Having -c(=x)-, Wherein X Is Chalcogen, Attached Indirectly To A Piperdine Ring By Nonionic Bonding Patents (Class 546/190)
  • Patent number: 4537960
    Abstract: N- and O-substituted carbamates are prepared by reacting urea with an aminopropanol at 140.degree. C. or above. The compounds obtained by the novel process are useful starting materials for the preparation of textile finishing agents, stabilizers, plasticizers, dyes and crop protection agents.
    Type: Grant
    Filed: September 2, 1983
    Date of Patent: August 27, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Gerhard Nestler, Friedrich Towae
  • Patent number: 4533499
    Abstract: A process for the production of a compound of formula ##STR1## which comprises reacting a compound of formula ##STR2## or a mixture of the compounds (2a) and (2b) with a compound ZH or a compound of formula ##STR3## or a mixture of the compounds (2c) and (2d) with a compound YH, both reactions under acidic conditions, wherein X and Y are the same or different and each represents an aromatic carbocyclic radical having an unsubstituted or substituted amino group in the para position to the indicated bond, or a heterocyclic group, and Z represents an aryl radical of formula ##STR4## wherein R.sub.1 and R.sub.2 independently of one another represent hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.2 -C.sub.8 -alkoxyalkyl, cycloalkyl, aralkyl, aryl, or substituted alkyl, cycloalkyl, aralkyl or aryl, or R.sub.1 and R.sub.
    Type: Grant
    Filed: April 6, 1984
    Date of Patent: August 6, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: Malcolm C. Clark, John B. Henshall, Derrick A. Hart
  • Patent number: 4532348
    Abstract: 1-(Substituted phenylthiocarbamyl) 3,3-disubstituted formamidine compounds having the structural formula ##STR1## wherein n is 1, 2 or 3,R is alkyl having 1 to 6 carbon atoms, alkoxy having 1 to 6 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogen, nitro, acyl having 1 to 4 carbon atoms, hydroxyl and ##STR2## wherein R.sup.3 and R.sup.4 have the same meaning as R.sup.1 and R.sup.2 defined below,R.sup.1 and R.sup.2 are the same or different and are alkyl having 1 to 6 carbon atoms, or taken together represent the chain --(CH.sub.2).sub.p --(X).sub.m --(CH.sub.2).sub.q and forming a ring structure with the nitrogen to which they are bound wherein p is 1, 2 or 3, q is 2 or 3, X represents --O--, --S--, --SO--, --SO.sub.2 --, --NR.sup.3 --, R.sup.3 is hydrogen or alkyl having 1 to 6 carbon atoms, and m is 0 or 1 and their use as pharmaceutical agents.
    Type: Grant
    Filed: July 16, 1980
    Date of Patent: July 30, 1985
    Assignee: Stauffer Chemical Company
    Inventors: Ferenc M. Pallos, Jack R. DeBaun, Eugene G. Teach
  • 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: 4526891
    Abstract: This invention relates to compounds of the formula: ##STR1## where X is hydrogen, halogen, lower alkoxy, lower alkyl, nitro, hydroxyl and CF.sub.3 ; R is H, and lower alkyl, R.sub.1 is CH.sub.3 SO.sub.3 and ##STR2## where R.sub.2 and R.sub.3 are the same or different and are hydrogen, lower alkyl, mesyl (CH.sub.3 SO.sub.
    Type: Grant
    Filed: March 10, 1983
    Date of Patent: July 2, 1985
    Assignee: Hoechst Roussel Pharmaceuticals Inc.
    Inventors: Lawrence L. Martin, Linda L. Setescak
  • Patent number: 4500662
    Abstract: Polysubstituted .alpha.-aminoacetamides of the formula ##STR1## wherein R.sup.1 is tert-alkyl; R.sup.4 is alkyl, phenyl, substituted phenyl, cycloalkyl, piperidinyl, tetraalkylpiperidinyl or an alkylene (.alpha.-aminoacetamide). These compounds are prepared by first reacting an .alpha.-haloacetamide with a base to form an .alpha.-lactam intermediate which in turn is reacted with a primary amine. The compounds are useful as stabilizers of polymeric materials against ultraviolet light degradation.
    Type: Grant
    Filed: September 29, 1982
    Date of Patent: February 19, 1985
    Assignee: The B. F. Goodrich Company
    Inventor: John T. Lai
  • Patent number: 4499220
    Abstract: Copolymer light stabilizers are provided having at least one 2,2,6,6-tetraalkyl piperidyl group in the molecule and a molecular weight within the range from about 1000 to about 20,000, that are copolymers of a maleic or fumaric acid ester containing a 2,2,6,6-tetraalkyl piperidyl group in the alcohol group of the formula: ##STR1## wherein ##STR2## R.sub.2 is alkyl or R.sub.1 ; X is ##STR3## R.sub.6 is lower alkyl; R.sub.3 is hydrogen or alkyl;R.sub.4 is hydrogen or methyl;R.sub.5 is alkylene;Y is ##STR4## R.sub.7 is alkylene; and at least one monomer selected from the group consisting of aliphatic carboxylic acid vinyl ester having from two to eight carbon atoms; alkyl vinyl ethers having from one to eighteen carbon atoms; triallyl isocyanurate; pinene; and tricyclo-(5.2.1.0.sup.2.6)-decene-3; and synthetic resin compositions having improved light stability comprising per 100 parts by weight of resin from 0.001 to 5 parts by weight of the polymeric light stabilizer.
    Type: Grant
    Filed: May 20, 1982
    Date of Patent: February 12, 1985
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Motonobu Minagawa, Naohiro Kubota, Toshihiro Shibata
  • Patent number: 4489008
    Abstract: Hydrolytically stable hydroxyl-terminated liquid polymers that are useful in the preparation of polyurethanes prepared by reacting at least one aminoalcohol with a carboxyl-terminated liquid polymer having a carbon-carbon backbone. The hydroxyl-terminated polymers have the formula ##STR1## wherein B is a carbon-carbon backbone, X is HO-- or HO--Y-- a univalent radical obtained by removing a hydrogen atom from an amine group of aminoalcohol containing one primary or secondary hydroxyl group and one primary or secondary amine group per molecule, and the polymers contain an average of greater than 1.5 terminal hydroxyl groups per molecule.
    Type: Grant
    Filed: August 9, 1982
    Date of Patent: December 18, 1984
    Assignee: The B. F. Goodrich Company
    Inventor: Changkiu K. Riew
  • Patent number: 4486428
    Abstract: Bicyclic fused benzenoid compounds of the formula ##STR1## and pharmaceutically acceptable cationic and acid addition salts thereof, where M is O, CH.sub.2 or NR.sub.6 ; R.sub.6 is hydrogen, formyl, carbobenzyloxy or certain carboalkoxyalkyl, alkanoyl, alkyl, aralkyl or aralkylcarbonyl groups;A' is:(1) A where one of A and B is hydrogen such that when A is hydrogen, B is C(R.sub.2 R.sub.3)(CH.sub.2).sub.f Q and f is 1 or 2; when B is hydrogen, A is C(R.sub.2 R.sub.3)(CH.sub.2).sub.f Q and f is 0 or 1, when taken together A and OR.sub.1 form a lactone or certain derivatives thereof;(2) A' is ##STR2## (3) A' is Q.sub.3 ; Q is CO.sub.2 R.sub.7, COR.sub.8, C(OH)R.sub.8 R.sub.9, CN, CONR.sub.12 R.sub.13, CH.sub.2 NR.sub.12 R.sub.13, CH.sub.2 NHCOR.sub.14, CH.sub.2 NHSO.sub.2 R.sub.17 or 5-tetrazoyl;Q.sub.3 is ##STR3## 5-tetrazolyl, CH.sub.2 CONHCOR.sub.7, COOH or certain ester, amide, carboximido or sulfonimido derivatives thereof, CONHOH, CONHCONH.sub.2, or COCH.sub.2 Q.sub.4 where Q.sub.
    Type: Grant
    Filed: January 13, 1983
    Date of Patent: December 4, 1984
    Assignee: Pfizer Inc.
    Inventors: James F. Eggler, Michael R. Johnson, Lawrence S. Melvin, Jr.
  • Patent number: 4481148
    Abstract: Hydroxyl-containing liquid polymers having an aliphatic polymeric backbone and sulfide linkages near the terminal portions of the polymer molecule are prepared by polymerizing (1) at least one of selected vinylidene monomers having at least one terminal CH.sub.2 .dbd.C< group per monomer molecule, together with (2) at least one hydroxyl-containing disulfide in the presence of (3) ultraviolet radiation.
    Type: Grant
    Filed: March 16, 1981
    Date of Patent: November 6, 1984
    Assignee: The B. F. Goodrich Company
    Inventor: Changkiu K. Riew
  • Patent number: 4481315
    Abstract: Compounds which contain, in their molecule, at least one 2-(2'-hydroxyphenyl)-benztriazole group or one 2-hydroxybenzophenone group and at least one polyalkylpiperidine group are effective light stabilizers for organic materials, in particular for polymers. The use of the compounds as light stabilizers for lacquers is of particular importance.
    Type: Grant
    Filed: February 28, 1983
    Date of Patent: November 6, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Jean Rody, Mario Slongo
  • Patent number: 4479950
    Abstract: Compounds of the structure ##STR1## wherein: P and Q are independently hydrogen, halo, CF.sub.3, OR.sub.1, SR.sub.1, sulfamoyl, alkyl and NR.sub.1 R.sub.2 ;R.sub.1, and R.sub.2 are independently hydrogen, alkyl, aminoalky, aryl, aralkyl, heteroaryl or cycloalkyl;Y is OH, OR.sub.1, NH.sub.2, or, N(R.sub.1 R.sub.2); andM is alkyl, cycloalkyl, aryl, aminoalkyl, aralkyl, heteroaryl or heterocyclicwherein:the alkyl groups and the alkyl moieties of aminoalkyl, alkoxy and thioalkyl contain from 1 to 6 carbon atoms; the cycloalkyl group contains from 3 to 8 carbon atoms; the aryl group contains from 6 to 10 carbon atoms; the aralkyl group contains from 7 to 16 carbon atoms; and the hetero group is selected from pyrrolidyl, piperidinyl, morpholinyl, pyridyl, quinolinyl, furyl, furfuryl and thienyl; and where Y is a hydroxy, their pharmaceutically acceptable, non-toxic alkali, alkaline earth and amine salts, have angiotensin converting enzyme inhibitory activity.
    Type: Grant
    Filed: November 5, 1982
    Date of Patent: October 30, 1984
    Assignee: USV Pharmaceutical Corporation
    Inventors: Paul R. Menard, Howard Jones, John T. Suh
  • Patent number: 4477616
    Abstract: Tetra-2,2,6,6-tetramethyl-4-piperidinyl)-3-methyl-5-(1',2'-biscarboxylate)- ethyl-cyclohexane or 3-cyclohexene-1,2-dicarboxylates are provided having the formula (I) or (II): ##STR1## wherein: R.sub.1 is selected from the group consisting of hydrogen, --O, alkyl, hydroxy alkyl and epoxyalkyl having from one to about eighteen carbon atoms, acyl having from one to about eighteen carbon atoms, cycloalkyl having from three to about eighteen carbon atoms; phenyl; phenalkyl and alkylphenyl having from seven to about twenty-four carbon atoms;R.sub.2 is lower alkyl having from one to about six carbon atoms; andX is selected from the group consisting of: ##STR2## as well as stabilized synthetic resin compositions comprising such piperidinyl compounds.
    Type: Grant
    Filed: March 3, 1983
    Date of Patent: October 16, 1984
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Motonobu Minagawa, Yutaka Nakahara, Toshihiro Shibata
  • Patent number: 4473694
    Abstract: Process for the synthesis of hindered polysubstituted .alpha.-amino acetamides which comprises first reacting an .alpha.-haloacetamide with a base to form an intermediate .alpha.-lactam which in turn is reacted with a primary or secondary amine. The product thus obtained can comprise a multifunctional compound having one or more hindered amino moieties. These compounds are highly effective as UV stabilizers in a variety of plastics, especially the alpha monoolefins.
    Type: Grant
    Filed: September 29, 1982
    Date of Patent: September 25, 1984
    Assignee: The B. F. Goodrich Company
    Inventor: John T. Lai
  • Patent number: 4468488
    Abstract: Poly(piperidylamine) alkanes represented by the Formula (I) or (II): ##STR1## and synthetic resin compositions having improved resistance to deterioration by light containing such compounds.
    Type: Grant
    Filed: February 28, 1983
    Date of Patent: August 28, 1984
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Motonobu Minagawa, Yutaka Nakahara, Toshihiro Shibata, Ryozo Arata
  • Patent number: 4468352
    Abstract: The distyrylbiphenyls of the formula ##STR1## in which X and X' independently of one another are a direct bond, oxygen, sulfur, --O--C.sub.1-3 -alkylene-CON(R.sub.4)----CON(R.sub.4)--, --O--C.sub.1-3 -alkylene-COO--, OCO or --COO--, with the proviso that if n+n'=O, X and Y' may not be --CON(R.sub.4)-- or O--C.sub.1-3 -alkylene-CON(R.sub.4)--, and if n+n'=2 and X and X' are --CON(R.sub.4)-- or --COO--, A.sup..crclbar. may not be a phosphite or phosphonate anion, and Y and Y' independently of one another are C.sub.1-20 -alkylene, R.sub.1 and R.sub.1 ' independently of one another are unsubstituted or substituted C.sub.1-8 -alkyl or C.sub.3-4 -alkenyl, or R.sub.1 together with R.sub.2, or R.sub.1 ' together with R.sub.2 ', is a heterocyclic ring, R.sub.2 and R.sub.2 ' independently of one another are unsubstituted or substituted C.sub.1-8 -alkyl or C.sub.3-4 -alkenyl, or R.sub.2 together with R.sub.1, or R.sub.2 ' together with R.sub.1 ', is a heterocyclic ring, or R.sub.1 and R.sub.2, or R.sub.1 ' and R.sub.
    Type: Grant
    Filed: April 28, 1982
    Date of Patent: August 28, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Christian Luthi, Hans R. Meyer, Kurt Weber
  • Patent number: 4463001
    Abstract: The present invention relates to new 6-substituted 6H-dibenzo [b,d]pyran derivatives, to a process for their preparation and pharmaceutical and veterinary compositions containing them.
    Type: Grant
    Filed: October 1, 1981
    Date of Patent: July 31, 1984
    Assignee: Farmitalia Carlo Erba S.p.A.
    Inventors: Piero Melloni, Paolo Salvadori, Pier P. Lovisolo
  • Patent number: 4463168
    Abstract: The instant invention relates to a process for the formation of polylactone polymers which are terminated on one end by a tertiary amine group, and on the other end by a hydroxyl group. An .epsilon.-caprolactone is reacted with an aromatic organic amine in the presence of a catalyst.
    Type: Grant
    Filed: December 23, 1983
    Date of Patent: July 31, 1984
    Assignee: Exxon Research and Engineering Co.
    Inventor: Robert D. Lundberg
  • Patent number: 4460725
    Abstract: Polyethers containing 2,2,6,6-tetramethyl piperidinyl carboxylic acid ester or ether groups are provided, comprising polymeric units having the structure ##STR1## wherein X is selected from the group consisting of: ##STR2## R.sub.1 is selected from the group consisting of hydrogen, --O, alkyl, hydroxy alkyl and epoxyalkyl having from one to about eighteen carbon atoms, acyl having from one to about eighteen carbon atoms, cycloalkyl having from three to about eighteen carbon atoms; phenyl; phenalkyl and alkylphenyl having from seven to about twenty-four carbon atoms;R.sub.2 is hydrogen or hydroxy;n.sub.1 is 0 or 1;R.sub.3 is lower alkyl having from one to about six carbon atoms; andn is the average number of such units in the polymer; as well as stabilized synthetic resin compositions comprising such polyethers.
    Type: Grant
    Filed: March 7, 1983
    Date of Patent: July 17, 1984
    Inventors: William E. Leistner, Motonobu Minagawa, Naohiro Kubota, Toshihiro Shibata, Ryozo Arata
  • Patent number: 4447428
    Abstract: Prostanoid compounds are described having the formula: ##STR1## where A is a cyclopentane ring, which is substituted by oxo and/or hydroxy or etherified hydroxy and may be saturated or unsaturated; X is --CH.dbd.CH--or --(CH.sub.2).sub.2 --; R is alkyl having a terminal --COOH or ester group; and Y is amino or substituted amino, particularly heterocyclic amino.The compounds have bronchodilator activity and/or inhibit blood platelet aggregation.The preparation and pharmaceutical formulation of the compounds is also described.
    Type: Grant
    Filed: July 15, 1983
    Date of Patent: May 8, 1984
    Assignee: Glaxo Group Limited
    Inventors: Eric W. Collington, Harry Finch, Roger F. Newton
  • Patent number: 4444928
    Abstract: Polymers or oligometic compounds of the general formula ##STR1## in which X, X.sup.a and X.sup.b are an ester, amide or cyano group, Y, Y.sup.a and Y.sup.b are --O-- or --NR.sup.10 --, R.sup.1, R.sup.1a and R.sup.1b are a group which contains a polyalkylpiperidine radical, and R.sup.1a can also be alkyl, and R.sup.3, R.sup.3a and R.sup.3b are alkylene, alkenylene, arylene-dialkylene, cycloalkylene-dialkylene or monooxa-alkylene or polyoxa-alkylene, can be prepared by the polycondensation of malonic acid esters or amides or cyanoacetic acid esters or amides with difunctional compounds, preferably dihalogen compounds, in the presence of bases. The products obtained have a molecular weight of 800 to 20,000 and are outstanding light stabilizers for organic polymers.
    Type: Grant
    Filed: August 4, 1982
    Date of Patent: April 24, 1984
    Assignee: Ciba-Geigy Corporation
    Inventor: Friedrich Karrer
  • Patent number: 4439565
    Abstract: Oligomeric esteramides having recurring structural units of the formula ##STR1## where G is a hindered amine radical of formula I or II ##STR2## in which R.sup.1 is hydrogen or alkyl having 1 to 4 carbon atoms, R.sup.2 is hydrogen, alkyl having 1 to 12 carbon atoms, allyl, benzyl, acetyl, acryloyl or cyano, Z.sub.1 is a direct bond, --NHCH.sub.2 CH.sub.2 --, --NHCH.sub.2 CH.sub.2 CH.sub.2 -- or --OCH.sub.2 CH.sub.2 --, Z.sub.2 is ethylene or trimethylene, E is a divalent aliphatic, aromatic or alicyclic radical and L is unsubstituted or substituted alkylene, are useful light stabilizers for plastics.
    Type: Grant
    Filed: November 10, 1982
    Date of Patent: March 27, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Roland A. E. Winter, Roger F. Malherbe, Frank Tieh-Yin Fu
  • Patent number: 4438112
    Abstract: Prostanoids are described of the formulae ##STR1## (and the salts thereof) in which: X is cis or trans --CH.dbd.CH-- or CH.sub.2 CH.sub.2 --;R.sup.1 is C.sub.1-7 alkyl terminated by --COOR.sup.10 where R.sup.10 is H, C.sub.1-6 alkyl or aralkyl;Y is a saturated heterocyclic amino group; andR.sup.4 is aralkyl (in which the aryl portion is substituted by alkylthio, alkylsulphinyl, alkylsulphonyl, alkanoylamino, aroylamino, phenalkyl, aminosulphonyl, alkanoylaminosulphonyl, phenylsulphonyl, nitro, tetrazolyl, substituted phenyl or thienyl).These compounds inhibit blood platelet aggregation and have bronchodilatory action, and may be formulated for use as anti-asthmatics and antithrombotic agents.
    Type: Grant
    Filed: September 17, 1982
    Date of Patent: March 20, 1984
    Assignee: Glaxo Group Limited
    Inventors: Eric W. Collington, Peter Hallett, Christopher J. Wallis, John Bradshaw
  • Patent number: 4435334
    Abstract: Compounds which contain ammonium groups and sulphonic acid groups and which, in the betaine form, correspond to the formula ##STR1## wherein X denotes --CO-- or --SO.sub.2 --,R.sub.1 denotes hydrogen or alkyl,R.sub.2, R.sub.3 and R.sub.4, independently of one another denote alkyl, alkenyl or aralkyl, orR.sub.4 denotes ##STR2## Y denotes alkylene or xylylene, m denotes 1 or 2,n denotes 0 or 1, andR.sub.5 and R.sub.6, independently of one another, denote hydrogen, alkyl, alkoxy or halogen,and in addition, if n=1,R.sub.2 or R.sub.4 denotes amino, alkylamino, dialkylamino, aryl or cycloalkyl,R.sub.2 and R.sub.3, together with the nitrogen atom which is bonded to them, denote a 5-membered or 6-membered ring,R.sub.2, R.sub.3 and R.sub.4, together with the nitrogen atom which is bonded to them, denote a pyridinium ring, a group of the formula ##STR3## or hydrogen, Y denotes arylene, benzylene or a radical of the formula ##STR4## Z denotes a direct bond, --(CH.sub.2).sub.p --, --O--, --O--(CH.sub.2).sub.
    Type: Grant
    Filed: December 28, 1981
    Date of Patent: March 6, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Frank-Michael Stohr, Peter Wild, Horst Nickel
  • Patent number: 4423174
    Abstract: Synthetic resin compositions of improved resistance to deterioration by heat and light are provided containing a 2,2,6,6-tetramethyl piperidyl ether having the formula: ##STR1## The compounds of the invention can be prepared by the reaction of the 2,2,6,6-tetramethyl piperidyl alcohol R.sub.1 -OH with (poly) trimethylol alkane, (poly) pentaerthritol, or an alcohol containing an oxetane ring, to form the ether.The etherification is carried out by the conventional method, for example, by the reaction of R.sub.1 -OH with the organic sulfonate of the above-mentioned alcohols, or by the reaction of R.sub.1 -OH with the halogenated above-mentioned alcohols in the presence of an alkali or acid acceptor.The compounds where n is equal to 2 or more can be prepared by chain opening polymerization of the corresponding compound containing the oxetane ring.
    Type: Grant
    Filed: July 26, 1982
    Date of Patent: December 27, 1983
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Motonobu Minagawa, Naohiro Kubota, Ryoji Kimura
  • Patent number: 4419354
    Abstract: This disclosure describes certain substituted 9,10-bis(2-aminoethoxy)anthracenes which are useful as modulators of the immune response system in warm-blooded animals and for inducing the regression of tumors in such animals.
    Type: Grant
    Filed: June 3, 1982
    Date of Patent: December 6, 1983
    Assignee: American Cyanamid Company
    Inventors: Ralph G. Child, Stanley A. Lang, Jr.
  • Patent number: 4412021
    Abstract: Polyalkylpiperidyl-ureas of the formula I ##STR1## in which m is 1-4, X, R.sup.2 and R.sup.3 are monovalent substituents and R.sup.1 is a m-valent radical, can be prepared from the corresponding 4-aminopiperidines by reaction with carbamoyl chlorides. They are outstanding stabilizers for plastics, and especially for polyolefins, to protect them against degradation by the action of light.
    Type: Grant
    Filed: February 23, 1982
    Date of Patent: October 25, 1983
    Assignee: Ciba-Geigy Corporation
    Inventor: Friedrich Karrer
  • Patent number: 4409213
    Abstract: Prostanoid compounds are described having the formula: ##STR1## where A is a cyclopentane ring, which is substituted by oxo and/or hydroxy or etherified hydroxy and may be saturated or unsaturated; X is --CH.dbd.CH-- or --(CH.sub.2).sub.2 --; R is alkyl having a terminal --COOH or ester group; and Y is amino or substituted amino, particularly heterocyclic amino.The compounds have bronchodilator activity and/or inhibit blood platelet aggregation.The preparation and pharmaceutical formulation of the compounds is also described.
    Type: Grant
    Filed: November 10, 1982
    Date of Patent: October 11, 1983
    Assignee: Glaxo Group Limited
    Inventors: Eric W. Collington, Harry Finch, Roger F. Newton, Christopher J. Wallis
  • Patent number: 4405737
    Abstract: N-2-Hydroxypropyl piperidines are provided, as well as a process for preparing these compounds, having the formula: ##STR1## wherein X is selected from the group consisting of , ##STR2## wherein R.sub.1 is selected from the group consisting of hydrogen; alkyl; alkenyl; cycloalkyl; alkaryl; hydroxyalkyl; oxyalkyl; acyl and aroyl having from one to about eighteen carbon atoms;R.sub.2 and R.sub.3 are each selected from the group consisting of alkyl, alkenyl, cycloalkyl, alkaryl, hydroxyalkyl, oxyalkyl and haloalkyl having from one to about eighteen carbon atoms;R.sub.4, R.sub.5 and R.sub.6 each are selected from the group consisting of hydrogen, alkyl, alkenyl, cycloalkyl, alkaryl, hydroxyalkyl, oxyalkyl and haloalkyl having from one to about eighteen carbon atoms; and --CH.sub.2 --O--R.sub.1 ;n is 1 or 2; andY, when n is 1, is hydroxy or ##STR3## and when n is 2, is oxyoxygen.
    Type: Grant
    Filed: February 5, 1982
    Date of Patent: September 20, 1983
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Bunji Hirai, Naohiro Kubota, Kazuo Sugibuchi
  • Patent number: 4404301
    Abstract: Polymeric light stabilizers are provided having at least one 2,2,6,6-tetraalkyl piperidyl group in the molecule and a molecular weight within the range from about 1000 to about 20,000, that are polymers of an unsaturated carboxylic acid ester selected from the group consisting of unsaturated cycloaliphatic mono-, di, and tri-carboxylic acid esters having from seven to about thirty carbon atoms; unsaturated branched-chain aliphatic di- and tri-carboxylic acid esters having from four to about thirty carbon atoms; sorbic acid ester, 3,8-nonadienyl acid ester, oleic acid ester, linolenic acid ester and ricinoleic acid ester; or copolymers of at least one thereof with another copolymerizable unsaturated monomer; and synthetic resin compositions having improved light stability comprising per 100 parts by weight of resin from 0.001 to 10 parts by weight of the polymeric light stabilizer.
    Type: Grant
    Filed: April 22, 1982
    Date of Patent: September 13, 1983
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Naohiro Kubota, Toshihiro Shibata, Ryozo Arata
  • Patent number: 4395508
    Abstract: New polycondensates of alkyl-substituted piperidines are disclosed. These new polycondensates are useful for stabilizing thermoplastic polymers, in particular polyolefins, against sunlight, heat and oxidation.A process for producing the new polycondensates is also disclosed, as well as the polymeric compositions stabilized with said new polycondensates.
    Type: Grant
    Filed: July 29, 1981
    Date of Patent: July 26, 1983
    Assignee: Montedison S.p.A.
    Inventors: Giuseppe Nelli, Roberto Oriani
  • Patent number: 4377690
    Abstract: Novel ligands of the general formula wherein r is 1 or 2, and L is a piperidine which is substituted by at least one enolate group in the 1-position or 4-position and wherein the ring nitrogen is sterically hindered by alkyl substituents in the adjacent positions. These ligands are useful in preparing light stabilizers.
    Type: Grant
    Filed: June 8, 1981
    Date of Patent: March 22, 1983
    Assignee: Ciba-Geigy Corporation
    Inventor: Paul Moser
  • Patent number: 4371695
    Abstract: New N-alkyl-piperidine derivatives of hydroxy-benzyl-malonic acid are disclosed. These new compounds are useful for stabilizing thermoplastic polymers, in particular polyole fins, against sunlight, heat and oxidation.A process for producing the new compounds is also disclosed, as well as the use thereof as stabilizers of polymers and polymeric compositions.
    Type: Grant
    Filed: June 3, 1981
    Date of Patent: February 1, 1983
    Assignee: Montedison S.p.A.
    Inventors: Piero Di Battista, Francesco Gratani
  • Patent number: 4348524
    Abstract: Compounds of the formula I ##STR1## in which m is 0 or 1 and n is 1 or 2 and R, R.sup.1, R.sup.2, Z and X are as defined in claim 1, and also salts of these compounds, are valuable light stabilizers for organic materials, especially for polymers. The compounds of the formula I can be prepared from the corresponding 4-sec.-aminopiperidines by reaction with cyclic dicarboxylic acid anhydrides and appropriate further reactions.
    Type: Grant
    Filed: March 17, 1981
    Date of Patent: September 7, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Friedrich Karrer, Paul Moser
  • Patent number: 4342756
    Abstract: Compounds are described of the formula ##STR1## (and their salts and solvates) in which: X is cis or trans --CH.dbd.CH--;R.sup.1 is C.sub.1-7 alkyl terminated by --COOR.sup.3 where R.sup.3 is H, C.sub.1-6 alkyl or C.sub.7-10 aralkyl;Y is a saturated heterocyclic amino group having 5-8 ring members; andR.sup.2 is C.sub.2-4 alkanoyl, C.sub.3-6 alkenyl (optionally substituted), C.sub.1-12 alkyl, or substituted or unsubstituted phenylalkyl, biphenylalkyl or naphthylalkyl.These compounds inhibit blood platelet aggregation and bronchoconstriction and may be formulated for use as antithrombotic and anti-asthmatic agents.
    Type: Grant
    Filed: April 29, 1981
    Date of Patent: August 3, 1982
    Assignee: Glaxo Group Limited
    Inventors: Eric W. Collington, Peter Hallett, Christopher J. Wallis, John Bradshaw, Norman F. Hayes
  • Patent number: 4339576
    Abstract: 1-[(3- or 4-Benzoylphenyl)-lower-alkyl]-[(CH.sub.2).sub.n --N.dbd.B]-substituted-piperidines, useful as anti-asthmatic, anti-allergic, anti-cholinergic, bronchodilator and anti-inflammatory agents, are prepared by alkylation of an appropriate substituted piperidine with a (3- or 4-benzoylphenyl)-lower-alkyl halide or tosylate; by reaction of a 1-[2-(3- or 4-lithiophenyl)-lower-alkyl]-[(CH.sub.2).sub.n --N.dbd.B]-substituted-piperidine with benzonitrile and hydrolysis of the resulting benzimidoyl compound; or by reduction of a 1-[.alpha.-(3- or 4-benzoylphenyl)-lower-alkanoyl]-[(CH.sub.2).sub.n --N.dbd.B]-substituted-piperidine. The analogous carbinols are prepared by reduction, with an alkali metal borohydride, of the ketone.
    Type: Grant
    Filed: August 24, 1981
    Date of Patent: July 13, 1982
    Assignee: Sterling Drug Inc.
    Inventor: Bernard L. Zenitz
  • Patent number: 4332954
    Abstract: Cyclic sulfoperfluoroaliphaticcarboxylic acid anhydrides, amide derivatives thereof, a process for making the same, curable compositions containing cyclic sulfoperfluoroaliphaticcarboxylic acid anhydrides or amide derivatives thereof and cationically-sensitive monomers, and a process for using cyclic sulfoperfluoroaliphaticcarboxylic acid anhydrides or amide derivatives thereof as catalysts for the cure of cationically-sensitive monomers.
    Type: Grant
    Filed: January 30, 1981
    Date of Patent: June 1, 1982
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Robert J. Koshar
  • Patent number: 4323691
    Abstract: Described are compounds of the formula ##STR1## wherein ##STR2## wherein Z is hydrogen or loweralkyl, R.sub.5 and R.sub.6 may be the same or different and are hydrogen, loweralkyl or together are alkylene of 4 or 5 carbon atoms,R.sub.2 is hydrogen, halo, haloloweralkyl, loweralkyl, loweralkoxy, loweralkylthio or ##STR3## wherein R.sub.5 and R.sub.6 are previously defined, R.sub.3 is hydroxy, alkoxy, branched alkoxy, adamantyloxy, morpholino, amino or amino substituted by loweralkyl or alkylene of 4 or 5 carbon atoms,R.sub.4 is hydrogen or loweralkyl, andX.sub.1 and X.sub.2 are hydrogen, loweralkyl, halo or when substituted on adjacent carbon atoms of the benzene ring form a 1,3-butadienylene linkage, Y is oxygen or sulfur, and pharmaceutically acceptable salts thereof. The compounds are effective as diuretic agents in increasing urinary excretion.
    Type: Grant
    Filed: December 1, 1980
    Date of Patent: April 6, 1982
    Assignee: Abbott Laboratories
    Inventors: Carroll W. Ours, Cheuk M. Lee
  • Patent number: 4321373
    Abstract: This invention relates to 2-hydroxy-3-naphthoic acid amides of the general formula: ##STR1## wherein R.sub.1 is hydrogen, a substituted or unsubstituted alkyl, cycloalkyl, aralkyl, or aryl group, and R.sub.2 and R.sub.3 are identical or different and are hydrogen, a substituted or unsubstituted alkyl, cycloalkyl, aralkyl, or aryl group, or, together with the nitrogen atom to which they are attached, a substituted or unsubstituted heterocyclic group. The compounds are useful as coupling components for diazo printing.
    Type: Grant
    Filed: August 29, 1980
    Date of Patent: March 23, 1982
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Siegfried Scheler
  • Patent number: 4317819
    Abstract: The invention provides compounds of general formula ##STR1## and physiologically acceptable salts, hydrates and bioprecursors thereof, in whichY and Z, which may be the same or different, each represent oxygen, sulphur, .dbd.CHNO.sub.2 or .dbd.NR.sub.3 where R.sub.3 is hydrogen, nitro, cyano, lower alkyl, aryl, alkylsulphonyl or arylsulphonyl;p has a value from 2 to 12;R.sub.1 represents ##STR2## in which R.sub.4 and R.sub.5 which may be the same or different, each represent hydrogen, lower alkyl, cycloalkyl, lower alkenyl, aralkyl or lower alkyl interrupted by an oxygen atom or a group >N-R.sub.6 in which R.sub.6 represents hydrogen or lower alkyl, or R.sub.4 and R.sub.5 together with the nitrogen atom to which they are attached form a 5 to 7-membered saturated heterocyclic ring which may contain an additional oxygen atom or the group >NR.sub.
    Type: Grant
    Filed: December 5, 1980
    Date of Patent: March 2, 1982
    Assignee: Glaxo Group Limited
    Inventors: John W. Clitherow, Barry J. Price, John Bradshaw, Michael Martin-Smith
  • Patent number: 4317767
    Abstract: New N-alkyl-piperidine derivatives of hydroxy-benzyl-malonic acid are disclosed. These new compounds are useful for stabilizing thermoplastic polymers, in partcular polyole fins, against sunlight, heat and oxidation.A process for producing the new compounds is also disclosed, as well as the use thereof as stabilizers of polymers and polymeric compositions.
    Type: Grant
    Filed: January 30, 1980
    Date of Patent: March 2, 1982
    Assignee: Montedison S.p.A.
    Inventors: Piero Di Battista, Francesco Gratani
  • Patent number: 4316837
    Abstract: Polyalkylated 4-aminopiperidine derivatives having the formula: ##STR1## wherein R is a C.sub.1 -C.sub.19 alkyl group, a cycloalkyl group of from 5 to 7 carbon atoms, an unsubstituted aryl group, an aryl group substituted with one or more C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy groups, an aralkyl group having 7 or 8 carbon atoms, or ##STR2## where x is an integer from 0 to 4 inclusive and R' is C.sub.1 -C.sub.4 alkyl, which are useful as stabilizers for synthetic polymers are disclosed. Also disclosed are compositions stable to photo-deterioration comprising said polyalkylated 4-aminopiperidine derivatives and a synthetic polymer.
    Type: Grant
    Filed: September 10, 1980
    Date of Patent: February 23, 1982
    Assignee: Carstab Corporation
    Inventors: Kenneth R. Molt, Mary J. Zestermann
  • Patent number: 4316903
    Abstract: Compounds of the structure: ##STR1## where A is either ##STR2## where R.sub.1 to R.sub.4 are various substituents are active as antibacterials and antifungals.
    Type: Grant
    Filed: May 5, 1978
    Date of Patent: February 23, 1982
    Assignee: Merck & Co., Inc.
    Inventors: Nathaniel Grier, Richard A. Dybas, Bruce E. Witzel
  • Patent number: 4310668
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, benzyl, benzoyl, alkanoyl of 1 to 5 carbon atoms or --CO--(CH.sub.2).sub.p --NR'R" wherein p is 0 or an integer from 1 to 4; each of R' and R" when taken individually is hydrogen or alkyl of 1 to 4 carbon atoms; R' and R" when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring selected from piperidino, pyrrolo, pyrrolidino, morpholino and N-alkylpiperazino having from 1 to 4 carbon atoms in the alkyl group;R.sub.2 is selected from hydrogen, alkanoyl of 1 to 6 carbon atoms and benzoyl;R.sub.3 is selected from hydrogen, methyl and ethyl;R.sub.4 is selected from hydrogen, alkyl of 1 to 6 carbon atoms and benzyl;Z is selected from:(a) alkylene having from one to nine carbon atoms;(b) --(alk.sub.1).sub.m --X--(alk.sub.2).sub.n -- wherein each of (alk.sub.1) and (alk.sub.2) is alkylene having from 1 to 9 carbon atoms, with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.
    Type: Grant
    Filed: December 22, 1980
    Date of Patent: January 12, 1982
    Assignee: Pfizer Inc.
    Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
  • Patent number: 4310529
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, benzyl, benzoyl, alkanoyl of 1 to 5 carbon atoms or --CO--(CH.sub.2).sub.p --NR'R" wherein p is 0 or an integer from 1 to 4; each of R' and R" when taken individually is hydrogen or alkyl of 1 to 4 carbon atoms; R' and R" when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring selected from piperidino, pyrrolo, pyrrolidino, morpholino and N-alkylpiperazino having from 1 to 4 carbon atoms in the alkyl group;R.sub.2 is selected from hydrogen, alkanoyl of 1 to 6 carbon atoms and benzoyl;R.sub.3 is selected from hydrogen, methyl and ethyl;R.sub.4 is selected from hydrogen, alkyl of 1 to 6 carbon atoms and benzyl;Z is selected from:(a) alkylene having from one to nine carbon atoms;(b) --(alk.sub.1).sub.m --X--(alk.sub.2).sub.n --wherein each of (alk.sub.1) and (alk.sub.2) is alkylene having from 1 to 9 carbon atoms, with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.
    Type: Grant
    Filed: December 22, 1980
    Date of Patent: January 12, 1982
    Assignee: Pfizer Inc.
    Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
  • Patent number: 4289686
    Abstract: Compounds which contain, in their molecule, at least one 2-(2'-hydroxyphenyl)-benztriazole group or one 2-hydroxybenzophenone group and at least one polyalkylpiperidine group are effective light stabilizers for organic materials, in particular for polymers. The use of the compounds as light stabilizers for lacquers is of particular importance.
    Type: Grant
    Filed: September 17, 1979
    Date of Patent: September 15, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Jean Rody, Mario Slongo
  • Patent number: 4284829
    Abstract: Compounds useful for pharmacological and medicinal purposes having the formulae ##STR1## wherein R is H, C.sub.1 -C.sub.5 alkanoyl; R.sub.1 is H, benzyl, C.sub.1 14 C.sub.5 alkanoyl, P(O)(OH).sub.2, --CO(CH.sub.2).sub.2 COOH or a basic acyl group; each of R.sub.2 and R.sub.4 is H, C.sub.1 -C.sub.6 alkyl, phenyl, pyridyl or (CH.sub.2).sub.y C.sub.6 H.sub.5 ; y is 1-4; R.sub.3 is H or CH.sub.3 ; Z is C.sub.1 -C.sub.13 alkylene or --(alk.sub.1).sub.m --O--(alk.sub.2).sub.n --; each of (alk.sub.1) and (alk.sub.2) is C.sub.1 -C.sub.13 alkylene with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.2) is not greater than 13; each of m and n is 0 or 1; and W is H, pyridyl, phenyl, fluorophenyl or chlorophenyl; intermediates therefor and methods for their preparation and use.
    Type: Grant
    Filed: December 22, 1978
    Date of Patent: August 18, 1981
    Assignee: Pfizer Inc.
    Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
  • Patent number: 4271294
    Abstract: Compounds of the formula I ##STR1## wherein Ar.sup.1 and Ar.sup.2 represent unsubstituted or substituted phenyl, R.sup.1 represents hydrogen, alkyl, alkoxy, hydroxyalkyl, allyl, benzyl or a group --O--R.sup.2 -NR.sup.3 R.sup.4, R.sup.2 represents alkylene and --NR.sup.3 R.sup.4 is an open chain or cyclic organic amino group, are effective initiators for the photopolymerization of unsaturated compounds or for the photocrosslinking of polyolefins. They can be obtained by different methods which are in themselves known, in particular by reaction of the corresponding haloalkyl ethers or haloalkyl ketals with primary or secondary amines.
    Type: Grant
    Filed: March 13, 1980
    Date of Patent: June 2, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Louis Felder, Rudolf Kirchmayr, Rinaldo Kusler
  • Patent number: 4265803
    Abstract: The invention entitled "Polymers containing polyalkylpiperidines and use thereof as stabilizers" provides a class of polymers in which groups containing sterically hindered polyalkylpiperidines are linked in the main chain of the polymers via bridging members containing 2-hydroxy-1,3-trimethylene groups.The polymers show superior stabilizing effects for various synthetic polymers such as polyolefins against degradation thereof induced by light and/or heat. The polymers have advantages, as compared with known stabilizer compounds, that they hardly volatile upon processing with heating or during storage of articles containing thereof, and that they are resistant to extraction with solvents from articles containing thereof.
    Type: Grant
    Filed: August 7, 1978
    Date of Patent: May 5, 1981
    Assignee: Sankyo Company Limited
    Inventors: Nobuo Soma, Syoji Morimura, Takao Yoshioka, Tomoyuki Kurumada
  • Patent number: 4247694
    Abstract: The invention relates to metal salts of hydroxybenzoic acids which are complexed with a 4-amino-polyalkylpiperidine derivative or to mixed metal salts of a hydroxybenzoic acid and a polyalkylpiperidine carboxylic acid which may be complexed or not with an 4-amino-polyalkylpiperidine. The metal cation may be that of a di- or trivalent metal such as Ni, Co, Al, Zn or Ca. From hydroxybenzoic acids the 3,5-di-tert.butylbenzoic acid is preferred.These salts are valuable light stabilizers for plastics, especially for polyolefins, styrene polymers and polyamides or polyurethanes respectively. The salts show a strong tendency to retain water. For high compatibility with plastics a low water content is of importance.
    Type: Grant
    Filed: October 10, 1978
    Date of Patent: January 27, 1981
    Assignee: Ciba-Geigy Corporation
    Inventor: Michael Rasberger