Orthofused Patents (Class 562/501)
  • Patent number: 6576786
    Abstract: The invention relates to a process for preparing substituted cyclopentane derivatives represented by the formula (I) wherein R1, R2, R3, R4, X and Y are as described in the specification, and pharmaceutically acceptable salts thereof. The invention further relates to a process for purifying the compound of formula (Ia) and novel crystalline forms of the compound of formula (Ia).
    Type: Grant
    Filed: November 26, 2001
    Date of Patent: June 10, 2003
    Assignee: Biocryst Pharmaceuticals Inc.
    Inventors: Ahmed F. Abdel-Magid, Hans-Ulrich Bichsel, Daniel J. Korey, Gunther G. Laufer, Erja A. Lehto, Sebastiano Mattei, Max Rey, Thomas W. Schultz, Cynthia Maryanoff
  • Publication number: 20030078300
    Abstract: The compounds of the instant invention are bicyclic or tricyclic amino acids useful in the treatment of epilepsy, faintness attacks, hypokinesia, cranial disorders, neurodegenerative disorders, depression, anxiety, panic, pain, arthritis, neuropathological disorders, sleep disorders, visceral pain disorders, and gastrointestinal disorders. Processes for the preparation of the final products and intermediates useful in the process are included. Pharmaceutical compositions containing one or more of the compounds are also included.
    Type: Application
    Filed: April 16, 2002
    Publication date: April 24, 2003
    Applicant: Pfizer Inc.
    Inventors: David Clive Blakemore, Justin Stephen Bryans, Sophie Caroline Williams
  • Patent number: 6541515
    Abstract: Compounds useful in the inhibition of HIV integrase, the prevention or treatment of infection by HIV and the treatment of AIDS, either as compounds, pharmaceutically acceptable salts, pharmaceutical composition ingredients, whether or not in combination with other antivirals, immunomodulators, antibiotics or vaccines are described. Methods of treating AIDS and methods of preventing or treating infection by HIV are also described. The culture Cytospora sp. MF 6608 (ATCC PTA-1691) is also disclosed, as well as processes for making a compound of the present invention employing the culture.
    Type: Grant
    Filed: August 9, 2001
    Date of Patent: April 1, 2003
    Assignee: Merck & Co., Inc.
    Inventors: Sheo Bux Singh, Hiranthi Jayasuriya, Ziqiang Guan, Keith C. Silverman, Russell B. Lingham, Anne W. Dombrowski, Daria J. Hazuda, Jon D. Polishook
  • Patent number: 6506929
    Abstract: A process is disclosed for the preparation of simvastatin which enables highly regio selective C-methylation of the 2′-position group of lovastatin without requiring protection/deprotection of 13-OH of lovastatin and lactone ring opening/closure.
    Type: Grant
    Filed: April 24, 2001
    Date of Patent: January 14, 2003
    Assignee: Apotex Inc.
    Inventors: Khashayar Karimian, Tim Fat Tam, Yong Tao, Yiwei Li, Gary Doucette
  • Publication number: 20020072607
    Abstract: Enamide derivatives of formula (1) are described: 1
    Type: Application
    Filed: September 5, 2001
    Publication date: June 13, 2002
    Inventors: Timothy John Norman, John Robert Porter, John Clifford Head, Andrew James Ratcliffe
  • Patent number: 6392104
    Abstract: In the presence of an imide compound (e.g., N-hydroxyphthalimide) shown by the formula (2): wherein R1 and R2 independently represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a cycloalkyl group; or R1 and R2 may bond together to form a double bond or an aromatic or non-aromatic ring; Y is O or OH and n=1 to 3; or the imide compound and a co-catalyst (e.g., a transition metal compound), an adamantane derivative having a functional group such as a nitro group, an amino group, a hydroxyl group, a carboxyl group, a hydroxymethyl group and an isocyanato group is oxidized with oxygen. According to the above method, an adamantane derivative having a hydroxyl group together with a functional group such as a nitro group, an amino group, a hydroxyl group, a carboxyl group, a hydroxymethyl group and an isocyanato group is efficiently obtained.
    Type: Grant
    Filed: November 10, 1998
    Date of Patent: May 21, 2002
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Yasutaka Ishii, Tatsuya Nakano, Naruhisa Hirai
  • Patent number: 6392086
    Abstract: The present inventions relate to a (1S,5R,6S)- or (1SR, 5RS, 6SR)-3-fluoro-2-oxobicyclo[3.1.0]hex-3-ene-6-carboxylic acid derivative represented by Formula (1): [in the formula, R represents OR1 or NR1R2, wherein R1 and R2 are identical or different, and each represents a hydrogen atom, a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a (C3-C6 cycloalkyl) (C1-C6 alkyl) group, an aryl group, an aryl (C1-C6 alkyl) group, a (C1-C6 alkoxy) (C1-C6 alkyl) group, a C1-C6 hydroxyalkyl group, a (C1-C6 alkylthio) (C1-C6 alkyl) group, or a C1-C6 mercaptoalkyl group], and a process for producing the same, and a process for efficiently producing a fluorine-containing amino acid compound acting on group 2 metabotropic glutamate receptors, which has treatment effects or prevention effects on psychiatric diseases or neurological diseases, characterized by hydrogenating the derivative, and subsequently, subjecting it to hydantoination or aminocyanidation, followed by hydrolysis.
    Type: Grant
    Filed: June 7, 2001
    Date of Patent: May 21, 2002
    Assignee: Taisho Pharmaceutical Co., Ltd.
    Inventors: Atsuro Nakazato, Toshihito Kumagai, Kazunari Sakagami, Kazuyuki Tomisawa, Hisanako Ito, Takeo Taguchi
  • Patent number: 6326369
    Abstract: A compound of the formula: wherein R1 and R2 each represents a lower alkyl, or R1 and R2 may be bonded together to form a ring; X represents a spacer of which the number of atoms constituting the principal chain is 1 to 15; Y represents an acyl, or a hydroxy, an amino or an aromatic group, each of which may be substituted; and ring A represents a 5- to 8-membered ring which may be further substituted apart from —X—Y, or a salt thereof is useful as a pharmaceutical composition for preventing or treating disease related to mitochondrial dysfunction.
    Type: Grant
    Filed: July 6, 1999
    Date of Patent: December 4, 2001
    Assignee: Takeda Chemicals Industries, Ltd.
    Inventors: Kaneyoshi Kato, Taiichi Ohra, Masaomi Miyamoto
  • Patent number: 6316498
    Abstract: Fluorine-containing amino acid derivatives represented general formula (I), pharmaceutically acceptable salts thereof or hydrates of the same, wherein X1 represents hydrogen or fluorine; and R1 and R2 are the same or different and each represents hydrogen or lower C1-10 alkyl. These compounds are useful as drugs, in particular, group 2 metabotropic glutamate receptor agonists for treating and preventing psychiatric disorders such as schizophrenia, anxiety and associated diseases, depression, bipolar disturbance and epilepsy, and neurological diseases such as drug addiction, cognition disorder, Alzheimer's disease, Huntington's chorea, Parkinson's disease, motility disturbance associating muscular stiffness, cerebral ischemia, cerebral insufficiency, spinal cord lesion and head disturbance.
    Type: Grant
    Filed: July 27, 2000
    Date of Patent: November 13, 2001
    Assignee: Taisho Pharmaceutical Co., Ltd.
    Inventors: Atsuro Nakazato, Toshihito Kumagai, Kazunari Sakagami, Kazuyuki Tomisawa
  • Patent number: 6204292
    Abstract: The present invention provides bicyclic metabotropic glutamate receptor ligands, as well as compositions comprising such ligands, and and methods for their use.
    Type: Grant
    Filed: July 17, 1998
    Date of Patent: March 20, 2001
    Assignee: Georgetown University
    Inventors: Alan P. Kozikowski, Darryl Hugh Steensma, Werner Tueckmantel, Gian Luca Araldi
  • Patent number: 6177586
    Abstract: The starting materials for a production process of a vitamin D3 derivative are disclosed, e.g., a cyclopentene derivative represented by the formula (1-2): wherein R11 is a hydrogen atom, tri(C1 to C7 hydrocarbon) silyl group, C2 to C7 acyl group, group forming an acetal bond together with an oxygen atom of a hydroxyl group, and X1 is a bromine or iodine atom; and a heptanoic acid derivative represented by the formula (2-4): wherein X2 is a bromine atom or iodine atom.
    Type: Grant
    Filed: June 8, 1999
    Date of Patent: January 23, 2001
    Assignee: Teijin Limited
    Inventors: Masayasu Tabe, Atsuo Hazato, Kenji Manabe, Qinqzhi Gao, Hiroko Tanaka
  • Patent number: 6160009
    Abstract: Compounds of the formula ##STR1## in which R.sup.1 and R.sup.2 are as defined in the specification, and non-toxic metabolically labile ester and amides thereof are useful as modulators of metabotropic glutamate receptor function.
    Type: Grant
    Filed: May 28, 1999
    Date of Patent: December 12, 2000
    Assignee: Eli Lilly and Company
    Inventors: Steven Marc Massey, James Allen Monn, Matthew John Valli
  • Patent number: 6143783
    Abstract: The present invention relates to compounds of the formula ##STR1## in which R.sup.1 is defined in the specification, and non-toxic metabolically labile esters and amides thereof are useful as modulators of metabotropic glutamate receptor function.
    Type: Grant
    Filed: November 11, 1999
    Date of Patent: November 7, 2000
    Assignee: Eli Lilly and Company
    Inventors: James Allen Monn, Matthew John Valli
  • Patent number: 6107342
    Abstract: The present invention relates to the compound of formulae ##STR1## and to a process for the manufacture of compounds of the general formula ##STR2## which are ligands for the metabotropic glutamate receptors of group II, whereinT is tritium;R.sup.1 is hydroxy, lower alkoxy, lower alkenyloxy, benzyloxy, hydrogen, deuterium or tritium;R.sup.11 is hydrogen, deuterium or tritium, hydroxy or amino, andR.sup.2 is hydrogen or tritium, orR.sup.1 and R.sup.2 form a bond.
    Type: Grant
    Filed: August 30, 1999
    Date of Patent: August 22, 2000
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Geo Adam, Philippe Nicolas Huguenin-Virchaux, Vincent Mutel, Heinz Stadler, Thomas Johannes Woltering
  • Patent number: 5958960
    Abstract: Compounds of the formula ##STR1## in which R.sup.1 and R.sup.2 are as defined in the specification, and non-toxic metabolically labile ester and amides thereof are useful as modulators of metabotropic glutamate receptor function.
    Type: Grant
    Filed: May 13, 1998
    Date of Patent: September 28, 1999
    Assignee: Eli Lilly and Company
    Inventors: Steven Marc Massey, James Allen Monn, Matthew John Valli
  • Patent number: 5925782
    Abstract: The present invention provides novel compounds that affect certain excitatory amino acid receptors, and are useful in the treatment of neurological disorders and psychiatric disorders.
    Type: Grant
    Filed: May 5, 1997
    Date of Patent: July 20, 1999
    Assignee: Eli Lilly and Company
    Inventor: James A. Monn
  • Patent number: 5916920
    Abstract: Compounds of the formula ##STR1## in which X represents a bond, S, O or NR.sup.a ; and R is as defined in the specification are useful as modulators of metabotropic glutamate receptor function.
    Type: Grant
    Filed: November 14, 1996
    Date of Patent: June 29, 1999
    Assignee: Eli Lilly and Company
    Inventors: Carmen Dominguez Fernandez, David Reed Helton, Steven Marc Massey, James Allen Monn
  • Patent number: 5780676
    Abstract: Compounds, compositions, and methods for modulating processes mediated by Retinoid X Receptors using retinoid-like compounds which have activity selective for members of the subclass of Retinoid X Receptors (RXRs), in preference to members of the subclass of Retinoic Acid Receptors (RARs). Examples of such compounds are bicyclic benzyl, pyridinyl, thiophene, furanyl, pyrrole, and poiyenoic acid derivatives including carbocyclic polyenoic acids. The disclosed methods employ compounds for modulating processes selectively mediated by Retinoid X Receptors.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: July 14, 1998
    Assignee: Ligand Pharmaceuticals Incorporated
    Inventors: Marcus F. Boehm, Richard A. Heyman, Lin Zhi, Chan Kou Hwang, Steve White, Alex Nadzan
  • Patent number: 5750566
    Abstract: The present invention provides novel compounds that affect certain excitatory amino acid receptors, and are useful in the treatment of neurological disorders and psychiatric disorders.
    Type: Grant
    Filed: June 29, 1995
    Date of Patent: May 12, 1998
    Assignee: Eli Lilly and Company
    Inventors: James A. Monn, Darryle D. Schoepp
  • Patent number: 5739160
    Abstract: New Cyclopentane- or cyclopentene-beta-aminoacid derivatives and their isomers, acid additional salts and metal salt complexes have strong antimicrobial and broad-spectrum antimycotic acitivity. As antimycotics they are especially active against dermatophyte, and biphasic fungi. The new compounds are also low toxicity antibacterial agents, effective against Gram positive bacteria, including antibiotic-resistant strains. The new Cyclopentane- or cyclopentene-beta-aminoacid derivatives are useful in human or veterinary medicine for combating dermatomycosis or systemic mycosis or local or systemic bacterial infections. In addition, the new compounds can also be used as preservatives, especially for water, foods, or organic materials such as polymers, lubricants, paints, fibers, leather, paper or wood.
    Type: Grant
    Filed: September 19, 1994
    Date of Patent: April 14, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Joachim Mittendorf, Franz Kunisch, Michael Matzke, Hans-Christian Militzer, Rainer Endermann, Karl Georg Metzger, Klaus-Dieter Bremm, Manfred Plempel
  • Patent number: 5726320
    Abstract: A process for the preparation of (+)-2-amino-bicyclo?3.1.0!-hexane-2-6-dicarboxylic acid, or a pharmaceutically acceptable salt thereof, which comprises hydrolysing (-)-2-spiro-5'-hydantoinbicyclo?3.1.0!hexane-6-carboxylic acid or a salt thereof, and optionally forming a pharmaceutically acceptable salt. Also disclosed are intermediates useful in the process.
    Type: Grant
    Filed: June 26, 1996
    Date of Patent: March 10, 1998
    Assignee: Eli Lilly and Company
    Inventor: Roger Lewis Robey
  • Patent number: 5723494
    Abstract: Compounds represented by general formula (I) and (II), in which r is 1 or 2, R.sub.2 and R.sub.3 are selected independently from H, CH.sub.3, C.sub.2 H.sub.5 and CHO, provided that R.sub.2 and R.sub.3 are not simultaneously CHO, and in which R.sub.1 is selected from: an aminoalkyl adamantyl group, a monocyclic aminoalkyl group, a dicyclic aminospiro group, a dicyclic amino group (orthofused), a dicyclic amino group, and azacycloalkyl group, an azadicyclic group (orthofused), a dicyclic azaspiro group, and azadicyclic group, and azacycloalkyl group, and a linear or branched aminoalkyl group.
    Type: Grant
    Filed: September 11, 1995
    Date of Patent: March 3, 1998
    Assignee: Rotta Research Laboratorium S.P.A.
    Inventors: Francesco Makovec, Walter Peris, Lucio C. Rovati, Luigi A. Rovati
  • Patent number: 5700833
    Abstract: The present invention provides novel isocarbacyclin derivatives useful for search and study of prostacyclin receptor and as a therapeutic drug for central nervous system diseases, which derivatives are expressed by the following formula ?I!: ##STR1## ?where, R.sup.1 represents a hydrogen atom, an alkyl group, or cation of an appropriate amount, and R.sup.2 an alkylene group.
    Type: Grant
    Filed: January 31, 1996
    Date of Patent: December 23, 1997
    Assignees: Research Developement Corporation of Japan, Atsuo Hazato
    Inventors: Yasuyoshi Watanabe, Masaaki Suzuki, Atsuo Hazato, Bengt Langstrom
  • Patent number: 5532408
    Abstract: Provided are .alpha.-chain-modified isocarbacyclins of which the .alpha.-chain is modified with a phenylene group, a cycloalkylene group or a thiophendiyl group, and these .alpha.-chain-modified isocarbacyclins show the activity for inhibiting the DNA synthesis of human smooth muscle cell and are expected to be capable of inhibiting the hypertrophy of a blood vessel.
    Type: Grant
    Filed: April 5, 1995
    Date of Patent: July 2, 1996
    Assignee: Teijin Limited
    Inventors: Masahiro Koga, Toshio Tanaka, Takao Fujii, Tsukio Masegi
  • Patent number: 5489613
    Abstract: Compounds of formula (I): ##STR1## have valuable platelet-aggregation inhibitory activities and may be used for the prophylaxis and treatment of such diseases as thrombosis.
    Type: Grant
    Filed: January 21, 1992
    Date of Patent: February 6, 1996
    Assignee: Sankyo Company, Limited
    Inventors: Kazuo Koyama, Shigeo Amemiya, Koichi Kojima, Shinsaku Kobayashi
  • 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: 5405870
    Abstract: Compounds of formula (Ic): ##STR1## having valuable platelet-aggregation inhibitory activities useful for the prophylaxis and treatment of such diseases as thrombosis and pharmaceutical compositions containing said compounds.
    Type: Grant
    Filed: November 4, 1993
    Date of Patent: April 11, 1995
    Assignee: Sankyo Company, Limited
    Inventors: Kazuo Koyama, Shigeo Amemiya, Koichi Kojima, Shinsaku Kobayashi
  • 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: 5347048
    Abstract: A process for producing (.+-.)-2,2,2,5a-tetramethyl-1-(carboxymethyl)-2-hydroxydecalin, comprising the steps of allowing a carbonate of dihydro-.beta.-vinyl-ionol to react with carbon monoxide in the presence of a palladium catalyst to form .beta.-monocyclohomofarnesic acid, cyclizing said .beta.-monocyclohomofarnesic acid in the presence of an acid catalyst to form (.+-.)-norambreinolid, and hydrolyzing said (.+-.)-norambreinolide to form (.+-.)-2,5,5,8a-tetramethyl-1-(carboxymethyl)-2-hydroxydecalin.
    Type: Grant
    Filed: September 7, 1993
    Date of Patent: September 13, 1994
    Assignee: Kuraray Co., Ltd.
    Inventors: Goro Asanuma, Yoshin Tamai
  • Patent number: 5294616
    Abstract: A series of non-peptide derivatives that are antagonists of the fibrinogen IIb/IIIa receptor and thus are platelet aggregation compounds useful in the prevention and treatment of diseases caused by thrombus formation.
    Type: Grant
    Filed: March 25, 1992
    Date of Patent: March 15, 1994
    Assignee: Merck & Co., Inc.
    Inventors: Mark E. Duggan, Melissa S. Egbertson, Wasyl Halczenko, George D. Hartman, Laura M. Turchi, William L. Laswell
  • Patent number: 5290955
    Abstract: (-)-2,5,5,8a-Tetramethyl-1-(carboxymethyl)-2-hydroxydecalin is subjected to lactonization by dehydration to form decahydro-3a,6,6,9a-tetramethyl(3a.alpha.,5a.beta.,9a.alpha.,9b.beta.)-(+) -naphtho[2,1-b]furan-2(1H)-one, which is then reduced with a metal hydride to convert it into (-)-2,5,5,8a-tetramethyl-1-(carboxymethyl)-2-hydroxydecalin, followed by dehydrative cyclization to give L-ambrox.The (-)-2,5,5,8a-tetramethyl-1-(carboxymethyl)-2-hydroxydecalin is produced from its racemic mixture. The resolution is performed using a 1-(aryl)ethylamine. The starting material for the synthesis is beta-ionone.
    Type: Grant
    Filed: December 23, 1992
    Date of Patent: March 1, 1994
    Assignee: Kuraray Co., Ltd.
    Inventors: Goro Asanuma, Yoshin Tamai
  • Patent number: 5288878
    Abstract: The invention concerns a process for preparing (1S,2S,3R,5R)-2-[(3S)-2-halo-3-hydroxy-1-alken(ynyl)]-3-trialkylsilyloxy-7 ,7-(2,2-dimethyltrimethylenedioxy)-bicyclo[3.3.0]octane compounds of general Formula I ##STR1## wherein X is chlorine or bromine,R.sub.1 can mean straight-chain or branched alkyl of up to 6 carbon atoms, straight-chain or branched alkenyl of up to 6 carbon atoms, straight-chain or branched alkynyl of up to 6 carbon atoms,R.sub.2, R.sub.3, R.sub.4 can be in each case identical or different and can mean C.sub.1 -C.sub.4 -alkyl and phenyl optionally substituted by C.sub.1 -C.sub.4 -alkyl groups, wherein the 13,14-double bond has the trans configuration with respect to the C chain, by stereoselective reduction of an .alpha.-halo-enone of general Formula II ##STR2## wherein X, R.sub.1, R.sub.2, R.sub.3, R.sub.4 have the meanings given above,with a reagent produced from diisobutyl aluminum hydride and 2,6-di-tert-butyl-4-methylphenol.
    Type: Grant
    Filed: June 12, 1991
    Date of Patent: February 22, 1994
    Assignee: Schering Aktiengesellschaft
    Inventors: Michael Harre, Jurgen Westermann
  • Patent number: 5276177
    Abstract: A novel physiologically active substance is represented by the formula. ##STR1## The substance is preferably derived from propolis, has excellent antitumor activity and is useful as an antitumor drug.
    Type: Grant
    Filed: June 17, 1992
    Date of Patent: January 4, 1994
    Assignees: Tetsuya Matsuno, MPI Limited
    Inventors: Mayumi Yoshida, Yutaka Saito, Tetsuya Matsuno
  • Patent number: 5264455
    Abstract: X is hydrogen or --S(O).sub.m --R.sup.1 and Y is hydrogen or S(O).sub.n --R.sup.2, except that X and Y are not both hydrogen, or one of X and Y is --S--alkyl--SH and the other is hydrogen; ##STR2## and the remaining symbols are as defined in the specification.
    Type: Grant
    Filed: July 1, 1991
    Date of Patent: November 23, 1993
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Ravi K. Varma, Jeffrey O. Saunders, Sam T. Chao, Eric M. Gordon, Dinos P. Santafianos
  • 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: 5200530
    Abstract: The invention relates to a new process for the reduction of 15-keto carbacyclin intermediates in the presence of cerium(III) Salts.
    Type: Grant
    Filed: July 31, 1991
    Date of Patent: April 6, 1993
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Dahl, Gabriela Buttner, Dieter Peschel
  • Patent number: 5191115
    Abstract: To produce a carboxylic acid R.sup.1 --COOH, in which R.sup.1 is a tertiary branched alkyl residue or a cycloalkyl residue with one or more rings, which may be attached, and possibly substituted by at least one alkyl residue, the alpha carbon atom of the carbonyl group being a tertiary carbon atom, a branched or cyclic alkane R.sup.1 H, in which R.sup.1 is a branched alkyl residue or a cycloalkyl residue with one or more rings, which may be attached, and possibly substituted by at least one alkyl residue, the alpha carbon atom of the hydrogen atom being a tertiary carbon atom or a secondary carbon atom capable of being rearranged during reaction to a tertiary atom, is reacted in the presence of an acid catalyst with a formiate H(CO)O(CR.sup.2 R.sup.3 R.sup.4), in which R.sup.2, R.sup.3 and R.sup.4 denote hydrogen or alkyl, under the three following conditions: that R.sup.2, R.sup.3 and R.sup.
    Type: Grant
    Filed: February 5, 1991
    Date of Patent: March 2, 1993
    Assignee: Atochem
    Inventors: Veronique Lazzeri, Roger Gallo, Rachid Jalal
  • 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: 5157042
    Abstract: Carbacyclin derivatives of Formula I ##STR1## wherein R.sub.1 is 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 ;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; or a branched, saturated or straight-chain or branched, unsaturated aliphatic group of 2-10 carbon atoms; all of which are substituted by fluorine atoms;n 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 is hydrogen or alkyl of 1-5 carbon atoms and R.sub.7 is hydrogen, halogen or alkyl of 1-5 carbon atoms;R.sub.4 is an aliphatic group, cycloalkyl, optionally substituted aryl, or a heterocyclic group; andR.sub.
    Type: Grant
    Filed: June 10, 1991
    Date of Patent: October 20, 1992
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Jorge Casals-Stenzel, Gerda Mannesmann, Michael H. Town
  • Patent number: 5131945
    Abstract: Compounds of formula I ##STR1## are useful as herbicides, effective against dicotyledonous weeds.
    Type: Grant
    Filed: July 13, 1990
    Date of Patent: July 21, 1992
    Assignee: Shell Research Limited
    Inventors: Hans-Joachim Bissinger, Ludwig Schoeder, Helmut Baltruschat, Manfred Garrecht, Erich Raddatz, Wolfgang Fruhstorfer
  • Patent number: 5117037
    Abstract: A cis-bicyclo[4.3.0]non-2-ene derivative of the formula: ##STR1## wherein R is a hydrogen atom, or a protecting group for a hydroxyl group, R.sup.1 is a hydrogen atom, A C.sub.1 -C.sub.12 straight or branched chain alkyl group, a substituted or unsubstituted phenyl group, a C.sub.6 -C.sub.12 aralkyl group containing a condensed aromatic ring or an aromatic hetero ring, or 1 equivalent of a cation, A is --CH.dbd.CH--CH.sub.2 --, or --CH.sub.2 --CH.sub.2 --O--, R.sup.2 is a C.sub.3 -C.sub.10 straight or branched chain alkyl group, a C.sub.1 -C.sub.3 alkyl group substituted by an aryloxy group which may be substituted, a C.sub.3 -C.sub.12 straight or branched chain alkenyl group, a C.sub.3 -C.sub.8 straight or branched chain alkynyl group, a C.sub.1 -C.sub.3 alkyl group substituted by a phenyl or phenoxy group which may be substituted, by a C.sub.1 -C.sub.6 alkoxy group or by a C.sub.5 -C.sub.8 cycloalkyl group, R.sup.3 is a hydrogen atom, a methyl group, or a vinyl group, and X is a halogen atom.
    Type: Grant
    Filed: December 5, 1990
    Date of Patent: May 26, 1992
    Assignee: Sagami Chemical Research Center Toa Eiyo Ltd.
    Inventors: Masakatsu Shibasaki, Takahashi Atsuo, Tuyoshi Aoki, Hiroyasu Sato, Shin-ichi Yamada, Michiko Kudo, Takaji Yamaguchi, Kentaro Kogi, Sen-ichi Narita
  • Patent number: 5107014
    Abstract: The present invention relates to a new prostagrandine I analogous compounds represented by the following formula (I) and (II). ##STR1## wherein R.sub.1 is a hydrogen atom or alkyl group, at least one of R.sub.2 and/or R.sub.2 ' are a halogen atom, an alkyl group, a group containing an aromatic group, a hydroxyl group or an alkoxy group providing that the R.sub.2 and R.sub.2 ' are not simultaneously hydrogen atoms or salt thereof, which compound is expected as hypotensives.
    Type: Grant
    Filed: May 10, 1990
    Date of Patent: April 21, 1992
    Assignee: K.K. Ueno Seiyaku Oyo Kenkyujo
    Inventors: Ryuzo Ueno, Ryuji Ueno, Tomio Oda
  • Patent number: 5091431
    Abstract: Compounds having an optionally-substituted purine derivative portion and a carbobicyclic or heterobicyclic portion, which compounds are useful as phosphodiesterase inhibitors, are disclosed. Also disclosed are intermediates, methods for making the inhibitors, pharmaceutical compositions and methods for treating hypertension using the compounds.
    Type: Grant
    Filed: July 18, 1990
    Date of Patent: February 25, 1992
    Assignee: Schering Corporation
    Inventors: Deen Tulshian, Ronald J. Doll
  • 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: 5053526
    Abstract: Disclosed is a pharmaceutical having circulation ameliorating effect and antiulcer effect containing a prostaglandin I.sub.2 analogue represented by the formula shown below or a non-toxic salt of its salt or a cyclodextrin inclusion compound thereof as the effective ingredient: ##STR1## wherein R.sup.1 represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 4 to 7 carbon atoms or a phenyl group; A represents a pentyl group, a cyclopentyl group, a cyclohexyl group, a 1-methyl-3-hexynyl group, a 2-methyl-3-hexynyl group, a 1-methylhexyl group, a 2-phenethyl group, a 1,1-dimethylpentyl group, a 2-methylpentyl group, a 1-cyclohexylethyl group, a 2-methylhexyl group, a 1-methyl-3-pentynyl group or 1 2,6-dimethyl-5-heptenyl group; the double bond between the carbon atoms at 4- and 5-positions is E or Z or a mixture thereof, the asymmetric center in the substituent represented by A is R-configuration or S-configuration or a mixture thereof.
    Type: Grant
    Filed: April 16, 1990
    Date of Patent: October 1, 1991
    Assignees: Mitsubishi Kasei Corporation, Sagami Chemical Research Center
    Inventors: Masakatsu Shibasaki, Mikiko Sodeoka, Yuji Ogawa, Toshiaki Mase, Akira Ishibashi, Daijiro Horii, Toshiji Kanayama, Katsuhiko Iseki, Masaki Shinoda, Chiyoko Ishiyama, Yoshio Hayashi
  • Patent number: 5030654
    Abstract: A series of novel spiro-substituted glutaramide derivatives have been prepared, including the pharmaceutically acceptable salts thereof and bioprecursors therefor, wherein the spiro-substituent completes a 5- or 6-membered carbocycyclic ring and is located at the carbon atom adjacent to the carbamoyl group. These particular compounds are inhibitors of the neutral endopeptidase E.C.3.4.24.11 enzyme and are therefore useful in therapy as diuretic agents for the treatment of hypertension, heart failure, renal insufficiency and other disorders. Methods for preparing these compounds from known starting materials are provided.
    Type: Grant
    Filed: May 19, 1989
    Date of Patent: July 9, 1991
    Assignee: Pfizer Inc.
    Inventors: Ian T. Barnish, John C. Danilewicz, Keith James, Gillian M. R. Samuels, Nicholas K. Terrett, Michael T. Williams, Martin J. Wythes
  • Patent number: 5028733
    Abstract: Bicyclooctane and bicycloheptane prostaglandin intermediates have been synthesized.
    Type: Grant
    Filed: December 12, 1989
    Date of Patent: July 2, 1991
    Assignee: National Research Development Corporation
    Inventors: Robert L. Jones, Norman H. Wilson
  • Patent number: 5013758
    Abstract: (5E)-13,14,18,18,19,19-hexadehydro-3-oxa-6a-carbaprostaglandin I.sub.2 derivatives of Formula I ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 are hydrogen or alkyl of 1-5 carbon atoms, andR.sub.5 is an alkyl group of 1-5 carbon atoms, as well as the physiologically compatible salts thereof;have pharmacologically valuable activity.
    Type: Grant
    Filed: November 13, 1989
    Date of Patent: May 7, 1991
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Claus-Steffen Stuerzebecher, Martin Haberey, Ekkehard Schillinger, Michael H. Town
  • 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