Plural Alicyclic Rings Patents (Class 562/498)
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Patent number: 5631291Abstract: The invention relates to cyclopentane- and -pentene-.beta.-amino acids, processes for their preparation and their use as medicaments.Type: GrantFiled: November 9, 1994Date of Patent: May 20, 1997Assignee: Bayer AktiengesellschaftInventors: Joachim Mittendorf, Franz Kunisch, Michael Matzke, Hans-Christian Militzer, Rainer Endermann, Karl G. Metzger, Klaus-Dieter Bremm, Manfred Plempel
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Patent number: 5576355Abstract: A method of inhibiting viruses in which a virus is contacted with diamondoid alcohol, ketone, ketone derivative, adamantyl amino acid, quaternary salt or combinations thereof which have antiviral properties. These diamondoid derivatives are shown to have antiviral activity against HIV.Type: GrantFiled: December 15, 1993Date of Patent: November 19, 1996Assignee: Mobil Oil Corp.Inventors: Catherine S. H. Chen, Dong-ming Shen
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Patent number: 5561124Abstract: The invention relates to substituted 17.alpha.-acyl steroidal 5.alpha.-reductase inhibiting compounds. The invention also relates to pharmaceutical compositions containing these compounds and their use for reducing prostate size and treating prostate adenocarcinoma. Further, the invention describes a process for making these compounds by heating the corresponding substituted 17.beta.-acyl steroid in a solvent, such as ethylene glycol or dimethyl sulfoxide (DMSO), in a base, such as sodium or potassium hydroxide.Type: GrantFiled: May 17, 1995Date of Patent: October 1, 1996Inventor: Robert L. Webb
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Patent number: 5449684Abstract: Compounds isolated from a marine sponge, and derivatives thereof, have the formulae: ##STR1## in which R.sup.1 is H or lower alkyl; R.sup.2 is OH or CH.sub.3 ; R.sup.3 is OH or CH.sup.3, and R.sup.4 H or MPTA. The compounds have antitumor and antiviral activity. The invention also provides pharmaceutical compositions containing the compounds and methods of treatment employing them.Type: GrantFiled: February 3, 1994Date of Patent: September 12, 1995Assignee: PharmaMar, S.A.Inventors: Jun-Ichi Tanaka, Tatsuo Higa, Khanit Suwanoborirux, C. W. Jefford, G. Bernardinelli, Dolores G. Gravalos
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Patent number: 5393924Abstract: Acylamides or amine acylate salts of arylalkanolamines are prepared by reacting an arylisonitrosoalkanone with hydrogen and a carboxylic acid, carboxylic acid anhydride or carboxylic acid ester or mixture thereof in the presence of a transition metal catalyst; optionally the product is converted to the corresponding arylalkanolamine hydrochloride salt by reaction of the acylamide or amine acylate salt of the arylalkanolamine with hydrogen chloride in a C.sub.1 -C.sub.3 alkyl alcohol.Type: GrantFiled: April 29, 1994Date of Patent: February 28, 1995Assignee: Hoechst Celanese CorporationInventors: Ahmed M. Tafesh, Olan S. Fruchey, Charles B. Hilton
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Patent number: 5374654Abstract: The invention relates to carbacyclin derivatives of Formula I ##STR1## wherein the various substituents are defined herein, including, inter alia,if R.sub.2 is a hydrogen atom, their salts with physiologically compatible bases, their cyclodextrin clathrates, and their use as medicinal agents.Type: GrantFiled: April 21, 1993Date of Patent: December 20, 1994Assignee: Schering AktiengesellschaftInventors: Helmut Vorbruggen, Ulrich Klar, Bob Nieuweboer, Claus-Steffen Sturzebecher
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Patent number: 5264586Abstract: Chimeric analogs of calicheamicin that include an analog of calicheamicinone linked to an ester or glycoside, (-)-calicheamicinone and its analogs are disclosed.Type: GrantFiled: July 16, 1992Date of Patent: November 23, 1993Assignee: The Scripps Research InstituteInventors: Kyriacos C. Nicolaou, Adrian L. Smith, Chan-Kou Hwang, Emmanuel Pitsinos
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Patent number: 5248807Abstract: The present invention provides triterpene derivatives of the following formula: ##STR1## wherein, R.sup.1 is hydrogen or metabolic ester-residue; R.sup.3 is optionally substituted aryl or optionally substituted aromatic heterocycle; X is hydrogen and Y is hydroxy or X and Y may form together oxo; Z is an oxygen or two hydrogen atoms, or the salts thereof, which have anti-endothelin activities and are useful for preventing or treating cardiovascular failure, and pharmaceutical compositions thereof.Type: GrantFiled: July 8, 1992Date of Patent: September 28, 1993Assignee: Shionogi & Co., Ltd.Inventors: Masafumi Fujimoto, Kensuke Sakurai, Shinichi Mihara, Miharu Nakamura, Toshiro Konoike
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Patent number: 5235119Abstract: An efficient direct functionalization of nitrocubanes has been achieved by irradiation of a solution in an oxalyl halide to yield halogenated and halocarbonylated derivatives of nitrocubanes.Type: GrantFiled: October 1, 1992Date of Patent: August 10, 1993Assignee: The United States of America as represented by the Secretary of the ArmyInventor: Abdollah Bashir-Hashemi
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Patent number: 5232836Abstract: Vitamin D derivatives corresponding to the following formula I ##STR1## in which R.sub.1 denotes a substituted alkyl group having 1 to 15 carbon atoms, in particular the side chains of vitamin D.sub.2 (C.sup.20 to C.sup.28) or D.sub.3 (C.sup.20 to C.sup.Type: GrantFiled: February 18, 1992Date of Patent: August 3, 1993Assignee: Ire-Medgenix S.A.Inventors: Roger Bouillon, Pierre J. De Clerco, Pierre Eliard, Maurits Vanderwalle
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Patent number: 5214221Abstract: An efficient direct functionalization of nitrocubanes has been achieved by rradiation of a solution in an oxalyl halide to yield halogenated and halocarbonylated derivatives of nitrocubanes.Type: GrantFiled: October 1, 1992Date of Patent: May 25, 1993Assignee: The United States of America as represented by the Secretary of the ArmyInventor: Abdollah Bashir-Hashemi
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Patent number: 5206416Abstract: An isocarbacyclin derivative represented by the following formula: ##STR1## wherein R.sup.1 represents H or a linear or branched C.sub.1 -C.sub.10 alkyl group, R.sup.2 represents H, a methyl group or a vinyl group, and R.sup.3 represents an unsubstituted linear or branched C.sub.3 -C.sub.8 alkyl group or a C.sub.5 -C.sub.6 cycloalkyl group. and a pharmaceutaically acceptable salt thereof.Type: GrantFiled: September 24, 1991Date of Patent: April 27, 1993Assignee: Teijin LimitedInventor: Seizi Kurozumi
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Patent number: 5192798Abstract: This invention relates to novel lipophilic polyamines of formula I, the method of using these compounds to treat hypercholesterolemia, and intermediates thereto.Z.sub.1 --(CH.sub.2).sub.n --Y.sub.1 --X.sub.1 --R.sub.Type: GrantFiled: August 16, 1990Date of Patent: March 9, 1993Assignee: The Upjohn CompanyInventors: James W. Aiken, Charles H. Spilman, Edward W. Thomas
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Patent number: 5190964Abstract: 5-fluorocarbacyclin derivatives of the Formula I ##STR1## wherein R.sub.1 is CH.sub.2 OH orA is --CH.sub.2 --CH.sub.2 --, trans --CH.dbd.CH-- or --C.tbd.C--,W is a free or functionally modified hydroxymethylene group or free or functionally modified ##STR2## in which the OH group can be in the .alpha.-- or .beta.-position, D is ##STR3## a C.sub.1-10 -aliphatic group (e.g., alkyl or alkenyl) which optionally can be substituted by fluorine atoms,n is 1, 2 or 3,E is a direct bond, --C.tbd.C-- or --CR.sub.6 .tbd.CR.sub.7 -- in which R.sub.6 represents a hydrogen atom or an alkyl group with 1-5 atoms and R.sub.7 represents a hydrogen atom, a halogen atom or an alkyl group with 1-5 C atoms,R.sub.4 is alkyl, cycloalkyl or optionally substituted aryl or a heterocyclic group,R.sub.5 is a free or functionally modified hydroxy groupand, when R.sub.2 is a hydrogen atom, its salts with physiologically compatible bases,have valuable pharmacological properties.Type: GrantFiled: February 15, 1990Date of Patent: March 2, 1993Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Martin Haberey, Claus-Steffen Sturzebecher, Michael-Harold Town
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Patent number: 5162353Abstract: The invention relates to carbacyclin derivatives with general formula I: ##STR1## in which Y.sub.1 stands for the radical --CH.sub.2 --X--(CH.sub.2).sub.n --R.sub.1 or the radical ##STR2## n, 1 or 3, R.sub.1, the radical ##STR3## the radical ##STR4## R.sub.9 stands for the radical --(CH.sub.2).sub.m --R.sub.6 or the radical --(CH.sub.2).sub.m-o --[Z.sub.1 --(CH.sub.2).sub.m-p ].sub.x --[Z.sub.2 --(CH.sub.2).sub.m-q ].sub.y --R.sub.6,m=2-20,o, p, and q are less than or equal to 19,x, y=0, 1 or 2,Z.sub.1 stands for a cis--CH.dbd.CH group, a trans--CH.dbd.CH group of a --C.dbd.C group, and each of these groups must be separated at least by a methylene group from the C-9 carbon atom of the carbacyclin bicyclic compound,Z.sub.2 stands for oxygen, sulfur, an NH or an N methyl group,R.sub.6 stands for amino, methylamino, hydroxy, carboxy or mercapto,X an oxygen atom or a methylene group,Y.sub.2 hydrogen or fluorine,A a --CH.sub.2 --CH.sub.2, trans--CH.dbd.CH or --C.dbd.Type: GrantFiled: August 21, 1990Date of Patent: November 10, 1992Assignee: Schering AktiengesellschaftInventors: Helmut Vorbrueggen, Bob Nieuweboer, Claus-Steffen Stuerzebecher
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Patent number: 5159102Abstract: 7-thiaprostaglandins E.sub.1 which are compounds represented by the following formula [I] or their enantiomers or mixtures thereof in any ratio: ##STR1## where R.sup.1 represents a hydrogen atom, a C.sub.1 -C.sub.10 alkyl group, a C.sub.2 -C.sub.20 alkenyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted C.sub.3 -C.sub.10 cycloalkyl group, a substituted or unsubstituted phenyl (C.sub.1 -C.sub.2) alkyl group, or one equivalent cation; R.sup.2 and R.sup.3, which may be the same or different, represent a hydrogen atom, a tri (C.sub.1 -C.sub.7) hydrocarbon silyl group, or a group forming an acetal linkage together with an oxygen atom of a hydroxyl group; R.sup.4 represents a hydrogen atom, a methyl group or a vinyl group; R.sup.5 represents a linear or branched C.sub.3 -C.sub.8 alkyl group, a linear or branched C.sub.3 -C.sub.8 alkenyl group, a linear or branched C.sub.2 -C.sub.Type: GrantFiled: May 22, 1990Date of Patent: October 27, 1992Assignee: Teijin LimitedInventors: Toshio Tanaka, Kiyoshi Bannai, Atsuo Hazato, Seizi Kurozumi
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Patent number: 5124343Abstract: The invention relates to carbacyclins of general Formula I ##STR1## wherein R.sub.1 is the residue CH.sub.2 OH or ##STR2## with R.sub.2 meaning a hydrogen atom, an alkyl, cycloalkyl, aryl residue, a ##STR3## or heterocyclic residue, or R.sub.1 is the residue ##STR4## with R.sub.3 meaning an alkanoyl or alkanesulfonyl residue of respectively 1-10 carbon atoms or the residue R.sub.2, orR.sub.1 is the residue ##STR5## wherein m is the number 1 or 2, X is an oxygen atom or a CH.sub.2 -group,A is a trans--CH.dbd.CH- or --.tbd.C--group,W is a free or functionally modified hydroxymethylene group wherein the OH-group can be in the .alpha.- or .beta.- position,n is the number 1, 2, or 3,D is a straight-chain alkylene group of 1-5 carbon atoms,E is a --C.tbd.C---bond or a --CR.sub.6 =CR.sub.7 --group wherein R.sub.6 and R.sub.7 are different from each other and mean a hydrogen atom or an alkyl group of 1-5 carbon atoms or a hydrogen atom or a halogen atom, preferably chlorine,R.sub.Type: GrantFiled: January 6, 1988Date of Patent: June 23, 1992Assignee: Schering AktiengesellschaftInventors: Helmut Vorbrueggen, Hernd Raduechel, Werner Skuballa, Norbert Schwarz, Jorge Casals-Stenzel, Gerda Mannesmann, Michael H. Town
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Patent number: 5109021Abstract: The present invention relates to novel isomers of PGAs, PGDs, PGEs, PGFs, 6-keto-PGE.sub.1 s, 6-keto-PGF.sub.1 s, PGI.sub.2 s, 6,9.alpha.-nitrilo-PGI.sub.1 s and 6,9.alpha.-methano-PGI.sub.2 s, having a specific steric configuration, which are replaced by an alkyl (C.sub.1 to C.sub.8)-substituted cycloalkyl (C.sub.4 to C.sub.7) group in (1S,S) form, in (1S,R) form or in cis form at the 15-, 16- or 17-position of the PG skeleton, and, alkyl esters thereof, non-toxic salts thereof, non-toxic acid addition salts thereof and cyclodextrin clathrates thereof, possessing more potent PG-like pharmacological activity than other isomers.Type: GrantFiled: May 25, 1990Date of Patent: April 28, 1992Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Katsuhiro Imaki, Hajimu Miyake, Tadao Okegawa
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Patent number: 5100917Abstract: The present invention relates to novel A-nor-steroid-3-carboxylic acid derivatives and to their use as inhibitors of mammalian 5.alpha.-reductase.Type: GrantFiled: September 11, 1990Date of Patent: March 31, 1992Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Gary A. Flynn, Philippe Bey, Thomas R. Blohm
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Patent number: 5093519Abstract: Vitamin D derivatives corresponding to the following formula I ##STR1## in which R.sub.1 denotes a substituted alkyl group having 1 to 15 carbon atoms, in particular the side chains of vitamin D.sub.2 (C.sup.20 to C.sup.28) or D.sub.3 (C.sup.20 to C.sup.Type: GrantFiled: May 1, 1989Date of Patent: March 3, 1992Assignee: Ire-Medgenix S.A.Inventors: Roger Bouillon, Pierre J. De Clercq, Pierre Eliard, Maurits Vandewalle
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Patent number: 5084592Abstract: Azulenesquaric acid dyes of the formula ##STR1## where R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 each have specified meanings are prepared from azulene derivatives of the formula ##STR2## where R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 each have specified meanings as intermediates, and used in an optical recording medium.Type: GrantFiled: September 30, 1988Date of Patent: January 28, 1992Assignee: BASF AktiengesellschaftInventors: Wolfgang Schrott, Peter Neumann, Sibylle Brosius, Helmut Barzynski, Klaus D. Schomann, Harald Kuppelmaier
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Patent number: 5036104Abstract: 2-Acylaminoalkyl-3-[1-(carboxycycloalkylcarbamoyl)cycloalkyl]propanoic acid derivatives (which may also be viewed as glutaramide derivatives) are useful in the treatment of hypertension, heart failure and renal insufficiency, based upon their inhibition of zinc-dependent, neutral endopiptidase.Type: GrantFiled: June 14, 1990Date of Patent: July 30, 1991Assignee: Pfizer Inc.Inventors: John C. Danilewicz, Keith James
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Patent number: 4983627Abstract: Compounds useful in treating or preventing gastrointestinal ulcers and in treating cardiovascular disorders such as thrombosis, hypertension and atherosclerosis are depicted in formulas (1), (2) and (3): ##STR1## wherein: A is --C.tbd.C--, trans --HC.dbd.CH--, trans --CH.dbd.CHCH.sub.2 -- or --CH.sub.2 CH.sub.2 --;X is lower alkyl of 1-6 carbon atoms;Y is hydrogen, exo-(lower alkyl) or endo-(lower alkyl);n is an integer from 2-4;R.sub.1 is --CH.sub.2 OH, --CHO, --CO.sub.2 R or --CO.sub.2 H, and the olefin formed by the R.sub.1 (CH.sub.2).sub.n CH.dbd. moiety is either (E) or (Z);R.sub.2 is hydrogen or methyl, or optionally --CH.dbd.CH.sub.2 when A is trans --CH.dbd.CHCH.sub.2 --; andR.sub.3 is linear or branched alkyl, alkenyl or alkynyl having 5-10 carbon atoms, ##STR2## --(CH.sub.2).sub.m -phenyl or CH.sub.2 O-phenyl; in which each phenyl may be optionally substituted with lower alkyl, lower alkoxy, trifluoromethyl, or halogen.Type: GrantFiled: November 10, 1988Date of Patent: January 8, 1991Assignee: Syntex (U.S.A.) Inc.Inventors: Counde O'Yang, Walter Kurz, Keith A. M. Walker, Helen Y. Wu
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Patent number: 4971987Abstract: The invention also relates to carbacyclin derivatives of general formula I' ##STR1## wherein R.sub.9 is an alkyl group of 1-10 carbon atoms or the group --C.dbd.C--(CH.sub.2).sub.m --R.sub.6 whereinm is 1 to 16 andR.sub.6 is hydroxy on amino.Type: GrantFiled: March 7, 1988Date of Patent: November 20, 1990Assignee: Schering AktiengesellschaftInventors: Helmut Vorbrueggen, Bob Nieuweboer, Claus-Steffen Stuerzebecher, Ulrich Klar
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Patent number: 4963585Abstract: The invention relates to a compound of antimicrobial activity of the formula ##STR1## wherein R.sup.1 is hydrogen or lower alkanoyl,R.sup.2 is hydrogen or ##STR2## in which R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are hydrogen or lower alkanoyl,R.sup.3 is carboxy or a protected carboxy, and pharmaceutically acceptable salt thereof.Type: GrantFiled: February 14, 1989Date of Patent: October 16, 1990Assignee: Fujisawa Pharmaceutical Company, Ltd.Inventors: Masanori Okamoto, Eisaku Tsujii, Tsutomu Kaizu, Hiroshi Hatanaka, Masakuni Okuhara, Kozo Sawada, Hirokazu Tanaka
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Patent number: 4954524Abstract: Carbacyclin derivatives of Formula I ##STR1## wherein R.sub.1 is hydrogen or OR.sub.2, wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, ##STR2## or a heterocyclic residue; or R.sub.1 is NHR.sub.3 wherein R.sub.3 is an acid residue (acyl) or R.sub.2,n is 2, 3, 4, or 5,X is hydrogen or fluorine,A is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH--, or --C.tbd.C--,W is a free or functionally modified hydroxymethylene group or a free or functionally modified ##STR3## wherein the OH-group can be in the .alpha.- or .beta.-position, D is ##STR4## a straight-chain, saturated aliphatic group of 1-10 carbon atoms, a branched, saturated or a straight-chain or branched, unsaturated aliphatic group of 2-10 carbon atoms, all of which can optionally be substituted by fluorine atoms,m is 1, 2, or 3,E is a direct bond, --C.tbd.C--, or --CR.sub.6 .dbd.CR.sub.7 -- wherein R.sub.6 and R.sub.7 are different from each other and are hydrogen or alkyl or 1-5 carbon atoms, or are hydrogen or halogen,R.sub.Type: GrantFiled: April 6, 1989Date of Patent: September 4, 1990Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Jorge Casals-Stenzel, Gerda Mannesmann, Ekkehard Schillinger, Michael H. Town
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Patent number: 4894181Abstract: Carbocyclic compounds of the formula I ##STR1## wherein Q is a benzene or cyclohexane ring or a naphthalene system, X is in each case --CH.sub.2 --(CH.sub.2).sub.p -- where it is also possible for one or two non-adjacent CH.sub.2 groups to be replaced by --O--, --S--, --CO--, --O--CO--, --CO--O-- or --CH.dbd.CH--,p is 0, 1 or 2,A.sup.1 and A.sup.2 independently of one another are each a 1,4-phenylene group which is unsubstituted or monosubstituted or polysubstituted by halogen atoms and/or CH.sub.3 groups and/or CN groups and in which it would also be possible for one or more CH groups to be replaced by N atoms, a 1,4-cyclohexylene group wherein it would also be possible for one or two non-adjacent CH.sub.2 groups to be replaced by --O-- and/or --S--, a piperidine-1,4-diyl group or a 1,4-bicyclo[2.2.2]octylene group,Z is --CO--O--, --O--CO--, --O--, --CH.sub.2 --, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CHCN--CH.sub.2 --, --CH.sub.2 --CHCN--, --CH.dbd.CH--, --CH.dbd.N--, --N.dbd.CH--, --NO.Type: GrantFiled: May 16, 1988Date of Patent: January 16, 1990Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Klaus Praefcke, Bernd Kohne, Eike Poetsch
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Patent number: 4833271Abstract: Structurally-defined, low molecular weight oligomers and preparation thereof which are active in the protection of oxidative physphorylation of mitochondria and exhibit ionophoretic activity. Said structurally defined low molecular weight oligomers are synthesized using a modified 15-dehydro PGB.sub.1 such as 16,16-dimethyl-15-dehydro prostaglandin B.sub.1 as a precursor to obtain oligomeric mixtures which are structurally defined and active in the protection of oxidative phosphorylation and exhibit ionophoretic activity. Synthesis of modified 15-dehydro-PGB.sub.1 ; 16,16-dimethyl-15-dehydro-prostagalandin B.sub.1 ; is also described.Type: GrantFiled: August 23, 1985Date of Patent: May 23, 1989Inventor: George L. Nelson
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Patent number: 4824999Abstract: The compound which is 2,3,3a,3b,4,5,6,6a,7,7a-decahydro-4,6,7-metheno-1H-cyclopenta[a]pentalene- 1,3-dicarboxylic acid is useful as an intermediate for production of the corresponding anhydride from which several of the disclosed antipsychotic/anxiolytic agents are prepared.Type: GrantFiled: September 23, 1988Date of Patent: April 25, 1989Assignee: American Home Products CorporationInventor: Gary P. Stack
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Patent number: 4797488Abstract: Substituted imides of the following formula are antipsychotic, anxiolytic agents with very little extrapyramidal side effects: ##STR1## in which X is --O--, --S--, --SO--, --SO.sub.2 --, --CR.sub.3 R.sub.4 -- where R.sub.3 and R.sub.4, independently, are hydrogen, alkyl of 1 to 4 carbon atoms or, taken together with the carbon atom to which they are attached, R.sub.3 and R.sub.4 form a cycloalkyl group of of 3 to 5 carbon atoms; n is one of the integers 2, 3, 4 or 5; R is phenyl, halophenyl, trifluoromethylphenyl, alkoxyphenyl in which the alkoxy substituent contains 1 to 3 carbon atoms, 2-pyrimidinyl, halopyrimidin-2-yl, 2-pyrazinyl, halopyrazin-2-yl, 2-pyridinyl, cyanopyridin-2-yl, halopyridin-2-yl, quinolyl, or haloquinolyl; R.sub.1 and R.sub.2, taken together, are alkylene of 3 to 5 carbon atoms or alkenylene of 3 to 5 carbon atoms, or taken with the carbon atoms to which they are attached, R.sub.1 and R.sub.2 complete a benzene ring, or a group of the formula: ##STR2## where Y is --CH.sub.2 --, --CH.sub.Type: GrantFiled: April 3, 1987Date of Patent: January 10, 1989Assignee: American Home Products CorporationInventors: Gary P. Stack, Thomas D. Golobish, Magid A. Abou-Gharbia
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Patent number: 4792550Abstract: A novel 13-aza-14-oxo-TXA.sub.2 analogue of general formula: ##STR1## wherein symbol A represents --CH.sub.2 CH.sub.2 --(CH.sub.2).sub.m --, cis--CH.dbd.CH--(CH.sub.2).sub.m --, --CH.sub.2 O--(CH.sub.2).sub.m --, --S--(CH.sub.2).sub.m -- ##STR2## R.sup.2 represents a bond or a straight or branched alkylene or alkenylene group of from 1 to 10 carbon atom(s) unsubstituted or substituted;R.sup.3 represents(i) a phenyl, phenoxy or phenylthio group unsubstituted or substituted,(ii) a straight or branched alkyl, alkenyl or alkynyl group of from 1 to 6 carbon atom(s) unsubstituted or substituted,(iii) a cycloalkyl, cycloalkyloxy or cycloalkylthio group of from 4 to 7 carbon atoms unsubstituted or substituted,(iv) a naphthyl, indolyl or indanyl group, or(v) an amino group unsubstituted or substitutedR.sup.4 represents a hydrogen atom or a methyl group.Type: GrantFiled: June 11, 1985Date of Patent: December 20, 1988Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Hajimu Miyake, Tadao Okegawa, Akiyoshi Kawasaki
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Patent number: 4788332Abstract: Sweeteners of the formula: ##STR1## and food-acceptable salts thereof, where the substituents are disclosed herein.Type: GrantFiled: January 19, 1988Date of Patent: November 29, 1988Assignee: General Foods CorporationInventors: Paul R. Zanno, Ronald E. Barnett, Glenn M. Roy
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Patent number: 4764528Abstract: Novel 2,4-pentadienoic acid derivatives are disclosed. As the examples are mentioned 3-(4-carboxy-trans, trans-1,3-butadienyl)-6-exo-(3.alpha.-hydroxy-trans-1-octenyl)-7-endo-hydr oxybicyclo[3.3.0]oct-2-ene, 3-(5-carboxy-trans, trans-2,4-pentadienyl)-6-exo-(3.alpha.-hydroxy-trans-1-octenyl)-7-endo-hyd roxybicyclo[3.3.0]oct-2-ene and the like. These compounds are useful as a platelet aggregation inhibitor, especially as a thrombosis-prophylactic agent.Type: GrantFiled: March 10, 1987Date of Patent: August 16, 1988Assignee: Teruo Kabushiki KaishaInventors: Keiko Chiba, Makoto Takai, Toshio Wakabayashi
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Patent number: 4735966Abstract: Compounds useful in treating cardiovascular disorders such as thrombosis, hypertension and atherosclerosis are depicted in formulas (1), (2) and (3): ##STR1## wherein: A is --C.tbd.C--, trans --HC.dbd.CH--, --CH.sub.2 CH.sub.2 -- or --CH.dbd.CHCH.sub.2 --;X is lower alkoxy, hydroxy, or (2,2,2)-trifluoroethoxy;Y is hydrogen, exo-(lower alkyl) or endo-(lower alkyl);is an integer of 2-4;R.sub.1 is --CH.sub.2 OH, --CHO, --CO.sub.2 R or --CO.sub.2 H, and the olefin formed by the R.sub.1 (CH.sub.2).sub.n CH.dbd. moiety is either (E) or (Z);R.sub.2 is hydrogen or methyl, or optionally --CH.dbd.CH.sub.2 when A is --CH.dbd.CHCH.sub.2 --; andR.sub.3 is linear or branched alkyl, alkenyl or alkynyl having 5-10 carbon atoms, ##STR2## --(CH.sub.2).sub.m -phenyl or CH.sub.Type: GrantFiled: August 25, 1986Date of Patent: April 5, 1988Assignee: Syntex (U.S.A.) Inc.Inventors: Helen Y. Wu, Walter Kurz
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Patent number: 4708963Abstract: Carbacyclin derivatives of Formula I ##STR1## wherein R.sub.1 is OR.sub.2, wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, a heterocyclic residue, or NHR.sub.3, wherein R.sub.3 is an acid residue or hydrogen;X is oxygen;A is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH--, or --C.tbd.C--;W is free or functionally modified hydroxymethylene or free or functionally modified ##STR2## wherein the OH-group can be in the .alpha.- or .beta.-position; D is a straight-chain or branched, saturated or unsaturated aliphatic group of 1-10 carbon atoms, which can optionally be substituted by fluorine atoms, 1,2-methylene, 1,1-trimethylene;E is --C.tbd.C-- or --CR.sub.6 .dbd.CH.sub.7 -- wherein R.sub.6 and R.sub.7 are hydrogen or alkyl of 1-5 carbon atoms;R.sub.4 is an aliphatic group, cycloalkyl, optionally substituted aryl, or a heterocyclic group;R.sub.5 is free or functionally modified hydroxy and,when R.sub.Type: GrantFiled: May 28, 1985Date of Patent: November 24, 1987Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduchel, Norbert Schwarz, Helmut Vorbruggen, Jorge Casals-Stenzel, Ekkehard Schillinger, Michael H. Town
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Patent number: 4701552Abstract: This invention relates to novel sweeteners of the formula: ##STR1## wherein A is hydrogen, alkyl containing 1-3 carbon atoms, hydroxyalkyl containing 1-3 carbon atoms, alkoxymethyl wherein the alkoxy contains 1-3 carbon atoms or --CO.sub.2 R in which R is alkyl containing 1-3 carbon atoms;A' is hydrogen or alkyl containing 1-3 carbon atoms;A and A' taken together with the carbon atom to which they are attached form cycloalkyl containing 3-4 carbon atoms;Y is --(CHR.sub.2).sub.n -R.sub.1 or --CHR.sub.3 R.sub.4 ;R.sub.1 is alkyl-substituted cycloalkyl, cycloalkenyl, bicycloalkyl or bicycloalkenyl containing at least one alkyl in the .beta.-position of the ring, up to 7 ring carbon atoms and up to a total of 12 carbon atoms;R.sub.2 is H or alkyl containing 1-4 carbon atoms;R.sub.3 and R.sub.4 are each cycloalkyl containing 3-4 ring carbon atoms;n=0 or 1; andm=0 or 1;and food-acceptable salts thereof.Type: GrantFiled: March 21, 1986Date of Patent: October 20, 1987Assignee: General Foods CorporationInventors: Paul R. Zanno, Ronald E. Barnett, Glenn M. Roy
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Patent number: 4698363Abstract: Prostaglandin analogues of the formula: ##STR1## (wherein R.sup.1 represents a hydrogen atom or an aliphatic or alicyclic hydrocarbon radical, Y.sup.1 represents a carbonyl or hydroxymethylene group, A.sup.1 represents an alkylene linkage containing 1, 2 or 3 carbon atoms and optionally bearing a methyl or ethyl substituent, R.sup.2 represents a hydrogen atom or a methyl or ethyl group and R.sup.3 represents a hydrogen atom or R.sup.2 and R.sup.3 form an alkylene linkage containing 2 or 3 carbon atoms, optionally bearing a methyl or ethyl substituent, such that the symbols A.sup.1, R.sup.2 and R.sup.3, together with the carbon atoms through which they are connected, may form a cycloalkyl ring of 5, 6, 7 or 8 carbon atoms, optionally bearing one or two methyl or ethyl substituents, or A.sup.1 and R.sup.Type: GrantFiled: November 20, 1985Date of Patent: October 6, 1987Assignee: May & Baker LimitedInventor: Terance W. Hart
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Patent number: 4692464Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is (a) hydrogen, (b) C.sub.1-10 alkyl, (c) C.sub.1-10 alkyl substituted by halogen; C.sub.1-4 alkoxy; C.sub.6-10 aryl; C.sub.6-10 aryl substituted by 1-3 halogen atoms, a phenyl group, 1-3 C.sub.1-4 alkyl groups or a chloromethyl, fluoromethyl, trifluoromethyl, carboxy, hydroxy or C.sub.1-4 alkoxy group; di-C.sub.1-4 -alkylamino; or tri-C.sub.1-4 -alkylammonium, (d) C.sub.4-10 cycloalkyl, (e) C.sub.4-10 cycloalkyl substituted by C.sub.1-4 alkyl, (f) C.sub.6-10 aryl, (g) C.sub.6-10 aryl substituted by 1-3 halogen atoms, a phenyl group 1-3 C.sub.1-4 alkyl groups or a chloromethyl, fluoromethyl, trifluoromethyl, carboxy, hydroxy or C.sub.1-4 alkoxy group, or (h) an aromatic heterocycle of 5 or 6 ring atoms one of which is O, N or S;A is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH-- or --C.tbd.C--;W is hydroxymethylene, RO-methylene, CH.sub.3 or CH.sub.3, ##STR2## wherein OH or OR is in the .alpha.- or .beta.Type: GrantFiled: February 26, 1982Date of Patent: September 8, 1987Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Gerda Mannesmann, Wolfgang Losert, Jorge Casals
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Patent number: 4689344Abstract: A novel class of compounds has been found to be effective in blocking cholesterol and neutral lipid synthesis in-vivo without adversely affecting energy metabolism, useful for the treatment of obesity, hyperlipidemia and maturity-onset diabetes. The active compounds have the general formula ##STR1## or in-vivo hydrolyzable functional derivatives of the carboxylic groups thereof,whereinR.sub.1 and R.sub.2 each independently represents an unsubstituted or substituted hydrocarbyl or hetercyclyl radical;X and Y each independently represents hydrogen, optionally substituted lower alkyl, halogen, cyano, carboxy, lower alkoxycarbonyl or carbamoyl; andQ represents a diradical consisting of a linear chain of 8 to 14 carbon atoms, one or more of which may be replaced by heteroatoms, said chain being optionally substituted by inert substituents and one or more of said carbon or heteratom chain members optionally forming part of a ring structure.Type: GrantFiled: June 22, 1984Date of Patent: August 25, 1987Assignee: Epis S.A.Inventor: Jacob Bar-Tana
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Patent number: 4680307Abstract: A compound of the formula: ##STR1## wherein X.sup.1 is a free or an esterified carboxyl group, or a group of the formula: ##STR2## (R.sup.a and R.sup.b are each independently a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.3 -C.sub.7 cycloalkyl group, a benzyl group, a phenyl group, a phenyl group substituted with a halogen atom or a C.sub.1 -C.sub.4 alkyl group, or, when taken together with the adjacent nitrogen atom to which they are attached, they represent a 5 to 7 membered saturated heterocyclic group, Y.sup.1 is a group of the formula: ##STR3## (R.sup.6 is a hydrogen atom or C.sub.1 -C.sub.4 alkyl group), ##STR4## (R.sup.6 is as defined above), ##STR5## R.sup.1 is a hydrogen atom, a hydroxyl group or a protected hydroxyl group, R.sup.2 is a hydrogen atom or R.sup.1 and R.sup.2, when taken together, mean a shingle linkage to from a double bond between the carbon atoms which they are linked, R.sup.3 is a hydroxyl group or a protected hydroxyl group, R.sup.4 is a hydrogen atom or a C.sub.1 -C.sub.Type: GrantFiled: January 26, 1984Date of Patent: July 14, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Masami Muraoka, Toshio Nakamura, Akihiko Sugie, Keiichi Ono, Michihiro Yamamoto
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Patent number: 4652676Abstract: This invention relates to new novel sweeteners of the formula: ##STR1## wherein A is hydrogen, alkyl containing 1-3 carbon atoms or alkoxymethyl wherein the alkoxy contains 1-3 carbon atoms;A' is hydrogen or alkyl containing 1-3 carbon atoms;A and A' taken together with the carbon atom to which they are attached form cycloalkyl containing 3-4 carbon atoms;Y is --(CHR.sub.2).sub.n --R.sub.1, --CHR.sub.3 R.sub.4 or R.sub.5 ;R.sub.1 is cycloalkyl, cycloalkenyl, bicycloalkyl or bicycloalkenyl containing up to 7 ring carbon atoms and up to a total of 12 carbon atoms;R.sub.5 is alkyl containing up to 11 carbon atoms;R.sub.2 is H or alkyl containing 1-4 carbon atoms;R.sub.3 and R.sub.4 are each cycloalkyl containing 3-4 ring carbon atoms;n=0 or 1; andm=0 or 1;and food-acceptable salts thereof.Type: GrantFiled: May 6, 1985Date of Patent: March 24, 1987Assignee: General Foods CorporationInventors: Paul R. Zanno, Ronald E. Barnett, Glenn M. Roy
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Patent number: 4632997Abstract: A method for preparing a cis-bicyclo[3.3.0]octylidene derivative represented by the formula: ##STR1## wherein R.sup.1 is a hydrogen atom or an alkyl group; R.sup.2 is a hydrogen atom or a protective group for hydroxyl group; and Y is ##STR2## where R.sup.3 is a hydrogen atom or a protective group for hydroxyl group; R.sup.4 is a hydrogen atom or a straight, branched or cyclic alkyl group, alkenyl group or alkynyl group; and X is a group represented by CH.dbd.CH or C.tbd.C,comprises carrying out the catalytic hydrogenation reaction of a (1-alkenyl)-cis-bicyclo[3.3.0]octene derivative represented by the formula: ##STR3## wherein R.sup.1, R.sup.2 and Y have the same meanings as defined above, in the presence of a metal carbonyl compound or its complex represented by the formula:Mw(CO)x(H)y(R)zwherein M is a metal element of the group VIB; R is a .pi. ligand or a phosphine ligand; w is 1 or 2; x is an integer of 3 to 6; y is 0 or 1; and z is 0 or an integer of 1 to 3.Type: GrantFiled: February 8, 1985Date of Patent: December 30, 1986Assignee: Sagami Chemical Research CenterInventors: Masakatsu Shibasaki, Mikiko Sodeoka, Yuji Ogawa
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Patent number: 4552898Abstract: Compounds useful in treating cardiovascular disorders are the carboxylic acids depicted in formulas (1) and (2) ##STR1## as well as their pharmaceutically acceptable, non-toxic salts and esters, wherein:n is an integer from one to four;R.sub.1 is hydroxy;R.sub.2 is hydrogen; orR.sub.1 and R.sub.2 together are an oxo group;R.sub.3 is ##STR2## wherein A is --CH.sub.2 --CH.sub.2 --; trans--CH.dbd.CH--; --C.tbd.C--; andR.sub.4 is linear or branched alkyl of one to twelve carbons, preferably 1-10 carbons, most preferably 3-8 carbons, cycloalkyl of three to eight carbons; phenyl optionally substituted with one or two identical substituents selected from the group consisting of lower alkyl, lower alkoxy, hydroxy, trifluoromethyl, and halo; or phenylloweralkyl optionally substituted with one or two identical substituents selected from the group consisting of lower alkyl, lower alkoxy, hydroxy, trifluoromethyl, and halo.Type: GrantFiled: August 19, 1983Date of Patent: November 12, 1985Assignee: Syntex (U.S.A.) Inc.Inventors: Tsung-Tee Li, Michael Marx
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Patent number: 4537989Abstract: A compound of the formula ##STR1## wherein X.sup.1 is a free or an esterified carboxyl group, or a group of the formula: ##STR2## (R.sup.a and R.sup.b are each independently a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.3 -C.sub.7 cycloalkyl group, a benzyl group, a phenyl group, a phenyl group substituted with a halogen atom or a C.sub.1 -C.sub.4 alkyl group, or, when taken together with the adjacent nitrogen atom to which they are attached, they represent a 5 to 7 membered saturated heterocyclic group), Y is a group of the formula: ##STR3## (R.sup.6 is a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group) or ##STR4## (R.sup.6 is as defined above), R.sup.1 is a hydrogen atom, a hydroxyl group or a protected hydroxyl group, R.sup.2 is a hydrogen atom or R.sup.1 and R.sup.2, when taken together, mean a single linkage to form a double bond between the carbon atoms which they are linked, R.sup.3 is a hydroxyl group or a protected hydroxyl group, R.sup.4 is a hydrogen atom or a C.sub.1 -C.sub.Type: GrantFiled: April 15, 1983Date of Patent: August 27, 1985Assignee: Sumitomo Chemical Company, LimitedInventors: Keiichi Ono, Akihiko Sugie, Masami Muraoka, Michihiro Yamamoto
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Patent number: 4524213Abstract: A compound represented by the general formula: ##STR1## where each A is --OH or --OR where R is an alkyl group, an alkenyl group or a cycloalkyl group, or both A together represent a >O group.Type: GrantFiled: February 8, 1984Date of Patent: June 18, 1985Assignee: Nissan Chemical Industries Ltd.Inventors: Hideo Suzuki, Kanji Ohtsuka, Masami Adachi
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Patent number: 4517202Abstract: Prostaglandin analogues of the general formula: ##STR1## (wherein R.sup.1 represents a hydrogen atom or a straight- or branched-chain alkyl group, Y.sup.1 represents a carbonyl or hydroxymethylene group, represents a single or double bond, A.sup.1 represents an alkylene linkage containing 2 or 3 carbon atoms and optionally bearing a methyl or ethyl substituent, R.sup.2 represents a hydrogen atom or a methyl or ethyl group and R.sup.3 represents a hydrogen atom or else R.sup.2 and R.sup.3 form an alkylene linkage containing 2 or 3 carbon atoms, optionally bearing a methyl or ethyl substituent, such that the symbols A.sup.1, R.sup.2 and R.sup.3, together with the carbon atoms through which they are connected, form a cycloalkyl ring of 6, 7 or 8 carbon atoms, optionally bearing one or two methyl or ethyl substituents, X.sup.1 represents an ethylene or trans-vinylene group, Y.sup.2 represents a carbonyl or hydroxymethylene group, and either (i) A.sup.Type: GrantFiled: May 26, 1983Date of Patent: May 14, 1985Assignee: May & Baker LimitedInventors: Clive W. Bird, Helene I. Butler, Michael P. L. Caton, Edward C. J. Coffee, Geoffrey Darnbrough, Terance W. Hart
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Patent number: 4514396Abstract: 13, 14 didehydro-15 cyclic prostacyclins have been prepared.Type: GrantFiled: September 28, 1983Date of Patent: April 30, 1985Assignee: Farmitalia Carlo Erba S.p.A.Inventors: Nicola Mongelli, Carmelo Gandolfi
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Patent number: 4504671Abstract: Aldoxime or ketoxime-O-alkanoic acid is prepared by transoximation of an aldehyde or ketone, the reaction being conducted in a liquid phase at a pressure below one atmosphere. Conversion of the aldoxime or ketoxime-O-alkanoic acid to the ester or salt form is also described.Type: GrantFiled: October 15, 1982Date of Patent: March 12, 1985Assignee: PPG Industries, Inc.Inventors: Dennis K. Krass, John C. Crano, Melvin S. Newman
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Patent number: 4503072Abstract: Compounds of general structural formula: ##STR1## wherein Q is: ##STR2## or pharmaceutically acceptable salts, C.sub.1-3 alkyl esters or .alpha.-monoglyceride when Q is a dihydroxy acid are useful as antihypercholesterolemic agents for the treatment of atherosclerosis, familial hypercholesterolemia, hyperlipemia and like diseases. They also have useful antifungal activity.Type: GrantFiled: June 18, 1984Date of Patent: March 5, 1985Assignee: Merck & Co., Inc.Inventors: William F. Hoffman, Ta-Jyh Lee, Robert L. Smith, Alvin K. Willard
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Patent number: 4479966Abstract: Prostaglandin I.sub.2 analogues of the formula: ##STR1## [wherein the symbol between the carbon atoms in positions 5 and 6 represents a single or double bond, Y represents ethylene or trans-vinylene, R.sup.1 represents hydrogen, alkyl of 1 to 12 carbon atoms, aralkyl of 7 to 12 carbon atoms, cycloalkyl of 4 to 7 carbon atoms optionally substituted by alkyl of 1 to 4 carbon atoms, phenyl optionally substituted by chlorine, trifluoromethyl, alkyl of 1 to 4 carbon atoms or phenyl, a --C.sub.m H.sub.2m COOR.sup.7 group (wherein m represents an integer of from 1 to 12 and R.sup.7 represents alkyl of 1 to 4 carbon atoms), a --C.sub.n H.sub.2n OR.sup.8 group (wherein n represents an integer of from 2 to 12 and R.sup.8 represents hydrogen or alkyl of 1 to 4 carbon atoms) or a ##STR2## group (wherein R.sup.9 and R.sup.10 each represent alkyl of 1 to 4 carbon atoms and n is as hereinbefore defined), R.sup.2 represents hydrogen or a hydroxy-protecting group, R.sup.Type: GrantFiled: January 21, 1980Date of Patent: October 30, 1984Assignee: Ono Pharmaceutical Company, Ltd.Inventors: Masaki Hayashi, Yoshitaka Konishi, Yoshinobu Arai