Plural Alicyclic Rings Patents (Class 562/498)
  • Patent number: 5631291
    Abstract: The invention relates to cyclopentane- and -pentene-.beta.-amino acids, processes for their preparation and their use as medicaments.
    Type: Grant
    Filed: November 9, 1994
    Date of Patent: May 20, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Joachim Mittendorf, Franz Kunisch, Michael Matzke, Hans-Christian Militzer, Rainer Endermann, Karl G. Metzger, Klaus-Dieter Bremm, Manfred Plempel
  • Patent number: 5576355
    Abstract: 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: Grant
    Filed: December 15, 1993
    Date of Patent: November 19, 1996
    Assignee: Mobil Oil Corp.
    Inventors: Catherine S. H. Chen, Dong-ming Shen
  • Patent number: 5561124
    Abstract: 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: Grant
    Filed: May 17, 1995
    Date of Patent: October 1, 1996
    Inventor: Robert L. Webb
  • Patent number: 5449684
    Abstract: 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: Grant
    Filed: February 3, 1994
    Date of Patent: September 12, 1995
    Assignee: PharmaMar, S.A.
    Inventors: Jun-Ichi Tanaka, Tatsuo Higa, Khanit Suwanoborirux, C. W. Jefford, G. Bernardinelli, Dolores G. Gravalos
  • Patent number: 5393924
    Abstract: 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: Grant
    Filed: April 29, 1994
    Date of Patent: February 28, 1995
    Assignee: Hoechst Celanese Corporation
    Inventors: Ahmed M. Tafesh, Olan S. Fruchey, Charles B. Hilton
  • Patent number: 5374654
    Abstract: 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: Grant
    Filed: April 21, 1993
    Date of Patent: December 20, 1994
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbruggen, Ulrich Klar, Bob Nieuweboer, Claus-Steffen Sturzebecher
  • Patent number: 5264586
    Abstract: Chimeric analogs of calicheamicin that include an analog of calicheamicinone linked to an ester or glycoside, (-)-calicheamicinone and its analogs are disclosed.
    Type: Grant
    Filed: July 16, 1992
    Date of Patent: November 23, 1993
    Assignee: The Scripps Research Institute
    Inventors: Kyriacos C. Nicolaou, Adrian L. Smith, Chan-Kou Hwang, Emmanuel Pitsinos
  • Patent number: 5248807
    Abstract: 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: Grant
    Filed: July 8, 1992
    Date of Patent: September 28, 1993
    Assignee: Shionogi & Co., Ltd.
    Inventors: Masafumi Fujimoto, Kensuke Sakurai, Shinichi Mihara, Miharu Nakamura, Toshiro Konoike
  • Patent number: 5235119
    Abstract: 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: Grant
    Filed: October 1, 1992
    Date of Patent: August 10, 1993
    Assignee: The United States of America as represented by the Secretary of the Army
    Inventor: Abdollah Bashir-Hashemi
  • Patent number: 5232836
    Abstract: 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: Grant
    Filed: February 18, 1992
    Date of Patent: August 3, 1993
    Assignee: Ire-Medgenix S.A.
    Inventors: Roger Bouillon, Pierre J. De Clerco, Pierre Eliard, Maurits Vanderwalle
  • Patent number: 5214221
    Abstract: 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: Grant
    Filed: October 1, 1992
    Date of Patent: May 25, 1993
    Assignee: The United States of America as represented by the Secretary of the Army
    Inventor: Abdollah Bashir-Hashemi
  • Patent number: 5206416
    Abstract: 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: Grant
    Filed: September 24, 1991
    Date of Patent: April 27, 1993
    Assignee: Teijin Limited
    Inventor: Seizi Kurozumi
  • Patent number: 5192798
    Abstract: 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: Grant
    Filed: August 16, 1990
    Date of Patent: March 9, 1993
    Assignee: The Upjohn Company
    Inventors: James W. Aiken, Charles H. Spilman, Edward W. Thomas
  • Patent number: 5190964
    Abstract: 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: Grant
    Filed: February 15, 1990
    Date of Patent: March 2, 1993
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Martin Haberey, Claus-Steffen Sturzebecher, Michael-Harold Town
  • Patent number: 5162353
    Abstract: 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: Grant
    Filed: August 21, 1990
    Date of Patent: November 10, 1992
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbrueggen, Bob Nieuweboer, Claus-Steffen Stuerzebecher
  • Patent number: 5159102
    Abstract: 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: Grant
    Filed: May 22, 1990
    Date of Patent: October 27, 1992
    Assignee: Teijin Limited
    Inventors: Toshio Tanaka, Kiyoshi Bannai, Atsuo Hazato, Seizi Kurozumi
  • Patent number: 5124343
    Abstract: 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: Grant
    Filed: January 6, 1988
    Date of Patent: June 23, 1992
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbrueggen, Hernd Raduechel, Werner Skuballa, Norbert Schwarz, Jorge Casals-Stenzel, Gerda Mannesmann, Michael H. Town
  • Patent number: 5109021
    Abstract: 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: Grant
    Filed: May 25, 1990
    Date of Patent: April 28, 1992
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Katsuhiro Imaki, Hajimu Miyake, Tadao Okegawa
  • Patent number: 5100917
    Abstract: 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: Grant
    Filed: September 11, 1990
    Date of Patent: March 31, 1992
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Gary A. Flynn, Philippe Bey, Thomas R. Blohm
  • Patent number: 5093519
    Abstract: 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: Grant
    Filed: May 1, 1989
    Date of Patent: March 3, 1992
    Assignee: Ire-Medgenix S.A.
    Inventors: Roger Bouillon, Pierre J. De Clercq, Pierre Eliard, Maurits Vandewalle
  • Patent number: 5084592
    Abstract: 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: Grant
    Filed: September 30, 1988
    Date of Patent: January 28, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Schrott, Peter Neumann, Sibylle Brosius, Helmut Barzynski, Klaus D. Schomann, Harald Kuppelmaier
  • Patent number: 5036104
    Abstract: 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: Grant
    Filed: June 14, 1990
    Date of Patent: July 30, 1991
    Assignee: Pfizer Inc.
    Inventors: John C. Danilewicz, Keith James
  • Patent number: 4983627
    Abstract: 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: Grant
    Filed: November 10, 1988
    Date of Patent: January 8, 1991
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Counde O'Yang, Walter Kurz, Keith A. M. Walker, Helen Y. Wu
  • Patent number: 4971987
    Abstract: 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: Grant
    Filed: March 7, 1988
    Date of Patent: November 20, 1990
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbrueggen, Bob Nieuweboer, Claus-Steffen Stuerzebecher, Ulrich Klar
  • Patent number: 4963585
    Abstract: 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: Grant
    Filed: February 14, 1989
    Date of Patent: October 16, 1990
    Assignee: Fujisawa Pharmaceutical Company, Ltd.
    Inventors: Masanori Okamoto, Eisaku Tsujii, Tsutomu Kaizu, Hiroshi Hatanaka, Masakuni Okuhara, Kozo Sawada, Hirokazu Tanaka
  • Patent number: 4954524
    Abstract: 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: Grant
    Filed: April 6, 1989
    Date of Patent: September 4, 1990
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Jorge Casals-Stenzel, Gerda Mannesmann, Ekkehard Schillinger, Michael H. Town
  • Patent number: 4894181
    Abstract: 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: Grant
    Filed: May 16, 1988
    Date of Patent: January 16, 1990
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Klaus Praefcke, Bernd Kohne, Eike Poetsch
  • Patent number: 4833271
    Abstract: 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: Grant
    Filed: August 23, 1985
    Date of Patent: May 23, 1989
    Inventor: George L. Nelson
  • Patent number: 4824999
    Abstract: 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: Grant
    Filed: September 23, 1988
    Date of Patent: April 25, 1989
    Assignee: American Home Products Corporation
    Inventor: Gary P. Stack
  • Patent number: 4797488
    Abstract: 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: Grant
    Filed: April 3, 1987
    Date of Patent: January 10, 1989
    Assignee: American Home Products Corporation
    Inventors: Gary P. Stack, Thomas D. Golobish, Magid A. Abou-Gharbia
  • Patent number: 4792550
    Abstract: 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: Grant
    Filed: June 11, 1985
    Date of Patent: December 20, 1988
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Hajimu Miyake, Tadao Okegawa, Akiyoshi Kawasaki
  • Patent number: 4788332
    Abstract: Sweeteners of the formula: ##STR1## and food-acceptable salts thereof, where the substituents are disclosed herein.
    Type: Grant
    Filed: January 19, 1988
    Date of Patent: November 29, 1988
    Assignee: General Foods Corporation
    Inventors: Paul R. Zanno, Ronald E. Barnett, Glenn M. Roy
  • Patent number: 4764528
    Abstract: 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: Grant
    Filed: March 10, 1987
    Date of Patent: August 16, 1988
    Assignee: Teruo Kabushiki Kaisha
    Inventors: Keiko Chiba, Makoto Takai, Toshio Wakabayashi
  • Patent number: 4735966
    Abstract: 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: Grant
    Filed: August 25, 1986
    Date of Patent: April 5, 1988
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Helen Y. Wu, Walter Kurz
  • Patent number: 4708963
    Abstract: 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: Grant
    Filed: May 28, 1985
    Date of Patent: November 24, 1987
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduchel, Norbert Schwarz, Helmut Vorbruggen, Jorge Casals-Stenzel, Ekkehard Schillinger, Michael H. Town
  • Patent number: 4701552
    Abstract: 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: Grant
    Filed: March 21, 1986
    Date of Patent: October 20, 1987
    Assignee: General Foods Corporation
    Inventors: Paul R. Zanno, Ronald E. Barnett, Glenn M. Roy
  • Patent number: 4698363
    Abstract: 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: Grant
    Filed: November 20, 1985
    Date of Patent: October 6, 1987
    Assignee: May & Baker Limited
    Inventor: Terance W. Hart
  • Patent number: 4692464
    Abstract: 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: Grant
    Filed: February 26, 1982
    Date of Patent: September 8, 1987
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Gerda Mannesmann, Wolfgang Losert, Jorge Casals
  • Patent number: 4689344
    Abstract: 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: Grant
    Filed: June 22, 1984
    Date of Patent: August 25, 1987
    Assignee: Epis S.A.
    Inventor: Jacob Bar-Tana
  • Patent number: 4680307
    Abstract: 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: Grant
    Filed: January 26, 1984
    Date of Patent: July 14, 1987
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masami Muraoka, Toshio Nakamura, Akihiko Sugie, Keiichi Ono, Michihiro Yamamoto
  • Patent number: 4652676
    Abstract: 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: Grant
    Filed: May 6, 1985
    Date of Patent: March 24, 1987
    Assignee: General Foods Corporation
    Inventors: Paul R. Zanno, Ronald E. Barnett, Glenn M. Roy
  • Patent number: 4632997
    Abstract: 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: Grant
    Filed: February 8, 1985
    Date of Patent: December 30, 1986
    Assignee: Sagami Chemical Research Center
    Inventors: Masakatsu Shibasaki, Mikiko Sodeoka, Yuji Ogawa
  • Patent number: 4552898
    Abstract: 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: Grant
    Filed: August 19, 1983
    Date of Patent: November 12, 1985
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Tsung-Tee Li, Michael Marx
  • Patent number: 4537989
    Abstract: 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: Grant
    Filed: April 15, 1983
    Date of Patent: August 27, 1985
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Keiichi Ono, Akihiko Sugie, Masami Muraoka, Michihiro Yamamoto
  • Patent number: 4524213
    Abstract: 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: Grant
    Filed: February 8, 1984
    Date of Patent: June 18, 1985
    Assignee: Nissan Chemical Industries Ltd.
    Inventors: Hideo Suzuki, Kanji Ohtsuka, Masami Adachi
  • Patent number: 4517202
    Abstract: 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: Grant
    Filed: May 26, 1983
    Date of Patent: May 14, 1985
    Assignee: May & Baker Limited
    Inventors: Clive W. Bird, Helene I. Butler, Michael P. L. Caton, Edward C. J. Coffee, Geoffrey Darnbrough, Terance W. Hart
  • Patent number: 4514396
    Abstract: 13, 14 didehydro-15 cyclic prostacyclins have been prepared.
    Type: Grant
    Filed: September 28, 1983
    Date of Patent: April 30, 1985
    Assignee: Farmitalia Carlo Erba S.p.A.
    Inventors: Nicola Mongelli, Carmelo Gandolfi
  • Patent number: 4504671
    Abstract: 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: Grant
    Filed: October 15, 1982
    Date of Patent: March 12, 1985
    Assignee: PPG Industries, Inc.
    Inventors: Dennis K. Krass, John C. Crano, Melvin S. Newman
  • Patent number: 4503072
    Abstract: 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: Grant
    Filed: June 18, 1984
    Date of Patent: March 5, 1985
    Assignee: Merck & Co., Inc.
    Inventors: William F. Hoffman, Ta-Jyh Lee, Robert L. Smith, Alvin K. Willard
  • Patent number: 4479966
    Abstract: 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: Grant
    Filed: January 21, 1980
    Date of Patent: October 30, 1984
    Assignee: Ono Pharmaceutical Company, Ltd.
    Inventors: Masaki Hayashi, Yoshitaka Konishi, Yoshinobu Arai