Plural Chalcogens Bonded Directly To Ring Carbons Of The Piperidine Ring Patents (Class 514/328)
  • Patent number: 5378712
    Abstract: N-Acyl-.alpha.-aminocarboxylic acid derivatives of the formula ##STR1## wherein L, R' to R"' and Q have the significance given in the description, can be used for the treatment or control of illnesses which are caused by the binding of adhesive proteins to blood platelets and by blood platelet aggregation and cell-cell adhesion.
    Type: Grant
    Filed: March 19, 1992
    Date of Patent: January 3, 1995
    Assignee: Hoffmann-La Roche Inc
    Inventors: Leo Alig, Paul Hadvary, Marianne Hurzeler, Marcel Muller, Beat Steiner, Thomas Weller
  • Patent number: 5321031
    Abstract: Amides of the formula ##STR1## wherein: R.sup.1 is A and R.sup.2 is B; R.sup.1 is B and R.sup.2 is A; or R.sup.1 and R.sup.2 are independently selected from the group B;A is phenyl, substituted phenyl, heteroaryl, or substituted heteroaryl;B is cycloalkyl, substituted cycloalkyl, heterocycloalkyl, or substituted heterocycloalkyl;R.sup.3 is an alkyl chain of 1 to 25 carbon atoms, branched or straight; an alkenyl chain of 2 to 25 carbon atoms, branched or straight; a substituted alkyl chain; a substituted alkenyl chain; an interrupted alkyl chain; an interrupted alkenyl chain; a substituted interrupted alkyl chain; or a substituted interrupted alkenyl chain;R.sup.4 is hydrogen, lower alkyl, phenyl, Q-substituted phenyl, heteroaryl or Q-substituted heteroaryl;R.sup.6 and R.sup.7 are both H, or R.sup.6 and R.sup.7 together represent =O;or a pharmaceutically acceptable salt thereof;useful as inhibitors of acyl-coenzyme A:cholesterol acyl transferase and therefore in the treatment of atherosclerosis are disclosed.
    Type: Grant
    Filed: September 23, 1992
    Date of Patent: June 14, 1994
    Assignee: Schering Corporation
    Inventor: Sundeep Dugar
  • Patent number: 5310745
    Abstract: A method of inhibiting lentivirus is disclosed which comprises mammalian host susceptible to said lentivirus with a virally inhibitory effective amount of an O-acylated derivative of 1,5-dideoxy-1,5-imino-D-glucitol and their N-alkyl, N-acyl and N-aroyl derivatives in which from one to four of the free hydroxyl groups are O-acylated with carboxylic alkanoyl radicals selected from the group consisting of .omega.,.omega.,.omega.-trifluoroalkanoyl having from three to eight carbon atoms, carboxylic cycloalkanoyl groups having from four to eight carbon atoms and carboxylic acyclic alkanoyl groups having from two to ten carbon atoms, wherein the N-aroyl groups contain from 7 to 14 carbon atoms, the N-acyl groups contain from 4 to 8 carbon atoms and the N-alkyl groups contain from 1 to 14 carbon atoms.
    Type: Grant
    Filed: August 13, 1992
    Date of Patent: May 10, 1994
    Assignee: G. D. Searle & Co.
    Inventors: Richard A. Partis, Francis J. Koszyk, Richard A. Mueller
  • Patent number: 5300516
    Abstract: Musacarinic receptor antagonists, particularly useful in the treatment of irritable bowel syndrome, of formula (I), or a pharmaceutically acceptable salt thereof, where m is 1 or 2; R.sup.1 and R.sup.2 are each independently H or C.sub.1 -C.sub.4 alkyl or together represent --(CH.sub.2).sub.p -- where p is an integer of from 2 to 5; R.sup.3 is H or C.sub.1 -C.sub.4 alkyl; wherein Z is a direct link; --CH.sub.2 --, --CH.sub.2 O-- or --CH.sub.2 S--; and R.sup.4 is a group of formulae (II), (III), (IV) or Het, where R.sup.5 and R.sup.6 are each independently H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, --(CH.sub.2).sub.n OH, halo, trifluoromethyl, cyano, --(CH.sub.2).sub.n NR.sup.7 R.sup.8, --CO(C.sub.1 -C.sub.4 alkyl), --OCO(C.sub.1 -C.sub.4 alkyl), --CH(OH)(C.sub.1 -C.sub.4 alkyl), --C(OH)(C.sub.1 -C.sub.4 alkyl).sub.2, --SO.sub.2 NH.sub.2 , (CH.sub.2).sub.n CONR.sup.7 R.sup.8 or --(CH.sub.2).sub.n COO(C.sub.1 -C.sub.4 alkyl); R.sup.7 and R.sup.8 are each independently H or C.sub.1 -C.sub.
    Type: Grant
    Filed: June 11, 1992
    Date of Patent: April 5, 1994
    Assignee: Pfizer Inc.
    Inventors: Alexander R. Mackenzie, Peter E. Cross
  • Patent number: 5292750
    Abstract: Compounds are described which are useful for lowering the activity of .alpha..sub.2 -PI, for the treatment of myocardial infarctions and cerebral infarctions, as urokinase secretion accelerators, as antithrombotic agents and to accelerate the fibrinolysis accelerating effect.
    Type: Grant
    Filed: September 8, 1992
    Date of Patent: March 8, 1994
    Assignee: Nippon Shinyaku Co. Ltd.
    Inventors: Yoshiaki Yoshikuni, Nobutoshi Ojima, Kazuya Mori
  • Patent number: 5258518
    Abstract: 2-Substituted tertiary carbinol derivatives of deoxynojirimycin are disclosed having the formula ##STR1## wherein R.sub.4 =an alkyl, vinyl, alkenyl, alkynyl, aryl, aralkyl, alkenylalkyl, alkylnylalkyl or CH.sub.2 Y substituent having from about 1 to 10 carbon atoms;Y=OR', SR', NR'R', or N.sub.3 ;R=H or CH.sub.3 ; andR=H or an alkyl, aralkyl, alkenylalkyl, alkynylalkyl, aralkenyl, aralkynyl or hydroxyalkyl substituent, having from about 1 to 18 carbon atoms, provided that no carbon unsaturated bond is directly attached to nitrogen.These compounds have useful antiviral activity as demonstrated against lentivirus.
    Type: Grant
    Filed: April 1, 1992
    Date of Patent: November 2, 1993
    Assignee: G. D. Searle & Co.
    Inventors: Ish K. Khanna, Richard A. Mueller, Richard M. Weier
  • Patent number: 5250545
    Abstract: Sugar lactams such as N-(3-phenylpropyl)-1-deoxynojirimycin, 1-deoxynojirimycin, D-glucaro-.delta.-lactam, 6-O-triphenylmethyl-D-gluco-.delta.-lactam, etc., and new derivatives thereof which inhibit metastasis of cancer cells.
    Type: Grant
    Filed: December 3, 1990
    Date of Patent: October 5, 1993
    Assignee: Meiji Seika Kaisha, Ltd.
    Inventors: Tsutomu Tsuruoka, Satoru Nakabayashi, Harumi Fukuyasu, Yuuko Ishii, Takashi Tsuruoka, Haruo Yamamoto, Shigeharu Inouye, Shinichi Kondo
  • Patent number: 5238947
    Abstract: The present invention are novel compounds of the formula: ##STR1## wherein R is OH, NH.sub.2, OW, or H; X is H, F, Cl, Br, I, OH, OW, NO.sub.2 or NH.sub.2 ; Y is H, F, Cl, I, or Br; W is C(O)Z or a C.sub.1 to C.sub.12 alkyl group; Z is an aliphatic or aromatic group of from C.sub.1 to C.sub.12 ; X and Y can both vary within the molecule; and if R is H, at least one of X or Y is not H. In a preferred embodiment, R is OH or NH.sub.2. The most preferred compound is (4-hydroxy-3-N-phenylacetylamino-2,6-piperidinedione), in which R is OH, X is H and Y is H. These compounds have cytostatic activity and insert stereochemically into DNA.
    Type: Grant
    Filed: May 21, 1991
    Date of Patent: August 24, 1993
    Assignees: University of Georgia Research Foundation, Inc., Stereochemical Genetics, Inc.
    Inventors: Lawrence B. Hendry, Chung K. Chu, Virendra B. Mahesh
  • Patent number: 5206251
    Abstract: Novel derivatives of 1-deoxynojirimycin are disclosed which have amino or azido substituents at C-2 and/or C-3. These compounds are useful inhibitors of lentiviruses. Methods of chemical synthesis of these derivatives and intermediates therefor are also disclosed.
    Type: Grant
    Filed: April 1, 1992
    Date of Patent: April 27, 1993
    Assignee: G. D. Searle & Co.
    Inventors: Ish K. Khanna, Richard A. Mueller, Richard M. Weier
  • Patent number: 5198451
    Abstract: Novel N-substituted azaheterocyclic carboxylic acids and esters thereof in which a substituted alkyl chain forms part of the N-substituent, the compounds thus having the general formula I ##STR1## wherein Y is ##STR2## wherein R.sup.1 and R.sup.2 independently are C.sub.3-8 cycloalkyl phenyl or thienyl all of which may be optionally substituted with halogen, trifluoromethyl, C.sub.1-16 alkyl or C.sub.1-6 alkoxy;s is 1, 2 or 3;x is --CH.sub.2 --, --O-- or ##STR3## -wherein R.sup.3 is hydrogen or C.sub.1-6 -alkyl; r is 2, 3 or 4; R.sup.4 and R.sup.5 each represents hydrogen or may together represent a bond and R.sup.6 is OH or C.sub.1-8 -alkoxy; and pharmaceutically acceptable acid addition salts are potent inhibitors of GABA uptake from the synaptic cleft.
    Type: Grant
    Filed: November 20, 1990
    Date of Patent: March 30, 1993
    Assignee: Novo Nordisk A/S
    Inventors: Knud E. Andersen, Lars J. Stray Knudsen, Ursula Sonnewald, Per O. Sorensen
  • Patent number: 5192772
    Abstract: Compounds are described which are useful for lowering the activity of .alpha..sub.2 -PI, for the treatment of myocardial infarctions and cerebral infarctions, as urokinase secretion accelerators, as antithrombotic agents and to accelerate the fibrinolysis accelerating effect.
    Type: Grant
    Filed: August 12, 1991
    Date of Patent: March 9, 1993
    Assignee: Nippon Shinyaku Co. Ltd.
    Inventors: Yoshiaki Yoshikuni, Nobutoshi Ojima, Kazuya Mori
  • Patent number: 5177086
    Abstract: Phenyl-3-aminoalkyl-4-methyl-2,6-dioxopiperidines of the Formula I ##STR1## wherein: R.sub.1 represents hydrogen or C.sub.1 -C.sub.4 alkyl;n is 1 or 2;R.sub.2 represents hydrogen or methyl, provided that one R.sub.2 is hydrogen when n is 2;R.sub.3 represents hydrogen or C.sub.1 -C.sub.2 alkyl;R.sub.4 represents C.sub.1 -C.sub.2 alkyl;R.sub.5 and R.sub.6 independently represent hydrogen or methyl;m is 0 to 3; andeach Y is in a meta or para position and independently represents hydroxy, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 hydroxyalkyl, halogen, or trifluoromethyl, provided that hydroxy and alkoxy are not in the para position,and not pharmacologically acceptable salts thereof have memory enhancing activity and are particularly useful in the treatment of cognitive deficiencies such as senile dementia.The presently preferred compound is 3-(3'methoxyphenyl)-3-(3'-N,N-dimethylaminopropyl)-4,4-dimethyl-2,6-dioxop iperidine (AGN 2979).
    Type: Grant
    Filed: July 12, 1991
    Date of Patent: January 5, 1993
    Assignee: National Research Development Corporation
    Inventor: Brenda Costall
  • Patent number: 5137886
    Abstract: The invention provides insecticidally active compounds of formula (I): ##STR1## wherein X is nitrogen or carbon bearing a hydrogen atom; R.sup.1 is a group of formula --S(O).sub.n --Y, wherein Y is an optionally substituted heterocyclic ring containing at least one nitrogen atom, the point of attachment of the group Y being at a ring nitrogen atom, and n is 0, 1 or 2; R.sup.2 is a group of formula --OSO.sub.2 R.sup.3 wherein R.sup.3 is selected from C.sub.1-8 alkyl, C.sub.1-4 alkyl substituted by an optionally substituted phenyl or heterocyclic ring, C.sub.1-8 haloalkyl, C.sub.2-6 alkenyl, C.sub.2-4 alkenyl substituted by an optionally substituted phenyl or heterocyclic ring, C.sub.2-4 alkynyl, C.sub.2-4 alkynyl substituted by an optionally substituted phenyl or heterocyclic ring, optionally substituted aryl, and a group of formula --N(R.sup.4)(R.sup.5) wherein R.sup.4 and R.sup.5 are independently selected from hydrogen and C.sub.1-6 alkyl or wherein R.sup.4 and R.sup.5 together represent --(CH.sub.2).sub.
    Type: Grant
    Filed: December 6, 1990
    Date of Patent: August 11, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: Robin A. E. Carr, Donn W. Moseley, Nan C. Sillars
  • Patent number: 5128347
    Abstract: Novel compounds represented by the formula: ##STR1## wherein R represents hydrogen, alkyl radicals having from 1 to about 10 carbon atoms, alkenyl radicals having from 1 to about 10 carbon atoms, aryl, alkaryl and aralkyl radicals having from about 6 to about 16 carbon atoms and acyl and acyloxy radicals having from about 1 to about 10 carbon atoms, manifest glycosidase inhibition activity.
    Type: Grant
    Filed: October 18, 1990
    Date of Patent: July 7, 1992
    Assignee: Monsanto Company
    Inventors: Daniel P. Getman, Gary A. DeCrescenzo
  • Patent number: 5116622
    Abstract: The present invention provides methods for treating Parkinson's disease by administering to an afflicted host pharmaceutical compositions containing a therapeutically effective amount of urine peptide fractions containing 3-[N-phenylacetylaminopiperidine]-2,6-dion.
    Type: Grant
    Filed: September 12, 1990
    Date of Patent: May 26, 1992
    Inventor: Stanislaw R. Burzynski
  • Patent number: 5093342
    Abstract: Use of 5-methoxy-2[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]-sulfinyl]-1H-benz imidazole or a pharmaceutically acceptable salt thereof in the treatment of infectious diseases, especially such caused by Campylobacter pylori.
    Type: Grant
    Filed: September 12, 1990
    Date of Patent: March 3, 1992
    Assignee: Aktiebolaget Hassle
    Inventors: Masaaki Tomoi, Yoshifumi Ikeda, Yoshiko Yokota
  • Patent number: 5089508
    Abstract: The present invention provides methods for treating AIDS-related diseases by administering to an afflicted host pharmaceutical compositions containing a therapeutically effective amount of substituted piperidinedione of the formula ##STR1## or mixtues thereof, wherein R is OH, NH.sub.2, OW, or H;X is H, F. Cl, Bri, I, OH, OW, NO.sub.2, or NH.sub.2 ;Y is H, F. Cl, Bri, or I;W is ##STR2## or a C.sub.1 to C.sub.12 aliphatic group; Z is an aliphatic or aromatic group of C.sub.1 to C.sub.12 ;X and Y can both vary within the compound; and pharmaceutically acceptable salts thereof.The pharmaceutical compositions further may include R,X,Y substituted phenylacetic acid.
    Type: Grant
    Filed: September 4, 1990
    Date of Patent: February 18, 1992
    Inventor: Stanislaw R. Burzynski
  • Patent number: 5051407
    Abstract: A method for treating a viral infection in a human or animal patient comprising administering to such patient an antivirally effective amount of a substituted hydroxypiperidine, namely a 2-hydroxymethylene-3,4,5-trihydroxypiperidine.
    Type: Grant
    Filed: October 19, 1988
    Date of Patent: September 24, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Horst Boshagen, Bodo Junge, Gunther Kinast, Matthias Schuller, Jurgen Stoltefuss, Arnold Paessens
  • Patent number: 5047425
    Abstract: Compounds of the formula ##STR1## wherein Ar, R, R.sub.1, R.sub.2, R.sub.3, R.sub.4, X and n have the meanings mentioned in the description, processes and intermediates for their preparation, pharmaceutical compositions which contain them and their use in therapy in the treatment of cardiovascular diseases.
    Type: Grant
    Filed: November 30, 1988
    Date of Patent: September 10, 1991
    Assignee: Simes Societa Italiana Medicinali & Sintetici SpA
    Inventors: Cesare Casagrande, Francesco Santangelo, Luisa Calabi
  • Patent number: 5026713
    Abstract: Novel compounds represented by the formula: ##STR1## wherein R represents hydrogen, optionally substituted alkyl radicals having from 1 to about 10 carbon atoms, optionally substituted alkenyl radicals having from 1 to about 10 carbon atoms, optionally substituted aryl, alkaryl and aralkyl radicals having from about 6 to about 16 carbon atoms and optionally substituted acyl and acyloxy radicals having from about 1 to about 10 carbon atoms, manifest glycosidase inhibition activity.
    Type: Grant
    Filed: August 29, 1989
    Date of Patent: June 25, 1991
    Assignee: Monsanto Company
    Inventors: Daniel P. Getman, Gary A. DeCrescenzo
  • Patent number: 5025021
    Abstract: Novel compounds represented by the formula: ##STR1## wherein R represents hydrogen, optionally substituted alkyl radicals having from 1 to about 10 carbon atoms, optionally substituted alkenyl radicals having from 1 to about 10 carbon atoms, optionally substituted aryl, alkaryl and aralkyl radicals having from about 6 to about 16 carbon atoms and optionally substituted acyl and acyloxy radicals having from about 1 to about 10 carbon atoms, manifest glycosidase inhibition activity.
    Type: Grant
    Filed: July 27, 1989
    Date of Patent: June 18, 1991
    Assignee: Monsanto Company
    Inventors: Daniel P. Getman, Gary A. DeCrescenzo
  • Patent number: 5017587
    Abstract: The invention consists in healing of plantar warts with cycloheximide. Cycloheximide is used in various topical forms and methods of application to treat plantar warts. The concentrations employed ranges from 0.01% to 5.0% and the duration of treatment from 5 to 12 weeks.
    Type: Grant
    Filed: January 12, 1990
    Date of Patent: May 21, 1991
    Inventor: Leopoldo F. Montes
  • Patent number: 5001115
    Abstract: Prodrugs of bio-active hydroxyaromatic drugs having the structural formula:A pharmaceutically acceptable prodrug of a biologically active, therapeutically effective hydroxyaromatic drug, said prodrug being selected from the group consisting of, (A) compounds having the structural formula:DRUG--O--CR'R"--Z].sub.nwherein:DRUG --O-- is the hydroxyaromatic O-dehydro residue of said drug;R' and R' may be the same or different and may be H, alkyl, aryl or electron withdrawing groups;Z is a displaceable leaving group; andn is an integer in the range of from 1 to 3, and (B) pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: May 17, 1989
    Date of Patent: March 19, 1991
    Assignee: University of Florida
    Inventor: Kenneth B. Sloan
  • Patent number: 4975441
    Abstract: A composition suitable for topical application to mammalian skin or hair for inducing, maintaining or increasing hair growth comprises:(i) a chemical inhibitor of glycosidase activity chosen from lactams having the structure: ##STR1## where A.sup.1 and A.sup.6 are --H, --CH.sub.3, ##STR2## --CH.sub.2 OT or ##STR3## A.sup.1 and A.sup.6 being the same or different, and at least one of which being the group: ##STR4## in a lactam ring; and where Q is --OT', --NHT' or a lactam linkage to A.sup.1 or A.sup.6 ;the Q groups being the same or different, and at least one of which is involved in a lactam linkage;and where T is the same or different and is chosen from --H, --C.sub.p H.sub.2p+1 or a metal ion,T' is --H or --COC.sub.p H.sub.2p+1, andp is an integer of from 1 to 22;provided that:where any of the Q groups is --OT' or --NHT',then that group or groups can be of either stereochemical configuration with respect to the plane of the ring; and(ii) a cosmetically acceptable vehicle for the chemical inhibitor.
    Type: Grant
    Filed: March 22, 1989
    Date of Patent: December 4, 1990
    Assignee: Unilever Patent Holdings B.V.
    Inventor: Walter T. Gibson
  • Patent number: 4954510
    Abstract: A therapeutic and/or prophylactic agent for viral infection, particularly human immunodeficiency virus (HIV) infection, which comprises as an active ingredient a lactam compound represented by formula (I) ##STR1## wherein X represents --COOR, wherein R represents a hydrogen atom or a straight-chain or branched-chain alkyl group having from 1 to 8 carbon atoms, or ##STR2## wherein n represents an integer of 2 or 3 and A represents methine when n is 2 or a quarternary carbon atom when n is 3, or a pharmaceutically acceptable salt or ester derivative thereof.
    Type: Grant
    Filed: December 23, 1988
    Date of Patent: September 4, 1990
    Assignee: Meiji Seika Kaisha, Ltd.
    Inventors: Takashi Tsuroka, Satoru Nakabayashi, Yuji Matsuhashi, Haruo Yamamoto, Shigeharu Inouye, Shinichi Kondo
  • Patent number: 4952574
    Abstract: Certain 2,5-disubstituted N-(2-piperidylmethyl)benzamides, wherein one substituent is 2,2,2-trifluoroethyoxy, and pharmaceutically acceptable acid-addition salts thereof, are active as antiarrhythmic agents.
    Type: Grant
    Filed: September 26, 1988
    Date of Patent: August 28, 1990
    Assignee: Riker Laboratories, Inc.
    Inventor: Elden H. Banitt
  • 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: 4920101
    Abstract: This invention provides compositions comprising a physiologically-active agent and a compound represented by the general formula ##STR1## wherein X may represent sulfur, oxygen or 2 hydrogen radicals; Y may represent --CH.sub.2 --, --NH-- or oxygen; n and m are integers of from 1 to 3; p is an integer of from 3 to 17; q is 2, 4, 6 or 8; wherein p.gtoreq.9; and R' is selected from the group consisting of H, a lower alkyl group having from 1 to 4 carbon atoms, phenyl, lower alkyl or halogen substituted phenyl, acetamido, halogen, piperidinyl, lower alkyl or halogen substituted piperidinyl, carbalkoxy, carboxamide, and alkanoyl. These compositions are useful in topical or transdermal applications of the physiologically-active agent.
    Type: Grant
    Filed: September 30, 1987
    Date of Patent: April 24, 1990
    Assignee: Nelson Research & Development Co.
    Inventors: Gevork Minaskanian, James V. Peck
  • Patent number: 4918193
    Abstract: Disclosed is a process for synthesizing 3-[N-phenylacetylaminopiperidine]-2,6-dion, which process comprises the steps of providing a quantity of L-glutamine, providing a quantity of phenylacetyl halide, mixing together the L-glutamine and phenylacetyl halide in a weakly alkaline aqueous solution to provide an aqueous reaction mixture, adjusting the reaction mixture to a pH ranging from about 2 to about 3, and recovering from the reaction mixture the product 3-[N-phenylacetylamino-piperidine]-2,6-dion, and when desired preparing the pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: January 11, 1989
    Date of Patent: April 17, 1990
    Inventor: Stanislaw R. Burzynski
  • Patent number: 4886545
    Abstract: This invention provides compositions comprising a compound having the structural formula ##STR1## wherein each X, Y and Z may represent oxygen, sulfur or two hydrogen atoms, provided however that, when Z represents two hydrogen atoms, both X and Y represent oxygen or sulfur and when Z represents oxygen or sulfur at least one of X and Y must represent oxygen or sulfur; m is 2-6; R' is H or a lower alkyl group having 1-4 carbon atoms; n is 0-17 and R is --CH.sub.3, ##STR2## wherein R" is H or halogen. The invention also provides compositions comprising a physiologically-active agent and the hereinabove recited 1-substituted azacycloalkane compound in an amount effective to enhance the penetration of the physiologically-active agent through the skin or other membrane of the body of an animal.
    Type: Grant
    Filed: July 23, 1987
    Date of Patent: December 12, 1989
    Assignee: Nelson Research & Development Company
    Inventors: James V. Peck, Gevork Minaskanian
  • Patent number: 4886783
    Abstract: This invention relates to a method for administering systemically active agents including therapeutic agents through the skin or mucosal membranes of humans and animals in a transdermal device or formulation comprising topically administering with said systemic agent an effective amount of a membrane penetration enhancer having the structural formula ##STR1## wherein each X, Y and Z may represent oxygen, sulfur or two hydrogen atoms, provided however that, when Z represents two hydrogen atoms, both X and Y represent oxygen or sulfur and when Z represents oxygen or sulfur at least one of X and Y must represent oxygen or sulfur; m is 2-6; R' is H or a lower alkyl group having 1-4 carbon atoms; n is 0-16 and R is --CH.sub.3, ##STR2## wherein R" is H or halogen.
    Type: Grant
    Filed: August 17, 1988
    Date of Patent: December 12, 1989
    Assignee: Nelson Research & Development Co.
    Inventors: Gevork Minaskanian, James V. Peck
  • Patent number: 4879275
    Abstract: This invention relates to a method for administering systemically active agents including therapeutic agents through the skin or mucosal membranes of humans and animals in a transdermal device or formulation comnprising topically administering with said systemic agent an effective amount of a membrane penetration enhancer having the structural formula ##STR1## wherein X represents sulfur, oxygen or 2 hydrogen radicals; Y represents --CH.sub.2 --, --NH-- or oxygen; n and m are integers of from 1 to 3; p is an integer of from 3 to 17; wherein p.gtoreq.9; q is 2, 4, 6 or 8; and R' is selected from the group consisting of H, a lower alkyl group having from 1 to 4 carbon atoms, phenyl, lower alkyl or halogen substituted phenyl, acetamido, halogen, piperidinyl, lower alkyl or halogen substituted piperidinyl, carbalkoxy, carboxamide, and alkanoyl.
    Type: Grant
    Filed: May 27, 1988
    Date of Patent: November 7, 1989
    Assignee: Nelson Research & Development Co.
    Inventors: Gevork Minaskanian, James V. Peck
  • Patent number: 4877800
    Abstract: Phenyl-3-aminoalkyl-4-methyl-2,6-dioxopiperidines of the Formula I ##STR1## wherein: R.sub.1 represents hydrogen or C.sub.1 -C.sub.4 alkyl;n is 1 or 2;R.sub.2 represents hydrogen or methyl, provided that one R.sub.2 is hydrogen when n is 2;R.sub.3 represents hydrogen or C.sub.1 -C.sub.2 alkyl;R.sub.4 represents C.sub.1 -C.sub.2 alkyl;R.sub.5 and R.sub.6 independently represent hydrogen or methyl;m is 0 to 3; and each Y is in a meta or para position and independently represents hydroxy, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 hydroxyalkyl, halogen, or trifluoromethyl, provided that hydroxy and alkoxy are not in the para position, and pharmacologically acceptable salts thereof have antiposychotic activity without sedative side effects. They are particularly useful in the treatment of schizophrenia.The presently preferred compound is 3-(3'methoxyphenyl)-3-(3"-N,N-dimethylaminopropyl) -4,4-dimethyl-2,6-dioxopiperidine (AGN 2979).
    Type: Grant
    Filed: July 11, 1988
    Date of Patent: October 31, 1989
    Assignee: National Research Development Corporation
    Inventor: Brenda Costall
  • Patent number: 4871719
    Abstract: Novel 13-spiro-2'-[tetrahydrofuran]-milbemycins of the formula I ##STR1## in which X represents one of the groups --CH(OR.sub.1)--, --C(.dbd.O)-- or --C(.dbd.N--OH)--;R.sub.1 represents hydrogen or a OH-protecting group;R.sub.2 represents methyl, ethyl, isopropyl or sec.-butyl or the group --C(CH.sub.3).dbd.CH--A in which A represents methyl, ethyl or isopropyl; andR.sub.3 represents hydrogen; C.sub.1 -C.sub.10 -alkyl; C.sub.1 -C.sub.10 -alkyl substituted by at least one substituent selected from the group consisting of halogen, C.sub.1 -C.sub.6 -alkoxy, C.sub.2 -C.sub.6 -alkoxyalkoxy C.sub.3 -C.sub.9 -alkoxyalkoxyalkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.3 -C.sub.7 -cycloalkyl, C.sub.1 -C.sub.3 -alkyl-substituted C.sub.3 -C.sub.7 -cycloalkyl, hydroxy, benzyloxy, C.sub.1 -C.sub.6 -acyl and C.sub.1 -C.sub.6 -acyloxy, it being possible for each of the above-mentioned radicals representing or containing an alkoxy group to be terminally substituted at a terminal alkoxy group by hydroxy, halogen, C.sub.1 -C.sub.
    Type: Grant
    Filed: March 16, 1988
    Date of Patent: October 3, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Peter Maienfisch
  • Patent number: 4871750
    Abstract: Phenyl-3-aminoalkyl-4-methyl-2,6-dioxopiperidines of the Formula I ##STR1## wherein: R.sub.1 represents hydrogen or C.sub.1 -C.sub.4 alkyl;n is 1 or 2;R.sub.2 represents hydrogen or methyl, provided that one R.sub.2 is hydrogen when n is 2;R.sub.3 represents hydrogen or C.sub.1 -C.sub.2 alkyl;R.sub.4 representss C.sub.1 -C.sub.2 alkyl;R.sub.5 and R.sub.6 independently represent hydrogen or methyl;m is 0 to 3; andeach Y is in a meta or para position and independently represents hydroxy, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 hydroxyalkyl, halogen, or trifluoromethyl, provided that hydroxy and alkoxy are not in the para position.or pharmacologically acceptable acid addition salt thereof have analgesic activity. The compounds can be administered enterally, parenterally or topically. The topical compositions are novel.The presently preferred compound is 3-(3'methoxyphenyl)-3-(3"-N,N-dimethylaminopropyl)-4,4-dimethyl-2,6-dioxop iperidine (AGN 2979).
    Type: Grant
    Filed: June 14, 1988
    Date of Patent: October 3, 1989
    Assignee: National Research Development Corporation
    Inventor: Malcolm H. T. Roberts
  • 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: 4839370
    Abstract: Novel 3-aryl-3-cycloalkyl-piperidine-2,6-dione derivatives of the general formula I: ##STR1## in which A is a 4-aminophenyl radical or a pyridyl-(4)-radical and R.sub.1 is a saturated or unsaturated C.sub.3 -C.sub.10 -cycloalkyl radical or a C.sub.3 -C.sub.12 -alkenyl radical as well as physiologically acceptable salts thereof. The compounds are useful as inhibitors of estrogen biosynthesis. The compounds are made by a process which includes the step of heating a compound of the formula II ##STR2## wherein A and R.sub.1 have the meanings given above, and in addition A may also be a phenyl radical or a 4-nitrophenyl radical, X and Y are the same or different and repesent CN or COOC.sub.1 -C.sub.6 -alkyl and X or Y may also be COOH or a carboxylic acid ester group of the formula COOC.sub.1 -C.sub.6 -alkyl group, in a high boiling solvent at a temperature between 50.degree. and 200.degree. C. in particular between 80.degree. and 100.degree. C.
    Type: Grant
    Filed: July 31, 1987
    Date of Patent: June 13, 1989
    Assignee: Asta-Pharma AG
    Inventors: Rolf W. Hartmann, Christine Batzl
  • Patent number: 4837236
    Abstract: A heterocyclic compound of the formula: ##STR1## wherein A is an oxygen atom or a sulfur atom;B is either one of the groups: --CH.sub.2 --CHR.sup.1 -- or --CH.dbd.CR.sup.1 -- (in which R.sup.1 is a hydrogen atom or a methyl group);W is, the same or different, each a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group;X is either one of the following groups: ##STR2## (in which R.sup.2 is a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxy(lower)alkyl group, a hydroxyl group or a hydroxy(lower)alkyl group, R.sup.3 is a hydrogen atom or a lower alkyl group and n is an integer of 0 or 1);Z is, the same or different, each a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a halo(lower)alkyl group, a halo(lower)alkoxy group, a nitro group, a methylenedioxy group or a cyano group;p is an integer of 0 to 5; andq is an integer of 0 or 1, or its salt, which is useful as a fungicide.
    Type: Grant
    Filed: September 24, 1987
    Date of Patent: June 6, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Naoto Meki, Hirotaka Takano
  • Patent number: 4835151
    Abstract: Phenyl-3-aminoalkyl-4-methyl-2,6-dioxopiperidines of the Formula I ##STR1## wherein: R.sub.1 represents methoxy, ethoxy or hydroxy,R.sub.2 represents methoxy, ethoxy, hydroxy or hydrogen;each R.sub.3 independently represents methyl or ethyl;R.sub.4 represents hydrogen or methyl;R.sub.5 represents hydrogen or methyl; andn represents 2 or 3,and a pharmacologically acceptable acid addition salt thereof (a) have anxiolytic activity, (b) antagonize the anxiogenic activity of benzodiazepine inverse agonists, (c) reduce chronic abnormally high brain levels of serotonin or its metabolite 5-hydroxy-indoleacetic acid and (d) have antibacterial and antiviral activity. These activities are believed to be related to a reduction in serotonin turnover caused by blocking the depolarization activation of tryptophan hydroxylase. Novel compositions comprise the compounds with a benzodiazepine agonist or benzodiazepine inverse agonist.
    Type: Grant
    Filed: December 23, 1987
    Date of Patent: May 30, 1989
    Assignee: National Research Development Corporation
    Inventor: Maurice W. Gittos
  • Patent number: 4801603
    Abstract: A guanidinobenzoic ester derivative having the formula is novel and effective to inhibit enzymes such as trypsin, plasmin and thrombin, being useful for treatment of the pancreatitis and hemorrhagic disease and thrombosis. ##STR1## wherein X represents a group of the formula: ##STR2## in which Y is a group of the formula: --(CH.sub.2).sub.m --, m being an integer of 2 or 3, ##STR3## or a group of the formula:--ORin which R is a hydrogen atom or a lower alkyl group, and n represents an integer of 1 to 5.
    Type: Grant
    Filed: December 24, 1986
    Date of Patent: January 31, 1989
    Assignee: Eisai Co., Ltd.
    Inventors: Shigeru Souda, Naoyuki Shimomura, Norihiro Ueda, Shuhei Miyazawa, Takashi Yamanaka, Kaname Miyamoto, Ieharu Hishinuma, Junichi Nagakawa, Naoko Nagaoka, Hidetoshi Kawashima, Tsutomu Kawata, Junsaku Nagaoka, Tsuneo Wakabayashi
  • Patent number: 4738973
    Abstract: Phenyl-3-aminoalkyl-4-methyl-2,6-dioxopiperidines of the Formula I ##STR1## wherein: R.sub.1 represents methoxy, ethoxy or hydroxy,R.sub.2 represents methoxy, ethoxy, hydroxy or hydrogen;each R.sub.3 independently represents methyl or ethyl;R.sub.4 represents hydrogen or methyl;R.sub.5 represents hydrogen or methyl; andn represents 2 or 3,and a pharmacologically acceptable acid addition salt thereof (a) have anxiolytic activity, (b) antagonize the anxiogenic activity of benzodiazepine inverse agonists, (c) reduce chronic abnormally high brain levels of serotonin or its metabolite 5-hydroxy-indoleacetic acid and (d) have antibacterial and antiviral activity. These activities are believed to be related to a reduction in serotonin turnover caused by blocking the depolarization activation of tryptophan hydroxylase. Novel compositions comprise the compounds with a benzodiazepine agonist or benzodiazepine inverse agonist.
    Type: Grant
    Filed: September 10, 1986
    Date of Patent: April 19, 1988
    Assignee: National Research Development Corporation
    Inventor: Maurice W. Gittos
  • Patent number: 4731369
    Abstract: Amides and esters of 2-[N-(hydroxypiperidinoalkyl) and (hydroxypyrrolidinoalkyl) aminosulfonyl]-6-nitrobenzoic acids are disclosed to have activity in increasing the sensitivity of hypoxic tumor cells to therapeutic radiation. Also disclosed are methods of preparing such compounds, pharmaceutical compositions including such compounds and methods of treating patients in need of therapeutic radiation with effective amounts of such compounds.
    Type: Grant
    Filed: June 26, 1987
    Date of Patent: March 15, 1988
    Assignee: Merck & Co. Inc.
    Inventors: Edward L. Engelhardt, Walfred S. Saari
  • Patent number: 4705796
    Abstract: Composition of 3-N-phenylacetylamino-2,6-piperdinedione is disclosed as useful in the treatment of neuropsychiatric disorders involving monoamine oxidase regulation. 3-N-phenylacetylamino-2,6-piperidinedione has been shown to be an effective and selective MAO type B inhibitor.
    Type: Grant
    Filed: August 25, 1986
    Date of Patent: November 10, 1987
    Assignee: Stereochemical Genetics, Inc.
    Inventors: Lawrence B. Hendry, Ana H. Diamond, Bruce I. Diamond, Douglas E. Ewing
  • Patent number: 4663319
    Abstract: Novel thioketene derivatives of the formula: ##STR1## wherein R.sup.1 is hydrogen atom, an alkyl group, a lower alkenyl group, a phenyl group or a group of the formula: --B--Y;Y is a nitrogen-containing monocyclic heterocyclic group or a substituted or unsubstituted phenyl group;B is a straight or branched lower alkylene group;R.sup.2 and R.sup.3 are both a lower alkyl group or are combined together to form a group of the formula: --CH.sub.2 CH.sub.2 -- or --CH.dbd.CH--;R.sup.4 is hydrogen atom, a lower alkyl group or a (lower alkoxy)carbonyl group;A is a group of the formula: --(CH.sub.2).sub.n -- or --CH(COOR.sup.5)--;n is an integer of 0, 1 or 2 andR.sup.5 is a lower alkyl group,are disclosed. The compound (I) is useful as an agent for treating and protecting various liver diseases.
    Type: Grant
    Filed: January 7, 1985
    Date of Patent: May 5, 1987
    Assignee: Tanabe Seiysku Co., Ltd.
    Inventors: Ikuo Iijima, Koichi Homma, Yutaka Saiga, Yuzo Matsuoka, Mamoru Matsumoto
  • 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: 4593038
    Abstract: A cosmetic composition is provided which comprises 3-phenylacetylamino-2,6-piperidinedione dispersed in a cosmetically suitable vehicle. This cosmetic composition is useful in the topical cosmetic treatment of skin areas affected with wrinkles or hyperpigmentation.
    Type: Grant
    Filed: April 3, 1985
    Date of Patent: June 3, 1986
    Inventor: Stanislaw R. Burzynski
  • Patent number: 4558057
    Abstract: Highly purified fractions from human urine exhibiting antineoplastic activity and processes for their preparation are described. The fractions comprise biologically active, small sized, low molecular weight peptides which exert cytostatic and cytotoxic activity toward neoplastic cell cultures and human neoplastic diseases. The fractions have been termed antineoplaston fractions. An antineoplastic active peptide common to each of the various antineoplaston fractions has been isolated and identified as 3-[N-phenylacetylaminopiperidine]-2, 6-dion. A synthetic mechanism for the preparation of 3-[N-phenylacetylaminopiperdine]-2, 6-dion is also disclosed, involving a combination reaction between L-glutamine and phenylacetyl chloride. Also disclosed are the hydrolysis degradation products of 3-[N-phenylacetylaminopiperidine]-2, 6-dion which also exhibit antineoplastic activity when administered according to the general teachings presented in this disclosure.
    Type: Grant
    Filed: August 20, 1984
    Date of Patent: December 10, 1985
    Inventor: Stanislaw R. Burzynski
  • Patent number: 4533668
    Abstract: N-aralkylmoranoline and N-aralkenylmoranoline, and their pharmaceutical acceptable non-toxic acid addition salts thereof, pharmaceutical compositions containing the same and methods of inhibiting the increase in blood sugar level by administration of the same.
    Type: Grant
    Filed: April 27, 1979
    Date of Patent: August 6, 1985
    Assignee: Nippon Shinyaku Co. Ltd.
    Inventors: Shingo Matsumura, Hiroshi Enomoto, Yoshiaki Aoyagi, Yoshiaki Yoshikuni, Kohei Kura, Masahiro Yagi, Ichiro Shirahase
  • Patent number: 4528294
    Abstract: The present invention relates to new benzoyl-phenyl-piperidine derivatives selected from the group consisting of:(i) 2-piperidinobenzophenones of the general formula: ##STR1## in which: R.sub.1, R.sub.2 and R.sub.3, which are identical or different, each represent an atom of hydrogen, a hydroxy group, CF.sub.3, a halogen, a lower alkyl group or a lower alkoxy group;R.sub.4 represents an atom of hydrogen, a halogen, an NO.sub.2 group, an NR'R" group [where R' and R", which are identical or different, represent an atom of hydrogen, a lower alkyl group or a CO.sub.2 R group (where R represents a lower alkyl group or a benzyl group)];R.sub.5 and R.sub.6, which are identical or different, each represent an atom of hydrogen, a C.sub.1 -C.sub.4 -alkyl group, an OH group, a phenyl group or a benzyl group; and(ii) acid addition salts thereof.The invention also relates to the method for preparing these new derivatives and to their use in therapeutics, particularly as immunostimulant and immunoadjuvant agents.
    Type: Grant
    Filed: June 24, 1982
    Date of Patent: July 9, 1985
    Assignee: Societe de Recherches Industrielle S.O.R.I.
    Inventors: Bernard Majoie, Francois Bellamy, Pierre Dodey, Jacques Robin