Five-membered Carbocyclic Ring Having The Hetero Ring As Part Of One Substituent And -coo- As Part Of Another Substituent (e.g., Prostaglandin Intermediates, Etc.) Patents (Class 549/422)
  • Patent number: 11110053
    Abstract: Compositions comprising electro-activated aqueous solutions and methods for the prevention and treatment of dysfunctional cardiovascular conditions are provided.
    Type: Grant
    Filed: August 31, 2017
    Date of Patent: September 7, 2021
    Assignee: REVEN PHARMACEUTICALS INC.
    Inventors: Henk Van Wyk, Mariette Van Wyk, Trace Krebs, Peter Lange, Brian Denomme, Michael A. Volk
  • Patent number: 10849848
    Abstract: Compositions comprising electro-activated aqueous solutions and methods for the prevention and treatment of dysfunctional cardiovascular conditions are provided.
    Type: Grant
    Filed: August 31, 2017
    Date of Patent: December 1, 2020
    Assignee: REVEN PHARMACEUTICALS INC.
    Inventors: Henk Van Wyk, Mariette Van Wyk, Trace Krebs, Peter Lange, Brian Denomme, Michael A. Volk
  • Patent number: 8697751
    Abstract: An object of the present invention is to provide a stable aqueous pharmaceutical composition which suppresses degradation of prostaglandin F2? in a preparation containing prostaglandin F2?. The object was attained by formulating a prostaglandin F2? derivative into an oil-in-water emulsion together with an oil, for example, medium chain fatty acid triglyceride, a water-soluble polymer and water.
    Type: Grant
    Filed: August 10, 2011
    Date of Patent: April 15, 2014
    Assignee: Senju Pharmaceutical Co., Ltd.
    Inventors: Yusuke Sakai, Akira Ohtori
  • Publication number: 20120258402
    Abstract: A photoresist composition includes a polymer that includes a structural unit shown by the following formula (1), and a photoacid generator. R1 in the formula (1) represents a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group, Z represents a group that forms a divalent alicyclic group having 3 to 20 carbon atoms together with a carbon atom bonded to X, X represents an alkanediyl group having 1 to 6 carbon atoms, Y represents a hydrogen atom or —CR2R3(OR4), and R2 to R4 independently represent a hydrogen atom or a monovalent hydrocarbon group, provided that R3 and R4 optionally bond to each other to form a cyclic ether structure together with a carbon atom bonded to R3 and an oxygen atom bonded to R4.
    Type: Application
    Filed: April 4, 2012
    Publication date: October 11, 2012
    Applicant: JSR Corporation
    Inventors: Mitsuo SATO, Masafumi Yoshida
  • Patent number: 7132453
    Abstract: The present invention discloses methods and a kit for treating a respiratory syncytial virus infection. The method comprises providing an infection modulator, and administering a therapeutically effective amount of the infection modulator, wherein the respiratory syncytial virus infection is suppressed or precluded. The kit for suppressing a respiratory syncytial virus infection comprises an infection modulator, an applicator, and a set of instructions.
    Type: Grant
    Filed: March 14, 2003
    Date of Patent: November 7, 2006
    Assignee: Vanderbilt University
    Inventors: Ray Stokes Peebles, Jr., Koichi Hashimoto, Barney S. Graham
  • Patent number: 6713268
    Abstract: Methods to identify agents having ocular hypotensive activity which have reduced or absent ability to stimulate iridial hyperpigmentation are disclosed. The methods reside in part in detecting the ability of a test compound to interact with the FP receptor.
    Type: Grant
    Filed: June 26, 2001
    Date of Patent: March 30, 2004
    Assignee: Allergan, Inc.
    Inventors: David F. Woodward, Licheng Shi, Achim H-P Krauss, Clayton S. Spada, Sheila Mac Neil, Linda C. Smith-Thomas
  • Patent number: 6083501
    Abstract: A drug for prevention and therapy of diseases caused by fibrinoid formation or thrombus formation, as well as a model animal of fibrinoid formation or thrombus formation in the lung is disclosed. The drug for preventing and treating diseases caused by fibrinoid formation or thrombus formation in the lung according to the present invention comprises an inhibitor of interleukin 6 as an effective ingredient. The model animal of the diseases caused by fibrinoid formation or thrombus formation in the lung is a rat in which fibrinoid formation or thrombus formation actually occurs by induction with interleukin 6.
    Type: Grant
    Filed: March 14, 1996
    Date of Patent: July 4, 2000
    Assignee: Toray Industries, Inc.
    Inventors: Masayuki Miyata, Reiji Kasukawa, Masanobu Naruto, Nobutaka Ida, Yu-ichiro Sato, Katsuaki Kojima, Nobuo Ida
  • Patent number: 5990346
    Abstract: A prostaglandin having formula (I), (II), or (III): ##STR1## a process of production thereof, and inhibitors of cell migration caused by chemokines containing (I) or (II) as an active ingredient.
    Type: Grant
    Filed: February 26, 1997
    Date of Patent: November 23, 1999
    Assignee: Teijin Limited
    Inventors: Kenichiro Kataoka, Toru Minoshima, Tatsuki Shiota, Takaharu Tsutsumi, Takahiko Hada, Hiroko Tanaka, Takuya Morita, Noriaki Endo
  • Patent number: 5618959
    Abstract: A process for synthesizing prostaglandin E.sub.1, E.sub.2 and derivatives thereof is provided. The process is a "one-pot" method in which 2-furyllithium, copper cyanide, a lower alkyllithium reagent and either an (E)-alkenylstannane or a halogenide are combined with cyclopentenone (II) ##STR1## in which A, R.sup.6 and R.sup.7 are as defined herein. The reaction gives rise to the desired prostaglandin product in yields of 80% or higher.
    Type: Grant
    Filed: March 10, 1995
    Date of Patent: April 8, 1997
    Assignee: Vivus Incorporated
    Inventors: Miroslav Trampota, Bohumil Zak
  • Patent number: 5380900
    Abstract: Disclosed herein is an .alpha.-methylene-cyclopentanone derivative represented by the formula [I] below which is useful as an intermediate for pharmaceuticals and insecticides, especially prostaglandins. Also disclosed herein is a process for producing the derivative advantageously on an industrial scale. ##STR1## where X denotes (.alpha.-OZ, .beta.-H) or (.alpha.-H, .beta.-OZ), with Z representing a protecting group for the hydroxyl group; U denotes (.alpha.-H, .beta.-R.sup.1) or (.beta.-R.sup.1, .alpha.-H); R.sup.1 denotes ##STR2## where R.sup.2 denotes a protected hydroxyl group, a substituted or unsubstituted C.sub.1-15 alkyl group, a substituted or unsubstituted C.sub.2-15 alkenyl group, a substituted or unsubstituted C.sub.2-15 alkynyl group, or a substituted or unsubstituted C.sub.6-15 aryl group; Z' denotes a protecting group for the hydroxyl group; and k is 0 or 1).
    Type: Grant
    Filed: February 12, 1992
    Date of Patent: January 10, 1995
    Assignee: Nissan Chemical Industries, Limited
    Inventors: Fumie Sato, Kazutaka Arai, Katsuaki Miyaji
  • Patent number: 5254708
    Abstract: The present invention relates to substituted cyclopentanone and cyclohexanone derivatives and substituted cyclopentenone and cyclohexenone derivatives, which are useful as intermediates for pharmaceutical products and agricultural chemicals and especially useful for the synthesis of prostaglandins, and also to a process for producing the same.
    Type: Grant
    Filed: December 14, 1990
    Date of Patent: October 19, 1993
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Fumie Sato, Kazutaka Arai, Katsuaki Miyaji
  • Patent number: 5235072
    Abstract: The invention relates to 2-oxabicyclo[2.2.1]heptane derivatives of formula I ##STR1## as well as their enantiomers, in which, e.g., A means --(CH.sub.2).sub.n --, (E)-- or (Z)--CH.dbd.CH--, --C.tbd.C, --O-- or --S--,B means hydrogen, C.sub.1 -C.sub.10 alkyl, --OR.sup.2, halogen, --C.tbd.N, --N.sub.3, --COOR.sup.3,R.sup.1 means oxygen or a --CH.sub.2 group, ##STR2## Z means --(CH.sub.2).sub.p --, (E)--CH.dbd.CH--, --C.tbd.C--, W means a direct bond, a free or functionally modified hydroxymethylene group or a free or functionally modified ##STR3## in which the OH group can be respectively in alpha- or beta-position, D means a direct bond, a saturated alkylene group with 1-5 C atoms, a branched saturated or a straight-chain of branched unsaturated alkylene group with 2-5 C atoms,E means a direct bond, --C.tbd.C-- or --CH.dbd.CR.sup.7,R.sup.8 means hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.10 cycloalkyl, optionally substituted C.sub.6 -C.sub.12 aryl or a 5- or 6-member heterocyclic radical, andif R.sup.
    Type: Grant
    Filed: May 7, 1991
    Date of Patent: August 10, 1993
    Assignee: Schering Aktiengsellschaft
    Inventors: Ulrich Klar, Helmut Vorbruggen, Hartmut Rehwinkel, Karl H. Thierauch, Claus S. Sturzebecher
  • Patent number: 5231208
    Abstract: The present invention relates to substituted cyclopentanone and cyclohexanone derivatives and substituted cyclopentenone and cyclohexenone derivatives, which are useful as intermediates for pharmaceutical products and agricultural chemicals and especially useful for the synthesis of prostaglandins, and also to a process for producing the same.
    Type: Grant
    Filed: December 14, 1990
    Date of Patent: July 27, 1993
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Fumie Sato, Kazutaka Arai, Katsuaki Miyaji
  • Patent number: 5216183
    Abstract: A 2,3-epoxycyclopentanone represented by the formula (IV): ##STR1## wherein the variables are as defined in the specification, which is used in the preparation of a 2-substituted-2-cyclopentanone compound suitable for use as an anticancer agent and a bone formation accelerator.
    Type: Grant
    Filed: February 18, 1992
    Date of Patent: June 1, 1993
    Assignee: Teijin Limited
    Inventors: Satoshi Sugiura, Toru Minoshima, Atsuo Hazato, Yoshinori Kato
  • Patent number: 5116869
    Abstract: 2-Substituted-2-cyclopentenones represented by the formula (I): ##STR1## wherein A is a hydroxyl group or ##STR2## and B is a hydrogen atom or A and B are bonded together to form one bonding arm;R.sup.1 represents a substituted or unsubstituted hydrocarbon group having 1 to 10 carbon atoms;R.sup.2 represents a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms;R.sup.3 represents a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms; wherein,when R.sup.3 is a single bond bonded to the cyclopentene skeleton, X represents a hydrogen atom, a hydroxyl group or a protected hydroxyl group; andwhen R.sup.3 is a double bond bonded to the pentene skeleton, X represents a bonding arm constituting a part of said double bond; andm and n independently represent 0, 1 or 2.
    Type: Grant
    Filed: September 3, 1991
    Date of Patent: May 26, 1992
    Assignee: Teijin Limited
    Inventors: Satoshi Sugiura, Atsuo Hazato, Toru Minoshima, Yoshinori Kato, Yasuko Koshihara, Seizi Kurozumi
  • Patent number: 4837342
    Abstract: A prostacyclin analogue having the formula: ##STR1## wherein R.sup.1 is --CO.sub.2 R.sup.5 (wherein R.sup.5 is a hydrogen atom, a straight chain or branched alkyl group having from 1 to 12 carbon atoms, an aralkyl group having from 7 to 12 carbon atoms, a cycloalkyl group having from 4 to 7 carbon atoms and unsubstituted or substituted by at least one alkyl group having from 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, or one equivalent of a cation), or --CONR.sup.6 R.sup.7 (wherein each of R.sup.6 and R.sup.7 is a hydrogen atom or an alkyl group having from 1 to 10 carbon atoms, or R.sup.6 and R.sup.7 together with the adjacent nitrogen atom, form a 5- or 6-membered substituted or unsubstituted hetero ring which may contain a hetero atom other than said nitrogen atom); A is --CH.sub.2 CH.sub.2 CH.sub.2 --, CH.sub.2 --O--CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --O--CH.sub.2 -- or --CH.dbd.CHCH.sub.2 CH.sub. 2 --; B is trans --CH.dbd.CH-- or --C.
    Type: Grant
    Filed: February 13, 1987
    Date of Patent: June 6, 1989
    Assignees: Sagami Chemical Research Center, Toa Eiyo Ltd.
    Inventors: Masakatsu Shibasaki, Atsuo Takahashi, Tuyoshi Aoki, Kentaro Kogi, Yozo Nishimiya, Takeshi Nara, Takashi Yamaguchi
  • Patent number: 4822909
    Abstract: 7-Fluoroprostaglandins represented by the following formula (I): ##STR1## In the formula (I), R.sup.1 is a hydrogen atom or an alkyl group having from 1 to 10 carbon atoms, R.sup.2, R.sup.3 and R.sup.4 are hydrogen atoms or the same or different protective groups, respectively, and R.sup.5 is a straight chained, branched or cyclic alkyl group having from 3 to 7 carbon atoms.
    Type: Grant
    Filed: June 9, 1987
    Date of Patent: April 18, 1989
    Assignee: Asashi Glass Company Ltd.
    Inventors: Yasuda Arata, Kato Masao, Yamabe Masaaki, Uchida Keiichi
  • Patent number: 4804787
    Abstract: This invention relates to a process for making an enantiomer or racemic mixture of a compound of the formula ##STR1## wherein R is hydrogen, lower alkyl or a pharmaceutically acceptable, non-toxic salt of a compound wherein R is hydrogen; X is hydrogen, halo, trifluoromethyl, lower alkyl or lower alkoxy, and the wavy lines represent the .alpha. or .beta. configuration with the proviso that when one wavy line is .alpha. the other is .beta.; novel intermediates useful for preparing these compounds; and processes for making the intermediates.
    Type: Grant
    Filed: October 9, 1985
    Date of Patent: February 14, 1989
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Gary F. Cooper, Douglas L. Wren, Albert R. Van Horn, Tsung-Tee Li, Colin C. Beard
  • Patent number: 4797506
    Abstract: 6-substituted prostaglandins E.sub.1 which are compounds represented by the following formula [I] or their enantiomers or mixtures whereof in any ratio: ##STR1## wherein R.sup.1 represents a hydrogen atom, a C.sub.1 -C.sub.16 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted phenyl 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.3 -C.sub.8 alkynyl group, a phenyl group which may be substituted, a phenoxy group which may be substituted, a C.sub.3 -C.sub.
    Type: Grant
    Filed: October 18, 1985
    Date of Patent: January 10, 1989
    Assignee: Teijin Limited
    Inventors: Toshio Tanaka, Atsuo Hazato, Seizi Kurozumi
  • Patent number: 4780551
    Abstract: The invention relates to novel 3-phenyl-4-cyanopyrrole derivatives of the general formula ##STR1## wherein X has the following meanings: A: hydrogen or CO--R.sub.1, wherein R.sub.1 is C.sub.1 -C.sub.6 alkyl which is unsubstituted or substituted by halogen or C.sub.1 -C.sub.3 alkoxy; or is C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 alkynyl, or C.sub.1 -C.sub.6 alkoxy which is unsubstituted or substituted by halogen or C.sub.1 -C.sub.3 alkoxy; or is C.sub.3 -C.sub.6 alkenyloxy, C.sub.3 -C.sub.6 cycloalkyl or tetrahydrofur-2-yl;B: S--R.sub.2, wherein R.sub.2 is C.sub.1 -C.sub.3 haloalkyl;C: CH(Y)R.sub.3, wherein R.sub.3 is hydrogen or C.sub.1 -C.sub.8 haloalkyl and Y is hydroxy, halogen or OC(O)R.sub.4, wherein R.sub.4 is C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 -haloalkyl, C.sub.2 -C.sub.6 alkenyl, tetrahydrofur-2-yl, tetrahydropyran-2-yl or C.sub.1 -C.sub.6 alkoxycarbonyl;D: CH.sub.2 --Z, wherein Z is one of the groups ##STR2## in which formula each of R.sub.5 and R.sub.
    Type: Grant
    Filed: July 31, 1987
    Date of Patent: October 25, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Robert Nyfeler, Josef Ehrenfreund
  • Patent number: 4762935
    Abstract: This disclosure describes novel compounds which are useful as precursors in the synthesis of 9-oxo-11.alpha.,16-dihydroxy-16-vinyl-5-cis-13-trans-prostadienoate esters which possess activity as hypotensive agents and/or as vasodilators.
    Type: Grant
    Filed: October 6, 1986
    Date of Patent: August 9, 1988
    Assignee: American Cyanamid Company
    Inventors: Allan Wissner, Kenneth E. Green, Philip R. Hamann, Jeremy Levin
  • Patent number: 4736058
    Abstract: A novel prostacyclins expressed by the following formula (1) ##STR1## wherein a symbol between the 2-position and 3-position indicates single bond or double bond; G indicates --CO.sub.2 R.sup.5 or --CONR.sup.6 R.sup.7 in which R.sup.5 is a hydrogen atom, C.sub.1 -C.sub.10 alkyl group, substituted or unsubstituted alicyclic group, substituted or unsubstituted phenyl (C.sub.1 -C.sub.2) alkyl group, tri (C.sub.1 -C.sub.7) hydrocarbon-silyl group, or one equivalent cation, R.sup.6 and R.sup.7 are identical or different and each representing a hydrogen atom, or C.sub.1 -C.sub.10 alkyl group, or R.sup.6 and R.sup.7 are substituted or unsubstituted five to six-membered ring which may join together with a nitrogen atom to which they are linked and further contain a hetero atom; R.sup.1 indicates a hydrogen atom, or methyl group; R.sup.2 indicates an unsubstituted C.sub.3 -C.sub.8 alkyl group substituted or unsubstituted alicyclic group, or substituted C.sub.1 -C.sub.
    Type: Grant
    Filed: September 27, 1984
    Date of Patent: April 5, 1988
    Assignee: Teijin Limited
    Inventors: Shiro Ikegami, Seizi Kurozumi
  • Patent number: 4699989
    Abstract: 7-Fluoroprostaglandins represented by the following formula (I): ##STR1## In the formula (I), R.sup.1 is a hydrogen atom or an alkyl group having from 1 to 10 carbon atoms, R.sup.2, R.sup.3 and R.sup.4 are hydrogen atoms or the same or different protective groups, respectively, and R.sup.5 is a straight chained, branched or cyclic alkyl group having from 3 to 7 carbon atoms.
    Type: Grant
    Filed: February 11, 1985
    Date of Patent: October 13, 1987
    Assignee: Asahi Glass Company Ltd.
    Inventors: Yasuda Arata, Kato Masao, Yamabe Masaaki, Uchida Keiichi
  • Patent number: 4649156
    Abstract: The present invention provides a novel 6-nitroprostaglandin derivatives of the formula (I) ##STR1## wherein A, n, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are as defined in claim 1.The 6-nitroprostaglandin derivatives is useful as medicines because of its excellent pharmacological activities including platelet aggregation inhibiting activity, blood pressure lowering activity and anti-ulcerous activity, and useful as intermediate for other pharmaceutically active compounds such as 6-oxoprostaglandin derivatives, prostaglandin E.sub.1 derivatives, etc.
    Type: Grant
    Filed: July 19, 1985
    Date of Patent: March 10, 1987
    Assignee: Teijin Limited
    Inventors: Toshio Tanaka, Atsuo Hazato, Seizi Kurozumi
  • Patent number: 4600785
    Abstract: This invention relates to a process for making an enantiomer or racemic mixture of a compound of the formula ##STR1## wherein R is hydrogen, lower alkyl or a pharmaceutically acceptable, non-toxic salt of a compound wherein R is hydrogen; X is hydrogen, halo, trifluoromethyl, lower alkyl or lower alkoxy, and the wavy lines represent the .alpha. or .beta. configuration with the proviso that when one wavy line is a .alpha. the other is .beta.; novel intermediates useful for preparing these compounds; and processes for making the intermediates.
    Type: Grant
    Filed: December 22, 1983
    Date of Patent: July 15, 1986
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Gary F. Cooper, Douglas L. Wren, Albert R. Van Horn, Tsung-Tee Li, Colin C. Beard
  • Patent number: 4588823
    Abstract: Novel compounds of the following general formula: ##STR1##
    Type: Grant
    Filed: September 27, 1984
    Date of Patent: May 13, 1986
    Assignee: The Upjohn Company
    Inventor: Paul A. Aristoff
  • Patent number: 4585886
    Abstract: Novel compounds of the following general formula: ##STR1##
    Type: Grant
    Filed: September 27, 1984
    Date of Patent: April 29, 1986
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • 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: 4518790
    Abstract: This disclosure describes novel 15-deoxy-16-hydroxy-16- substituted prostanoic acids and congeners thereof having utility as bronchodilators as hypotensive agents, and as agents for the control of excessive gastric secretion, and particularly, alkyl esters, such as the methyl ester, of such acids.
    Type: Grant
    Filed: July 18, 1980
    Date of Patent: May 21, 1985
    Assignee: American Cyanamid Company
    Inventors: Middleton B. Floyd, Jr., Martin J. Weiss, Charles V. Grudzinskas, Sow-Mei L. Chen
  • 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
  • Patent number: 4444788
    Abstract: Compounds of the formula ##STR1## wherein the 9-chlorine atom can be in the .alpha.- or .beta.-position,R.sub.1 is OR.sub.2, or NHR.sub.3 wherein R.sub.3 is H or the acyl group ofa C.sub.1-15 hydrocarbon carboxylic or sulfonic acid;A is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH--,B is --CH.sub.2 --CH.sub.2 --,trans--CH.dbd.CH--, or --C.tbd.C--, ##STR2## wherein the OH-group in each case can be in the .alpha.- or .beta.-position, and can be etherified or esterified by tetrahydropyranyl, tetrahydrofuranyl, .alpha.-ethoxyethyl, trimethylsilyl dimethyl, tert-butylsilyl, tribenzylsilyl, acetyl, propionyl, butyryl or benzoyl;D and E together represent a direct bond orD is a straight-chain or branched alkylene group of 1-10 carbon atoms, optionally substituted by fluorine, andE is oxygen or sulfur or a direct bond, andR.sub.4 is hydroxy or hydroxy etherified or esterified as defined for W above;R.sub.5 is a C.sub.1-10 hydrocarbon aliphatic group; a C.sub.
    Type: Grant
    Filed: June 10, 1982
    Date of Patent: April 24, 1984
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Ekkehard Schillinger
  • Patent number: 4410720
    Abstract: 11-Unsubstituted 16-fluoro-prostaglandin E.sub.2 useful as blood pressure lowering agents.
    Type: Grant
    Filed: October 26, 1981
    Date of Patent: October 18, 1983
    Assignee: Hoffmann-La Roche Inc.
    Inventors: George W. Holland, Jane L. Jernow, Perry Rosen
  • Patent number: 4367340
    Abstract: Compounds of the general formula I are disclosed as useful intermediates in the preparation of prostanoids: ##STR1## wherein A represents O or H, OR.sub.z ;R.sup.z represents hydrogen or a protecting group;R.sup.x represents hydrogen or a protecting group; andR.sup.y represents halogen, a substituted thio group, di-substituted amino group, or a group of the formula R.sup.2, and R.sup.2 represents a straight-or branched-chain alkyl alkenyl or alkynyl group which may optionally be substituted by one or more carboxyl, carboxylic acid ester, or free or protected hydroxyl, thiol, aldehyde or keto groups;with the provisos that R.sup.x is not hydrogen when A is O and R.sup.y is R.sup.2 ; and that when A is H, OR.sup.z R.sup.y is R.sup.2 and R.sup.x and R.sup.z are not both hydrogen.Processes for the preparation of these compounds and of 2-substituted 4-hydroxy-cyclopent-2-en-1-one derivatives are also disclosed.
    Type: Grant
    Filed: March 4, 1981
    Date of Patent: January 4, 1983
    Assignee: The Australian National University
    Inventors: Rodney W. Rickards, Melvyn Gill, Robert M. Christie
  • Patent number: RE35230
    Abstract: A method of enantiomerically enriching chiral cyanohydrins is disclosed that involves selective cleavage of the unwanted enantiomer into its cleavage products HCN and the corresponding aldehyde or ketone by use of an enantioselective dehydrocyanation catalyst, coupled with simultaneous removal of at least one of the dehydrocyanation products.
    Type: Grant
    Filed: February 7, 1994
    Date of Patent: May 7, 1996
    Assignee: Bend Research, Inc.
    Inventor: Paul van Eikeren