Plural Chalcogens Bonded Directly To Ring Carbons Of The Piperidine Ring Patents (Class 514/328)
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Patent number: 5424319Abstract: Non-peptidyl compounds characterized generally as .alpha.-succinamidoacyl aminodiols having a piperidinyl-type group at the N-terminus are useful as renin inhibitors for the treatment of hypertension.Type: GrantFiled: December 16, 1993Date of Patent: June 13, 1995Assignee: G.D. Searle & Co.Inventors: Gunnar J. Hanson, John S. Baran
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Patent number: 5411970Abstract: 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: GrantFiled: December 21, 1993Date of Patent: May 2, 1995Assignee: G. D. Searle & Co.Inventors: Richard A. Partis, Francis J. Koszyk, Richard A. Mueller
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Patent number: 5378712Abstract: 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: GrantFiled: March 19, 1992Date of Patent: January 3, 1995Assignee: Hoffmann-La Roche IncInventors: Leo Alig, Paul Hadvary, Marianne Hurzeler, Marcel Muller, Beat Steiner, Thomas Weller
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Patent number: 5321031Abstract: 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: GrantFiled: September 23, 1992Date of Patent: June 14, 1994Assignee: Schering CorporationInventor: Sundeep Dugar
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Patent number: 5310745Abstract: 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: GrantFiled: August 13, 1992Date of Patent: May 10, 1994Assignee: G. D. Searle & Co.Inventors: Richard A. Partis, Francis J. Koszyk, Richard A. Mueller
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Patent number: 5300516Abstract: 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: GrantFiled: June 11, 1992Date of Patent: April 5, 1994Assignee: Pfizer Inc.Inventors: Alexander R. Mackenzie, Peter E. Cross
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Patent number: 5292750Abstract: 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: GrantFiled: September 8, 1992Date of Patent: March 8, 1994Assignee: Nippon Shinyaku Co. Ltd.Inventors: Yoshiaki Yoshikuni, Nobutoshi Ojima, Kazuya Mori
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Patent number: 5258518Abstract: 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: GrantFiled: April 1, 1992Date of Patent: November 2, 1993Assignee: G. D. Searle & Co.Inventors: Ish K. Khanna, Richard A. Mueller, Richard M. Weier
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Patent number: 5250545Abstract: 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: GrantFiled: December 3, 1990Date of Patent: October 5, 1993Assignee: Meiji Seika Kaisha, Ltd.Inventors: Tsutomu Tsuruoka, Satoru Nakabayashi, Harumi Fukuyasu, Yuuko Ishii, Takashi Tsuruoka, Haruo Yamamoto, Shigeharu Inouye, Shinichi Kondo
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Patent number: 5238947Abstract: 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: GrantFiled: May 21, 1991Date of Patent: August 24, 1993Assignees: University of Georgia Research Foundation, Inc., Stereochemical Genetics, Inc.Inventors: Lawrence B. Hendry, Chung K. Chu, Virendra B. Mahesh
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Patent number: 5206251Abstract: 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: GrantFiled: April 1, 1992Date of Patent: April 27, 1993Assignee: G. D. Searle & Co.Inventors: Ish K. Khanna, Richard A. Mueller, Richard M. Weier
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Patent number: 5198451Abstract: 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: GrantFiled: November 20, 1990Date of Patent: March 30, 1993Assignee: Novo Nordisk A/SInventors: Knud E. Andersen, Lars J. Stray Knudsen, Ursula Sonnewald, Per O. Sorensen
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Patent number: 5192772Abstract: 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: GrantFiled: August 12, 1991Date of Patent: March 9, 1993Assignee: Nippon Shinyaku Co. Ltd.Inventors: Yoshiaki Yoshikuni, Nobutoshi Ojima, Kazuya Mori
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Patent number: 5177086Abstract: 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: GrantFiled: July 12, 1991Date of Patent: January 5, 1993Assignee: National Research Development CorporationInventor: Brenda Costall
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Patent number: 5137886Abstract: 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: GrantFiled: December 6, 1990Date of Patent: August 11, 1992Assignee: Imperial Chemical Industries PLCInventors: Robin A. E. Carr, Donn W. Moseley, Nan C. Sillars
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Patent number: 5128347Abstract: 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: GrantFiled: October 18, 1990Date of Patent: July 7, 1992Assignee: Monsanto CompanyInventors: Daniel P. Getman, Gary A. DeCrescenzo
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Patent number: 5116622Abstract: 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: GrantFiled: September 12, 1990Date of Patent: May 26, 1992Inventor: Stanislaw R. Burzynski
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Patent number: 5093342Abstract: 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: GrantFiled: September 12, 1990Date of Patent: March 3, 1992Assignee: Aktiebolaget HassleInventors: Masaaki Tomoi, Yoshifumi Ikeda, Yoshiko Yokota
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Patent number: 5089508Abstract: 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: GrantFiled: September 4, 1990Date of Patent: February 18, 1992Inventor: Stanislaw R. Burzynski
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Patent number: 5051407Abstract: 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: GrantFiled: October 19, 1988Date of Patent: September 24, 1991Assignee: Bayer AktiengesellschaftInventors: Horst Boshagen, Bodo Junge, Gunther Kinast, Matthias Schuller, Jurgen Stoltefuss, Arnold Paessens
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Patent number: 5047425Abstract: 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: GrantFiled: November 30, 1988Date of Patent: September 10, 1991Assignee: Simes Societa Italiana Medicinali & Sintetici SpAInventors: Cesare Casagrande, Francesco Santangelo, Luisa Calabi
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Patent number: 5026713Abstract: 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: GrantFiled: August 29, 1989Date of Patent: June 25, 1991Assignee: Monsanto CompanyInventors: Daniel P. Getman, Gary A. DeCrescenzo
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Patent number: 5025021Abstract: 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: GrantFiled: July 27, 1989Date of Patent: June 18, 1991Assignee: Monsanto CompanyInventors: Daniel P. Getman, Gary A. DeCrescenzo
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Patent number: 5017587Abstract: 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: GrantFiled: January 12, 1990Date of Patent: May 21, 1991Inventor: Leopoldo F. Montes
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Patent number: 5001115Abstract: 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: GrantFiled: May 17, 1989Date of Patent: March 19, 1991Assignee: University of FloridaInventor: Kenneth B. Sloan
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Patent number: 4975441Abstract: 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: GrantFiled: March 22, 1989Date of Patent: December 4, 1990Assignee: Unilever Patent Holdings B.V.Inventor: Walter T. Gibson
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Patent number: 4954510Abstract: 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: GrantFiled: December 23, 1988Date of Patent: September 4, 1990Assignee: Meiji Seika Kaisha, Ltd.Inventors: Takashi Tsuroka, Satoru Nakabayashi, Yuji Matsuhashi, Haruo Yamamoto, Shigeharu Inouye, Shinichi Kondo
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Patent number: 4952574Abstract: 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: GrantFiled: September 26, 1988Date of Patent: August 28, 1990Assignee: Riker Laboratories, Inc.Inventor: Elden H. Banitt
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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: 4920101Abstract: 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: GrantFiled: September 30, 1987Date of Patent: April 24, 1990Assignee: Nelson Research & Development Co.Inventors: Gevork Minaskanian, James V. Peck
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Patent number: 4918193Abstract: 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: GrantFiled: January 11, 1989Date of Patent: April 17, 1990Inventor: Stanislaw R. Burzynski
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Patent number: 4886545Abstract: 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: GrantFiled: July 23, 1987Date of Patent: December 12, 1989Assignee: Nelson Research & Development CompanyInventors: James V. Peck, Gevork Minaskanian
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Patent number: 4886783Abstract: 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: GrantFiled: August 17, 1988Date of Patent: December 12, 1989Assignee: Nelson Research & Development Co.Inventors: Gevork Minaskanian, James V. Peck
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Patent number: 4879275Abstract: 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: GrantFiled: May 27, 1988Date of Patent: November 7, 1989Assignee: Nelson Research & Development Co.Inventors: Gevork Minaskanian, James V. Peck
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Patent number: 4877800Abstract: 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: GrantFiled: July 11, 1988Date of Patent: October 31, 1989Assignee: National Research Development CorporationInventor: Brenda Costall
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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: 4871719Abstract: 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: GrantFiled: March 16, 1988Date of Patent: October 3, 1989Assignee: Ciba-Geigy CorporationInventor: Peter Maienfisch
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Patent number: 4871750Abstract: 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: GrantFiled: June 14, 1988Date of Patent: October 3, 1989Assignee: National Research Development CorporationInventor: Malcolm H. T. Roberts
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Patent number: 4839370Abstract: 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: GrantFiled: July 31, 1987Date of Patent: June 13, 1989Assignee: Asta-Pharma AGInventors: Rolf W. Hartmann, Christine Batzl
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Patent number: 4837236Abstract: 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: GrantFiled: September 24, 1987Date of Patent: June 6, 1989Assignee: Sumitomo Chemical Company, LimitedInventors: Naoto Meki, Hirotaka Takano
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Patent number: 4835151Abstract: 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: GrantFiled: December 23, 1987Date of Patent: May 30, 1989Assignee: National Research Development CorporationInventor: Maurice W. Gittos
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Patent number: 4801603Abstract: 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: GrantFiled: December 24, 1986Date of Patent: January 31, 1989Assignee: 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
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Patent number: 4738973Abstract: 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: GrantFiled: September 10, 1986Date of Patent: April 19, 1988Assignee: National Research Development CorporationInventor: Maurice W. Gittos
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Patent number: 4731369Abstract: 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: GrantFiled: June 26, 1987Date of Patent: March 15, 1988Assignee: Merck & Co. Inc.Inventors: Edward L. Engelhardt, Walfred S. Saari
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Patent number: 4705796Abstract: 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: GrantFiled: August 25, 1986Date of Patent: November 10, 1987Assignee: Stereochemical Genetics, Inc.Inventors: Lawrence B. Hendry, Ana H. Diamond, Bruce I. Diamond, Douglas E. Ewing
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Patent number: 4663319Abstract: 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: GrantFiled: January 7, 1985Date of Patent: May 5, 1987Assignee: Tanabe Seiysku Co., Ltd.Inventors: Ikuo Iijima, Koichi Homma, Yutaka Saiga, Yuzo Matsuoka, Mamoru Matsumoto
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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: 4593038Abstract: 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: GrantFiled: April 3, 1985Date of Patent: June 3, 1986Inventor: Stanislaw R. Burzynski
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Patent number: 4558057Abstract: 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: GrantFiled: August 20, 1984Date of Patent: December 10, 1985Inventor: Stanislaw R. Burzynski
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Patent number: 4533668Abstract: 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: GrantFiled: April 27, 1979Date of Patent: August 6, 1985Assignee: Nippon Shinyaku Co. Ltd.Inventors: Shingo Matsumura, Hiroshi Enomoto, Yoshiaki Aoyagi, Yoshiaki Yoshikuni, Kohei Kura, Masahiro Yagi, Ichiro Shirahase