Chalcogen Bonded Directly To Ring Carbon Of The Piperidine Ring Patents (Class 546/242)
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Patent number: 4976889Abstract: 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: GrantFiled: November 14, 1988Date of Patent: December 11, 1990Assignee: BASF AktiengesellschaftInventors: Alexander Aumueller, Peter Neumann, Hubert Trauth
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Patent number: 4972009Abstract: 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: GrantFiled: August 18, 1989Date of Patent: November 20, 1990Assignee: Ciba-Geigy CorporationInventors: Joseph Suhadolnik, Ramanathan Ravichandran
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Patent number: 4970307Abstract: 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: GrantFiled: August 13, 1987Date of Patent: November 13, 1990Assignee: Fuji Photo Film Co., Ltd.Inventors: Keiji Takeda, Jiro Tsukahara, Kozo Sato
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Patent number: 4942238Abstract: 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: GrantFiled: May 22, 1989Date of Patent: July 17, 1990Assignee: Ciba-Geigy CorporationInventors: Gerhard Rytz, Mario Slongo
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Patent number: 4940795Abstract: 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: GrantFiled: October 5, 1988Date of Patent: July 10, 1990Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Shin-ichi Tsukamoto, Hitoshi Nagaoka, Shinji Usuda, Masatomi Harada, Toshinari Tamura
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N-substituted derivatives of 1-desoxynojirimycin and 1-desoxymannonojirimycin and pharmaceutical use
Patent number: 4940705Abstract: 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: GrantFiled: October 26, 1988Date of Patent: July 10, 1990Assignee: Bayer AktiengesellschaftInventors: Horst Boshagen, Bodo Junge, Arnold Paessens, Matthias Schuller -
Patent number: 4931562Abstract: 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: GrantFiled: January 11, 1989Date of Patent: June 5, 1990Assignees: Lion Corporation, Sankyo Company LimitedInventors: Yasuhiro Akabane, Takamitsu Tamura, Masami Fujiwara
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Patent number: 4910310Abstract: 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: GrantFiled: October 3, 1988Date of Patent: March 20, 1990Assignee: G. D. Searle & Co.Inventors: Arthur L. Campbell, James R. Behling, Kevin A. Babiak, John S. Ng, Richard A. Mueller, George W. J. Fleet
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Patent number: 4889953Abstract: 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: GrantFiled: July 22, 1987Date of Patent: December 26, 1989Assignee: Takeda Chemical Industries, Ltd.Inventors: Keizo Inoue, Hiroaki Nomura, Tetsuya Okutani
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Patent number: 4873329Abstract: 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: GrantFiled: February 21, 1985Date of Patent: October 10, 1989Assignee: Imperial Chemical Industries PLCInventors: Leslie R. Hughes, John Oldfield, Howard Tucker
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Patent number: 4871747Abstract: 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: GrantFiled: December 3, 1986Date of Patent: October 3, 1989Assignee: Bayer AktiengesellschaftInventors: Gunther Kinast, Matthias Schuller, Theo Schroder
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Patent number: 4831134Abstract: 1-Hydroxy-2,2,6,6,-tetraalkylpiperidine derivatives are effective as light stabilizers in a variety of substrate systems.Type: GrantFiled: September 21, 1987Date of Patent: May 16, 1989Assignee: Ciba-Geigy CorporationInventors: Ronald A. E. Winter, James P. Galbo
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Patent number: 4831146Abstract: 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: GrantFiled: March 21, 1988Date of Patent: May 16, 1989Assignee: Air Products and Chemicals, Inc.Inventors: Denise B. Taylor, Barton Milligan
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Patent number: 4824884Abstract: 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: GrantFiled: August 12, 1987Date of Patent: April 25, 1989Assignee: Pennwalt CorporationInventors: Ronald E. MacLeay, Robert T. Kazmierczak
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Patent number: 4820702Abstract: 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: GrantFiled: December 22, 1987Date of Patent: April 11, 1989Assignee: Riom Laboratories C.E.R.M.Inventors: Patrick Carlier, Jacques A. Simond, Andre J. Monteil
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Patent number: 4808582Abstract: 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: GrantFiled: March 19, 1987Date of Patent: February 28, 1989Assignee: Delalande S.A.Inventors: Alain Y. Platel, Guy R. Bourgery, Patrick G. Guerret
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Patent number: 4806650Abstract: 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: GrantFiled: April 2, 1987Date of Patent: February 21, 1989Assignee: Bayer AktiengesellschaftInventors: Theo Schroder, Mathias Stubbe
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Patent number: 4797486Abstract: 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: GrantFiled: October 14, 1987Date of Patent: January 10, 1989Assignee: Pfizer Inc.Inventors: Edward A. Glazer, James W. McFarland
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Patent number: 4774332Abstract: 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: GrantFiled: July 11, 1986Date of Patent: September 27, 1988Assignee: Sandoz, Ltd.Inventor: Lajos Avar
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Patent number: 4746655Abstract: 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: GrantFiled: June 10, 1987Date of Patent: May 24, 1988Assignee: A. H. Robins Company, IncorporatedInventor: Albert D. Cale, Jr.
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Patent number: 4735952Abstract: 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: GrantFiled: January 24, 1986Date of Patent: April 5, 1988Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Ikuo Ueda, Masaaki Matsuo, Kiyoshi Taniguchi, Takatomo Ogahara
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Patent number: 4734502Abstract: 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: GrantFiled: December 22, 1986Date of Patent: March 29, 1988Assignee: ICI Americas Inc.Inventors: Walter M. Kruse, John F. Stephen
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Patent number: 4731448Abstract: 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: GrantFiled: December 3, 1986Date of Patent: March 15, 1988Assignee: Ciba-Geigy CorporationInventors: Heinz Issler, Siegfried Kintopf, Lutz Konig, Hans Stephan
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Patent number: 4663459Abstract: 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: GrantFiled: February 14, 1985Date of Patent: May 5, 1987Assignee: Adeka Argus Chemical Co., Ltd.Inventors: Tohru Haruna, Atsushi Nishimura, Kazuo Sugibuchi
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Patent number: 4661597Abstract: 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: GrantFiled: February 14, 1985Date of Patent: April 28, 1987Assignee: Adeka Argus Chemical Co., Ltd.Inventors: Tohru Haruna, Atsushi Nishimura, Kazuo Sugibuchi
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Patent number: 4654433Abstract: 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: GrantFiled: January 14, 1985Date of Patent: March 31, 1987Assignee: Merck & Co., Inc.Inventor: David L. Hughes
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Patent number: 4649167Abstract: 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: GrantFiled: November 14, 1985Date of Patent: March 10, 1987Assignee: Pennwalt CorporationInventors: Ludwig K. Huber, James L. Reilly
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Patent number: 4639436Abstract: 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: GrantFiled: August 23, 1978Date of Patent: January 27, 1987Assignee: Bayer AktiengesellschaftInventors: Bodo Junge, Hans P. Krause, Lutz Muller, Walter Puls
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Patent number: 4638060Abstract: Antibacterial activity is exhibited by compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof.Type: GrantFiled: April 29, 1985Date of Patent: January 20, 1987Assignee: E. R. Squibb & Sons, Inc.Inventors: Joseph E. Sundeen, William H. Koster, Robert Zahler
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Patent number: 4621110Abstract: 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: GrantFiled: January 17, 1984Date of Patent: November 4, 1986Assignee: Montedison S.p.A.Inventor: Piero Di Battista
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Patent number: 4618634Abstract: 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: GrantFiled: February 27, 1985Date of Patent: October 21, 1986Assignee: Ciba-Geigy S.p.A.Inventors: Giuseppe Cantatore, Valerio Borzatta
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Patent number: 4614537Abstract: 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: GrantFiled: October 25, 1983Date of Patent: September 30, 1986Assignee: Bayer AktiengesellschaftInventors: Hans-Jochem Riebel, Ludwig Eue, Wilfried Faust, Uwe Priesnitz
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Patent number: 4611058Abstract: 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: GrantFiled: May 14, 1985Date of Patent: September 9, 1986Assignee: Bayer AktiengesellschaftInventor: Wolfgang Koebernick
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Patent number: 4548639Abstract: 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: GrantFiled: September 28, 1982Date of Patent: October 22, 1985Assignee: Bayer AktiengesellschaftInventors: Hans-Jochem Riebel, Ludwig Eue, Wilfried Faust, Uwe Priesnitz
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Patent number: 4537963Abstract: 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: GrantFiled: August 11, 1983Date of Patent: August 27, 1985Assignee: E. I. Du Pont de Nemours and CompanyInventor: Ashokkumar B. Shenvi
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Patent number: 4536581Abstract: 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: GrantFiled: May 18, 1983Date of Patent: August 20, 1985Assignee: Ciba-Geigy S.p.A.Inventors: Giuseppe Cantatore, Paolo Cassandrini
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Patent number: 4529760Abstract: 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: GrantFiled: November 1, 1983Date of Patent: July 16, 1985Assignee: Adeka Argus Chemical Co., Ltd.Inventors: William E. Leistner, Motonobu Minagawa, Yutaka Nakahara, Tohru Haruna, Atsushi Nishimura
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Patent number: 4522945Abstract: 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: GrantFiled: March 26, 1982Date of Patent: June 11, 1985Assignee: Janssen Pharmaceutica N.V.Inventors: Jan Vandenberk, Ludo Kennis, Marcel Van der Aa, Albert Van Heertum
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Patent number: 4515974Abstract: 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: GrantFiled: June 25, 1982Date of Patent: May 7, 1985Assignee: Bayer AktiengesellschaftInventors: Wilfried Zecher, Rudolf Merten
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Patent number: 4511722Abstract: 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: GrantFiled: February 16, 1983Date of Patent: April 16, 1985Assignee: Bayer AktiengesellschaftInventors: Heinrich Krimm, Hans-Josef Buysch, Peter M. Lange, Reinhold Klipper
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Patent number: 4500446Abstract: 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: GrantFiled: September 23, 1982Date of Patent: February 19, 1985Assignee: Chemicke zavody Juraja Dimitrova, narodny podnikInventors: Julius Durmis, Alojz Balogh, Milan Karvas, Maria Hrachovcova, Jan Masek, Pavol Caucik, Marta Povazancova
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Patent number: 4499273Abstract: 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: GrantFiled: December 21, 1982Date of Patent: February 12, 1985Inventors: Alberto Fontana, Renzo Fontanelli, Egeo Sacrini, Osvaldo Cicchetti
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Patent number: 4496732Abstract: 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: GrantFiled: March 14, 1983Date of Patent: January 29, 1985Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: George E. Lee, Thomas B. K. Lee
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Patent number: 4487887Abstract: 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: GrantFiled: September 9, 1983Date of Patent: December 11, 1984Assignee: Adeka Argus Chemical Co., Ltd.Inventors: Yutaka Nakahara, Ryoji Kimura
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Patent number: 4482561Abstract: 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: GrantFiled: November 12, 1982Date of Patent: November 13, 1984Assignee: Recordati, S. A., Chemical & Pharmaceutical Co.Inventors: Dante Nardi, Gianni Motta, Rodolfo Testa, Gabriele Graziani
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Patent number: 4479002Abstract: Carbamate-carbamoyl fluoride compounds are useful intermediates for the production of insecticidal bis-carbamate compounds.Type: GrantFiled: December 1, 1975Date of Patent: October 23, 1984Assignee: Union Carbide CorporationInventor: Wei C. Liang
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Patent number: 4468403Abstract: 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: GrantFiled: July 20, 1982Date of Patent: August 28, 1984Assignee: Canadian Patents & Development LimitedInventors: Edward E. Knaus, Brent K. Warren, Theodore A. Ondrus
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Patent number: 4465834Abstract: 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: GrantFiled: September 20, 1965Date of Patent: August 14, 1984Assignee: FMC CorporationInventors: Burton M. Baum, Hugo Stange
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Patent number: 4461898Abstract: 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: GrantFiled: November 1, 1982Date of Patent: July 24, 1984Assignee: Ciba-Geigy CorporationInventors: Anton Meier, Eduard Troxler
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Patent number: 4440887Abstract: 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: GrantFiled: January 22, 1982Date of Patent: April 3, 1984Assignee: Sandoz Ltd.Inventors: Hans Hinsken, Wolfgang Mueller, Hermann Schneider