat stabilizer for plastics and is, in addition, a valuable intermediate for the synthesis of further light stabilizer additives.
    Type: Grant
    Filed: December 3, 1986
    Date of Patent: March 15, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Heinz Issler, Siegfried Kintopf, Lutz Konig, Hans Stephan
  • Patent number: 4663459
    Abstract: A process is provided for the preparation of 2,2,6,6-tetramethyl-4-oxopiperidine, reacting acetone with ammonia in the presence of a catalytically effective amount of an organic carboxylic acid halide.
    Type: Grant
    Filed: February 14, 1985
    Date of Patent: May 5, 1987
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Tohru Haruna, Atsushi Nishimura, Kazuo Sugibuchi
  • Patent number: 4661597
    Abstract: A process is provided for the preparation of 2,2,6,6-tetramethyl-4-oxopiperidine, reacting acetone with 2,2,4,4,6-pentamethyl-2,3,4,5,-tetrahydropyrimidine in the presence of a catalytically effective amount of an organic carboxylic acid halide.
    Type: Grant
    Filed: February 14, 1985
    Date of Patent: April 28, 1987
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Tohru Haruna, Atsushi Nishimura, Kazuo Sugibuchi
  • Patent number: 4654433
    Abstract: A simple single step process for preparing alkyl and substituted alkyl esters of amino acids is described. The products are bioactive compounds including compounds useful as antihypertensive agents.
    Type: Grant
    Filed: January 14, 1985
    Date of Patent: March 31, 1987
    Assignee: Merck & Co., Inc.
    Inventor: David L. Hughes
  • Patent number: 4649167
    Abstract: Compounds having the formula ##STR1## where R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.5 are independently selected from hydrocarbons, n is an integer of 1 to 15, and Y is H, OH, O, R where R is a hydrocarbon are useful as stabilizers for polymers against the detrimental effects produced by exposure to actinic radiation, such as visible or ultraviolet light rays.
    Type: Grant
    Filed: November 14, 1985
    Date of Patent: March 10, 1987
    Assignee: Pennwalt Corporation
    Inventors: Ludwig K. Huber, James L. Reilly
  • Patent number: 4639436
    Abstract: The invention includes certain 3,4,5-trihydroxypiperidine compounds, methods for their preparation, compositions containing said 3,4,5-trihydroxypiperidine compounds and methods for the use of said compounds and compositions.The subject matter of the invention is useful against diabetes, hyperlipaemia and adiposity as well as in animal nutrition.
    Type: Grant
    Filed: August 23, 1978
    Date of Patent: January 27, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bodo Junge, Hans P. Krause, Lutz Muller, Walter Puls
  • Patent number: 4638060
    Abstract: Antibacterial activity is exhibited by compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: April 29, 1985
    Date of Patent: January 20, 1987
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Joseph E. Sundeen, William H. Koster, Robert Zahler
  • Patent number: 4621110
    Abstract: Alkyl-substituted 4-methyl-piperidine derivatives having formula: ##STR1## wherein X is selected from the radicals: --N R.sub.12 R.sub.13 ; ##STR2## and --O--R.sub.17 Use of the alkyl-substituted 4-methyl-piperidine derivatives of general formula (I) as stabilizers of polymeric substances and polymeric compositions stabilized with said piperidine derivatives.
    Type: Grant
    Filed: January 17, 1984
    Date of Patent: November 4, 1986
    Assignee: Montedison S.p.A.
    Inventor: Piero Di Battista
  • Patent number: 4618634
    Abstract: Novel compounds containing piperidine groups, of the general formula ##STR1## in which R.sub.1 is hydrogen, O--, cyanomethyl, C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.12 -alkenyl or -alkynyl, C.sub.7 -C.sub.12 -aralkyl or C.sub.1 -C.sub.12 -acyl, m is an integer from 1 to 12, n is an integer from 1 to 3 and A is an amine radical, are suitable as light stabilizers, heat stabilizers and oxidation stabilizers for synthetic polymers. Processes for their preparation are also described.
    Type: Grant
    Filed: February 27, 1985
    Date of Patent: October 21, 1986
    Assignee: Ciba-Geigy S.p.A.
    Inventors: Giuseppe Cantatore, Valerio Borzatta
  • Patent number: 4614537
    Abstract: N-Acyl-piperidone ketal compounds of the formula ##STR1## in which R.sup.1 represents alkyl or halogen,R.sup.2 represents halogen,R.sup.3 represents alkyl andR.sup.4 represents alkyl, orR.sup.3 and R.sup.4 together represent an optionally branched alkylene chain, andR.sup.5, R.sup.6, R.sup.7 and R.sup.8 independently of one another represent hydrogen or alkyl,and their use as antidotes for protecting crop plants from herbicidal damage.
    Type: Grant
    Filed: October 25, 1983
    Date of Patent: September 30, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Jochem Riebel, Ludwig Eue, Wilfried Faust, Uwe Priesnitz
  • Patent number: 4611058
    Abstract: The invention relates to a process for preparing 1,5-didesoxy-1,5-imino-D-glucitol (desoxynojirimicin) and N-derivative thereof, which are known to be powerful inhibitors for .alpha.-glycosidases. The process of the invention involves reducing with a complex borohydride, a 6-amino-6-desoxy-L-sorbose.
    Type: Grant
    Filed: May 14, 1985
    Date of Patent: September 9, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventor: Wolfgang Koebernick
  • Patent number: 4548639
    Abstract: N-Acyl-piperidone ketal compounds of the formula ##STR1## in which R.sup.1 represents alkyl or halogen,R.sup.2 represents halogen,R.sup.3 represents alkyl andR.sup.4 represents alkyl, orR.sup.3 and R.sup.4 together represent an optionally branched alkylene chain, andR.sup.5, R.sup.6, R.sup.7 and R.sup.8 independently of one another represent hydrogen or alkyl,and their use as antidotes for protecting crop plants from herbicidal damage.
    Type: Grant
    Filed: September 28, 1982
    Date of Patent: October 22, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Jochem Riebel, Ludwig Eue, Wilfried Faust, Uwe Priesnitz
  • Patent number: 4537963
    Abstract: Process for preparing analgesic and narcotic antagonistic isoquinolines comprising:(a) contacting and reacting a lithiated anisole or alkyl phenyl ether, optionally substituted at the 3-position to the lithium atom, with a 4-piperidone to yield a 4-aryl-4-piperidinol;(b) dehydrating the piperidinol to a 4-aryl-1,2,3,6-tetrahydropyridine;(c) metalating and acylating the 1,2,3,6-tetrahydropyridine to yield a 1-(4-aryl-1,2,3,4-tetrahydropyrid-4-yl)-4-hydroxy-1-butanone;(d) reducing the ketone moiety of the butanone to yield a 5-aryl-7-oxa-2-azabicyclo[3,2.1]-octane-6-propanol;(e) converting the alcohol moiety of the propanol to L to yield a 5-aryl-6-[3-(L)propyl]-7-oxa-2-azabicyclo[3.3.1]octane in which L is a leaving group selected from the group consisting of --Cl, --Br, --I, p--MeC.sub.6 H.sub.4 SO.sub.3 -- and MeSO.sub.3 --.
    Type: Grant
    Filed: August 11, 1983
    Date of Patent: August 27, 1985
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Ashokkumar B. Shenvi
  • Patent number: 4536581
    Abstract: A process for preparing 2,2,6,6-tetramethyl-4-piperidone from ammonia and acetone, wherein acetone and ammonia are reacted in a single stage for a time of 2 to 8 hours in an acetone:ammonia molar ratio of 20:1 to 4:1, at a temperature of 50.degree. to 120.degree. C. and at a pressure of 1 to 50 atmospheres, in the presence of 0.001-0.1 moles of acid catalysts per mole of acetone used in the reaction.
    Type: Grant
    Filed: May 18, 1983
    Date of Patent: August 20, 1985
    Assignee: Ciba-Geigy S.p.A.
    Inventors: Giuseppe Cantatore, Paolo Cassandrini
  • Patent number: 4529760
    Abstract: Oligomers of 2,2,6,6-tetramethylpiperidinol polycarboxylic acid esters are provided having the formula: ##STR1## wherein: Z is the residue of an aliphatic or aromatic or nitriloaliphatic or hydroxy aliphatic polycarboxylic acid having from three to six carboxylic acid groups and from one to thirty carbon atoms; ##STR2## wherein R.sub.3 is hydrogen, alkyl and hydroxyalkyl having from one to about twenty carbon atoms; cycloalkyl having from six to about twenty carbon atoms; aryl having from six to about twenty carbon atoms; or cycloalkylene with the N in the ring and having from two to five carbon atoms;R is alkylene having from two to about twelve carbon atoms; cycloalkylene having from three to about twelve carbon atoms; phenylene having from six to about twenty carbon atoms; mixed alkylenecycloalkylene or alkylene phenylene or oxyalkylene having from two to about twelve carbon atoms; ##STR3## wherein R.sub.4 is alkyl having from one to about six carbon atoms;R.sub.
    Type: Grant
    Filed: November 1, 1983
    Date of Patent: July 16, 1985
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: William E. Leistner, Motonobu Minagawa, Yutaka Nakahara, Tohru Haruna, Atsushi Nishimura
  • Patent number: 4522945
    Abstract: Novel quinazoline derivatives, comprising in the heterocyclic part of their quinazoline nucleus at least one carbonyl or thiocarbonyl group and a particularly substituted piperidinyl-alkyl side chain, said compounds being potent serotonin-antagonists.
    Type: Grant
    Filed: March 26, 1982
    Date of Patent: June 11, 1985
    Assignee: Janssen Pharmaceutica N.V.
    Inventors: Jan Vandenberk, Ludo Kennis, Marcel Van der Aa, Albert Van Heertum
  • Patent number: 4515974
    Abstract: Fumaric acid monoesters can be prepared by introducing a hydroxyl compound at a rate corresponding to the progress of the reaction into a solution or a melt of maleic anhydride, which may optionally be substituted, if appropriate in the presence of a cis-trans catalyst. New fumaric acid monoesters can be formed by the process.
    Type: Grant
    Filed: June 25, 1982
    Date of Patent: May 7, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wilfried Zecher, Rudolf Merten
  • Patent number: 4511722
    Abstract: Cyclic N-vinylacylamines are prepared by heating carbonic acid esters of cyclic N-2-hydroxyethylacylamines in the presence of a catalytic amount of alkali or alkaline earth metal compound having an alkaline reaction and subsequently distilling the reaction mixture.Cyclic N-vinylacylamines are valuable precursors for preparing plant protection agents and medicaments and serve as polymerization and copolymerization components for preparing plastics, surface coatings, paints and ion exchange materials.
    Type: Grant
    Filed: February 16, 1983
    Date of Patent: April 16, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinrich Krimm, Hans-Josef Buysch, Peter M. Lange, Reinhold Klipper
  • Patent number: 4500446
    Abstract: A stabilization mixture is described for use with polymeric materials, the mixture evidencing high stabilization efficiency against the effect of ultraviolet radiation which being of low toxicity. The mixture comprises from 80-100%, by weight, of a mixture of 2,2,6,6-tetramethyl-4-piperidinol esters and from 0-20%, by weight, of the ammonium carboxylates thereof. The mixture is prepared by heating derivatives of 2,2,6,6-tetramethyl-4-piperidinol with mixtures of stearic, palmitic, heptadecanic, myristic and oleic acids at temperatures ranging from 150-260 degrees C.
    Type: Grant
    Filed: September 23, 1982
    Date of Patent: February 19, 1985
    Assignee: Chemicke zavody Juraja Dimitrova, narodny podnik
    Inventors: Julius Durmis, Alojz Balogh, Milan Karvas, Maria Hrachovcova, Jan Masek, Pavol Caucik, Marta Povazancova
  • Patent number: 4499273
    Abstract: There are disclosed new organic peroxides having two peroxy functional groups and containing in their molecule an atom of salified aminic nitrogen, having the general formula: ##STR1## in which: R.sub.1, R.sub.2 are each an alkyl radical having 1 to 8 carbon atoms, optionally aryl-substituted, preferably a tertiary alkyl group such as t.butyl, t.amyl, t.octyl and cumyl;R.sub.3 is a hydrogen, an alkyl radical having 1 to 8 carbon atoms, a cycloalkyl having 5-6 carbon atoms in the ring, an aryl, an arylalkyl optionally halogen, alkoxy-, carboalkoxy-, alkyl-, mono- or poly-substituted;R.sub.4 is the methylene, ethylene or trimethylene radical, optionally halogen-, alkoxy-, carboalkoxy-, aryl-, alkyl-, mono- or poly-substituted;R.sub.
    Type: Grant
    Filed: December 21, 1982
    Date of Patent: February 12, 1985
    Inventors: Alberto Fontana, Renzo Fontanelli, Egeo Sacrini, Osvaldo Cicchetti
  • Patent number: 4496732
    Abstract: A stereoselective reduction of 2- or 3-substituted 4-piperidones of the formula ##STR1## where R.sub.1 is hydrogen, loweralkyl or benzyl and R.sub.2 is methyl or ethyl, to the di-equatorial isomer of the corresponding 4-piperidinol is described. Said reduction is conducted by use of sodium borohydride in a protic solvent medium at a temperature substantially lower than ambient temperature in the presence of an effective amount of an inorganic acid. Under favorable reaction conditions, the stereoselectivity of the reduction is so high that simple crystallization of the reaction product affords the pure isomer in a commercially acceptable and advantageous process.
    Type: Grant
    Filed: March 14, 1983
    Date of Patent: January 29, 1985
    Assignee: Hoechst-Roussel Pharmaceuticals Inc.
    Inventors: George E. Lee, Thomas B. K. Lee
  • Patent number: 4487887
    Abstract: Polymers of diallyl amino-4-(2,2,6,6-tetramethyl piperidyl) carboxylic acid esters and amides are provided, having a molecular weight within the range from about 800 to about 20,000, and derived from a monomer having the formula: ##STR1## wherein: R is alkylene or alkyleneoxy having from one to about six carbon atoms and m is 0 or 1;R.sub.1 is selected from the group consisting of hydrogen; oxyl; alkyl and hydroxyalkyl having from one to about eighteen carbon atoms; alkylaryl having from seven to about eighteen carbon atoms; epoxy alkyl having from three to about eighteen carbon atoms; and acyl having from two to about eighteen carbon atoms; andY is selected from the group consisting of ##STR2## where R.sub.2 and R.sub.3 are hydrogen or alkyl having from one to about eight carbon atoms and n is 0 or 1;Z is selected from the group consisting of ##STR3## in which R.sub.4, R.sub.5 and R.sub.
    Type: Grant
    Filed: September 9, 1983
    Date of Patent: December 11, 1984
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Yutaka Nakahara, Ryoji Kimura
  • Patent number: 4482561
    Abstract: The N-substituted-4-(optionally substituted)-2-, 3- or 4-piperidyl N-(7- or 8-substituted-4-quinolyl)-anthraniloyloxyalkanoates having the structural formula (I): ##STR1## in which R is a straight or branched chain alkyl radical having from 1 to 4 carbon atoms; an alkenyl or alkynyl radical having from 2 to 6 carbon atoms; a benzyl, phenethyl, 4-nitrophenethyl or 4-aminophenethyl radical; or a phenacyl, benzoylethyl, .beta.-hydroxyphenethyl or .alpha.-hydroxyphenylpropyl radical, optionally substituted on the phenyl ring by one or more halogen atom, trifluoromethyl, nitro or amino substituents, or an alkyl substituent having from 1 to 4 carbon atoms or an alkoxy substituent having from 1 to 4 carbon atoms; R.sub.1 is a hydrogen atom or a phenyl radical; each of R.sub.2 and R.sub.3 is independently a hydrogen atom or an alkyl radical having from 1 to 4 carbon atoms; one of R.sub.4 and R.sub.5 is a chlorine atom or a trifluoromethyl radical and the other of R.sub.4 and R.sub.
    Type: Grant
    Filed: November 12, 1982
    Date of Patent: November 13, 1984
    Assignee: Recordati, S. A., Chemical & Pharmaceutical Co.
    Inventors: Dante Nardi, Gianni Motta, Rodolfo Testa, Gabriele Graziani
  • Patent number: 4479002
    Abstract: Carbamate-carbamoyl fluoride compounds are useful intermediates for the production of insecticidal bis-carbamate compounds.
    Type: Grant
    Filed: December 1, 1975
    Date of Patent: October 23, 1984
    Assignee: Union Carbide Corporation
    Inventor: Wei C. Liang
  • Patent number: 4468403
    Abstract: Pharmaceutical compounds of the general formula (1) have been prepared ##STR1## and non-toxic pharmaceutically acceptable salts thereof, wherein R.sub.1 is a lower alkyl, phenyl lower alkyl, amino substituted phenyl lower alkyl, nitro substituted phenyl lower alkyl, cycloalkyl lower alkyl or a lower alkenyl substituent, R.sub.2 is a member selected from the group consisting of a cyano, pyridylsulfonyl, lower alkyl substituted sulfonyl, phenylsulfonyl, lower alkyl substituted phenylsulfonyl, lower alkoxy substituted phenylsulfonyl, halogen substituted phenylsulfonyl, nitro substituted phenylsulfonyl, amino substituted phenylsulfonyl and lower alkyl amido substituted phenylsulfonyl; R.sub.3 is a hydrogen or halogen atom; and R.sub.4 is a hydrogen, lower alkyl or lower alkoxy substituent, lower denoting a straight or branched chain having from 1-4 carbon atoms. These compounds exhibit analgesic agonist activity or analgesic agonist-antagonist activities.
    Type: Grant
    Filed: July 20, 1982
    Date of Patent: August 28, 1984
    Assignee: Canadian Patents & Development Limited
    Inventors: Edward E. Knaus, Brent K. Warren, Theodore A. Ondrus
  • Patent number: 4465834
    Abstract: A class of anticholinergic drugs having the formula ##STR1## in which R.sup.1 is a carbocyclic or branched aliphatic group of 3 to 8 carbon atoms, R.sup.2 is a branched or linear aliphatic group containing 3 to 10 carbon atoms with 1 to 2 olefinic or acetylenic bonds and R.sup.3 is an alkyl or cyclic group of 4 to 12 carbon atoms containing a tertiary amino nitrogen, are described.
    Type: Grant
    Filed: September 20, 1965
    Date of Patent: August 14, 1984
    Assignee: FMC Corporation
    Inventors: Burton M. Baum, Hugo Stange
  • Patent number: 4461898
    Abstract: Mixtures of esters of polyalkylpiperidine derivatives, of the formulae I and II ##STR1## in which the proportions of I to II are 95 to 70% by weight and 5 to 30% by weight, are obtained by reacting about 2 mols of a piperidine of the formula III ##STR2## with 0.9 to 1.3 mols of a diester of the formula IV ##STR3## in the melt at between 100.degree. and 145.degree. C., in the presence of an alkali metal amide as a catalyst.The mixtures of esters thus obtained are very suitable as light stabilizers for plastics.
    Type: Grant
    Filed: November 1, 1982
    Date of Patent: July 24, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Anton Meier, Eduard Troxler
  • Patent number: 4440887
    Abstract: Compounds of formula I ##STR1## where R.sub.1, R.sub.2 and R.sub.3 are defined in the text, are useful as light stabilizers for polymeric materials, particularly for thermoplastic polymers and automotive finishes. Preferred compounds are those in which R.sub.1 is hydrogen and R.sub.2 and R.sub.3 are identical (C.sub.8-17 alkyl)carbonyl groups.
    Type: Grant
    Filed: January 22, 1982
    Date of Patent: April 3, 1984
    Assignee: Sandoz Ltd.
    Inventors: Hans Hinsken, Wolfgang Mueller, Hermann Schneider