Two Rings Only In Acid Moiety Patents (Class 560/118)
  • Patent number: 5359126
    Abstract: Preparing cyclohexanediones of the formula ##STR1## an aldehyde is reacted with a ketene to give a polymer having the repeating unit ##STR2## wherein n ranges from about 2 to about 1,000. The polymer is hydrolyzed to produce a mixture of an unsaturated acid of the formula R--CH.dbd.C(R.sub.1)--COOH and a hydroxy ester or acid of the formula R--CH(OH)C(R.sub.1)(R.sub.2)--COOR.sub.3, the mixture is then contacted with an esterifying agent to convert the acids to esters. The ester mixture is contacted with a dehydrating agent to convert the hydroxy ester to unsaturated ester of the formula R--CH.dbd.C(R.sub.1)--COOR.sub.3. The unsaturated ester is contacted with a basic catalyst to cyclize it to the cyclic dione ester of the formula ##STR3## and this ester is then hydrolyzed and decarboxylated to give the cyclohexanedione give the productwherein:R is selected, e.g.
    Type: Grant
    Filed: February 7, 1994
    Date of Patent: October 25, 1994
    Assignee: Eastman Chemical Company
    Inventor: Charles A. McCombs
  • Patent number: 5340835
    Abstract: A compound selected from the group consisting of all stereoisomeric forms and mixtures thereof of a compound of the formula ##STR1## wherein Y and Z are individually selected from the groups consisting of hydrogen, halogen, --CF.sub.3, alkyl, alkoxy and alkylthio of 1 to 8 carbon atoms and aryl, aryloxy and arylthio of up to 14 carbon atoms optionally substituted with at least one member of the group consisting of halogen, hydroxy optionally esterified etherified, --CF.sub.3 and alkyl of 1 to 8 carbon atoms and R is alkyl of 1 to 8 carbon atoms or the remainder of a pyrethrinoid alcohol having excellent pesticidal properties and their preparation and intermediates.
    Type: Grant
    Filed: January 19, 1993
    Date of Patent: August 23, 1994
    Assignee: Roussel-UCLAF
    Inventors: Didier Babin, Marc Benoit, Jean-Pierre Demoute, Fabienne Pilorge, Nicole Reinier
  • Patent number: 5338879
    Abstract: A composition comprising a lactone-modified alicyclic compound (I), or an epoxidized lactone-modified alicyclic compound (II) of the following formulae: ##STR1## wherein R is an alkyl group, an aromatic group or an alkenyl group having carbon number of from 1 to 30, Y.sup.1 is at least one of the structural groups; ##STR2## Y.sup.2 is at least one of the structural group; ##STR3## X is the structural group; ##STR4## and R.sup.a and R.sup.b each independently is hydrogen or a methyl group, c and c' represent a number of from 4 to 8, from n1 to nL represents 0 or a number of more than 0, respectively, and n1+n2+n3+ . . . +nL corresponds to the total mole numbers of a lactone introduced into one molecule.These compositions can be made into a heat-curable composition, a photo-curable composition, a polymerizable composition and another photo-curable composition.
    Type: Grant
    Filed: August 13, 1992
    Date of Patent: August 16, 1994
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Takaaki Fujiwa, Shin Takemoto, Tomohisa Isobe, Yoshiyuki Harano
  • Patent number: 5264152
    Abstract: An optically active compound represented by the formula (I): ##STR1## wherein R is a straight or branched chain alkyl or alkoxy group having 1 to 15 carbon atoms, ##STR2## is a 1,4-cyclohexylene or 1,4-phenylene group, ##STR3## is a 1,4-phenylene or 3-fluoro-1,4-phenylene group, X is a mono-, di- or tri-fluoromethyl group, W is a straight or branched chain or cyclic alkylene group having 1 to 16 carbon atoms or a straight or branched chain alkenylene group having 2 to 16 carbon atoms, Y is a bond or --COO--, and Z is a straight or branched chain alkyl group having 1 to 8 carbon atoms, a phenyl group or a hydrogen atom, which is useful as a component of ferroelectric liquid crystal compositions or as a device utilizing said composition.
    Type: Grant
    Filed: April 7, 1992
    Date of Patent: November 23, 1993
    Assignee: Sharp Kabushiki Kaisha
    Inventors: Makoto Shiomi, Mitsuhiro Koden, Tomoaki Kuratate, Fumiaki Funada
  • Patent number: 5252707
    Abstract: There are disclosed a novel inositol-1,4,5-triphosphoric acid derivative, inositol-1,3,4-triphosphoric acid derivative, inositol-1,3,4,5-tetraphosphoric acid derivative, and a bonded substance of the same and a protein. They control the metabolic process of an organism concerned with calcium ions to thereby exert a medicinal virtue.
    Type: Grant
    Filed: May 15, 1991
    Date of Patent: October 12, 1993
    Assignee: Mitsui Toatsu Chemicals Incorporated
    Inventors: Shoichiro Ozaki, Yutaka Watanabe, Masato Hirata, Akira Awaya
  • Patent number: 5241104
    Abstract: Optically active mono-esters of dicarboxylic acid of the formula III: ##STR1## being useful as intermediates for preparing optically active natural products or medicines; asymmetric synthesis process for preparing thereof being characterized by the reaction of an acid anhydride with an (R)- or (S)-arylacetic acid derivative; and the key substances therefor are also claimed.
    Type: Grant
    Filed: June 23, 1992
    Date of Patent: August 31, 1993
    Assignee: Shionogi & Co., Ltd.
    Inventors: Mitsuaki Ohtani, Takaharu Matsuura
  • Patent number: 5238602
    Abstract: Compounds of the formula ##STR1## wherein n stands for the number 0 or 1; the rings A.sup.1, A.sup.2 and A.sup.3 represent 1,4-phenylene, 2-fluoro-1,4-phenylene or trans-1,4-cyclohexylene or one of these rings also represents a 2,5-disubstituted pyrimidine ring or a trans-2,5-disubstituted m-dioxane ring; X.sup.1 represents a single covalent bond, --COO--, --OOC--, --CH.sub.2 CH.sub.2 --, p--C.sub.6 H.sub.4 --, --CH.sub.2 CH.sub.2 --p-- C.sub.6 H.sub.4 --, --CH.sub.2 CH.sub.2 --p--C.sub.6 H.sub.4 --CH.sub.2 CH.sub.2 -- or, insofar as the rings A.sup.1 and A.sup.2 represent 1,4-phenylene, also --NON--; R.sup.2 represents 1E-alkenyl, 2Z-alkenyl, 3E-alkenyl, 4-alkenyl or alkenyloxy, with the proviso that the oxygen atom in alkenyloxy is linked with a saturated carbon atom; and R.sup.1 signifies 1E-alkenyl, 2Z-alkenyl, 3E-alkenyl, 4-alkenyl or, insofar as R.sup.2 represents alkenyloxy, also alkyl, their manufacture, as well as liquid crystalline mixtures and the use for electro-optical purposes.
    Type: Grant
    Filed: May 26, 1987
    Date of Patent: August 24, 1993
    Assignee: Hoffmann La Roche Inc.
    Inventors: Martin Petrzilka, Martin Schadt
  • Patent number: 5194669
    Abstract: Disclosed are processes for the preparation of alkyl (alkoxycarbonylcyclohexyl)cyclohexenecarboxylates by the dimerization of alkyl 3-cyclohexenecarboxylates and the dehydrogenation of the alkyl (alkoxycarbonylcyclohexyl) cyclohexenecarboxylates to dialkyl biphenyldicarboxylates. The processes are especially useful for the preparation of dialkyl 4,4'-biphenyldicarboxylates which are intermediates in the preparation of high performance polyesters.
    Type: Grant
    Filed: September 13, 1991
    Date of Patent: March 16, 1993
    Assignee: Eastman Kodak Company
    Inventors: J. Adrian Hawkins, Patricia N. Mercer, Michael Bellas
  • Patent number: 5187304
    Abstract: Provided are 1,5-bis(4-carboxycyclohexyl)-3-pentanol and its esters and processes for their preparation. Also provided are polyester compositions containing this residue, thermosetting coating compositions containing the polyesters, and coatings and casted or molded articles made therefrom.
    Type: Grant
    Filed: May 1, 1992
    Date of Patent: February 16, 1993
    Assignee: Eastman Kodak Company
    Inventors: William W. Blount, Jr., Joseph R. Zoeller
  • Patent number: 5177109
    Abstract: Compounds, compositions and methods are described for treating a CNS disorder such as a cognitive disorder, epilepsy, depression, Parkinson's disease, Alzheimer's disease, a neurodegenerative disease or neurotoxic injury. Compound of interest are 2-amino-4,5-methyleneadipic acid compounds and derivatives defined by the formula I: ##STR1## wherein R.sup.1 is selected from hydrido, alkyl, cycloalkyl, aralkyl, aryloxyalkyl, arylthioalkyl, ##STR2## with each of R.sup.2, R.sup.3, R.sup.4 and R.sup.5 being independently selected from hydrido, alkyl, cycloalkyl, aryl and aralkyl; wherein each of X and Y is independently selected from hydroxyl, alkoxy, alkylthio, amino and ##STR3## with each of R.sup.6 and R.sup.7 being independently selected from hydrido, alkyl, cycloalkyl, aryl and aralkyl; wherein any of R.sup.1 through R.sup.
    Type: Grant
    Filed: July 19, 1991
    Date of Patent: January 5, 1993
    Assignee: G. D. Searle & Co.
    Inventors: Roberto Pellicciari, Benedetto Natalini, Maura Marinozzi, Alexis A. Cordi, Joseph B. Monahan, Thomas H. Lanthorn
  • Patent number: 5177251
    Abstract: The present invention relates to a novel class of halogenated tetraenyl prostaglandin compounds represented by the following general formula ##STR1##or a pharmaceutically acceptable salt thereof, whereinY is --CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --;R.sub.1 is H or a lower alkyl of 1 to 6 carbons;n is an integer from 0 to 3;m is an integer from 0 to 3 and n+m=3; X is Cl or F provided that when X is Cl, n is 2 and m is 1;R.sub.2 and R.sub.3 are independently H, lower alkyl from 1 to 6 carbons, Cl, --CH.sub.2 Cl, --CH.sub.2 F, --CHCl.sub.2, --CCl.sub.3, or taken together form a cycloalkyl of 3 to 6 carbons;R.sub.4 is H, lower alkyl from 1 to 6 carbons, Cl, F or taken together with R.sub.3 form a cycloalkenyl of 4 to 6 carbons; and provided that at least one of --CH.sub.n X.sub.m, R.sub.2, R.sub.3 and R.sub.4 includes a chlorine or fluorine atom.
    Type: Grant
    Filed: December 24, 1991
    Date of Patent: January 5, 1993
    Assignee: G. D. Searle & Co.
    Inventors: Paul W. Collins, Steven W. Kramer, Robert L. Shone
  • Patent number: 5164526
    Abstract: Compounds of formula I ##STR1## wherein R.sub.1 and R.sub.2 are the same or different and each represent hydrogen, alkyl, alkenyl, cycloalkyl, aryl or aralkyl are produced by a new environmentally acceptable process.
    Type: Grant
    Filed: October 2, 1990
    Date of Patent: November 17, 1992
    Assignee: Biochemie Gesellschaft m.b.H.
    Inventor: Ingolf Macher
  • Patent number: 5164412
    Abstract: A Derivative of 5-hetero-6-oxo-PGE A derivative of 5-hetero-6-oxo-PGE of the formula: ##STR1## wherein R.sup.1 is (1) a group of the formula: COOR11(2) hydroxymethylcarbonyl,(3) hydroxymethyl or(4) a group of the formula:CO--AAwherein AA is an amino acid-residue,Z is oxygen, sulfur or a group of the formula: NR21 wherein R21 is hydrogen or alkyl of C1--4;R2 is a single-bond or alkylene of C1--4;R3 isi) alkyl of C1-7,ii) cycloalkyl of C4-7 or cycloalkyl of C4-7 substituted by alkyl of C1-7,iii) phenyl, phenoxy, phenyl or phenoxy substituted by one group selected from alkyl of C1-4, halogen and trihalomethyl, is single-bond or a double bond.Possess PG-like activity, especially cytoprotection, and therefore are useful for treatment for and/or prevention of cytodamage.
    Type: Grant
    Filed: April 8, 1991
    Date of Patent: November 17, 1992
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Yoshitaka Konishi, Masanori Kawamura
  • 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: 5154753
    Abstract: Cyclohexenone derivatives of the formula ##STR1## where R.sup.1, R.sup.2, R.sup.3, Y and Z have the meanings given in the disclosure, processes for their manufacture, herbicidal and growth-regulating agents containing the novel active ingredients, and processes for combating unwanted plant growth and for regulating plant growth.
    Type: Grant
    Filed: August 14, 1991
    Date of Patent: October 13, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Norbert Meyer, Johann Jung, Wilhelm Rademacher, Dieter Kolassa, Rainer Becker, Dieter Jahn, Michael Keil, Ulrich Schirmer, Bruno Wuerzer
  • Patent number: 5142099
    Abstract: An enantioselective process for the preparation of hemicaronic aldehyde with a cis or trans structure and novel intermediates.
    Type: Grant
    Filed: November 13, 1991
    Date of Patent: August 25, 1992
    Assignee: Roussel Uclaf
    Inventor: Alain Krief
  • 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: 5117042
    Abstract: A method of treatment for improving encephalic function which comprises administering, to a subject in need of such treatment, a 15-keto-prostaglandin compound in an amount effective for improvement of encephalic function.
    Type: Grant
    Filed: November 21, 1990
    Date of Patent: May 26, 1992
    Assignee: K.K. Ueno Seiyaku Oyo Kenkyujo
    Inventors: Ryuji Ueno, Hiroyoshi Osama, Tomio Oda
  • 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: 5095137
    Abstract: The amides of cyclomethylen-1,2-bicarboxylic acids having the formula: ##STR1## wherein A represents ##STR2## R.sup.1 represents --H, --CH.sub.3, --CH.sub.2 --CH.sub.3, --CH(CH.sub.3).sub.2, ##STR3## R.sup.2 represents --H, CH.sub.3, --CH.sub.2 --CH.sub.3, --CH(CH.sub.3).sub.2, --CH.sub.2 --CH.sub.2 --CH.sub.3, --CH.sub.2 --CH(CH.sub.3).sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.3, --CH.sub.2 --C.sub.6 H.sub.5, --C.sub.6 --H.sub.5 ;R.sup.3 represents --H, --CH.sub.3, --C.sub.2 H.sub.5, ##STR4## R.sup.5 represents --H, --CH.sub.3, --C.sub.2 H.sub.5, --CH.sub.2 C.sub.6 H.sub.5, ##STR5## Y=--H, --CH.sub.3, --CH(CH.sub.3).sub.2 Z=--H,--CH.sub.3, --C(CH.sub.3).sub.3, --CH(C.sub.2 H.sub.5).sub.2, ##STR6## R.sup.4 =R.sup.5, ##STR7## m is 0 or 1 and n is an integer varying between 0 and 3, are endowed with ACE-inhibiting activity and are thus therapeutically useful as anti-hypertension agents.
    Type: Grant
    Filed: October 9, 1990
    Date of Patent: March 10, 1992
    Assignee: Laboratori Guidotti SpA
    Inventors: Luigi Turbanti, Guido Cerbai, Marco Criscuoli
  • Patent number: 5089524
    Abstract: Tetraenyl Prostanoic Acid derivatives which are useful as prodrugs for the treatment of peptic ulcer disease and are represented by the following general formula ##STR1## are disclosed.
    Type: Grant
    Filed: June 28, 1990
    Date of Patent: February 18, 1992
    Assignee: G. D. Searle & Co.
    Inventors: Paul W. Collins, Alan F. Gasiecki
  • Patent number: 5081282
    Abstract: Bicyclo prostaglandin analogues have been prepared.
    Type: Grant
    Filed: January 13, 1988
    Date of Patent: January 14, 1992
    Assignee: National Research Development Corporation
    Inventors: Robert L. Jones, Norman H. Wilson
  • Patent number: 5077309
    Abstract: Novel compounds have the formula (I) ##STR1## where ##STR2## represents one of the divalent cyclic groups ##STR3## the letters a and b indicating in each case the points of attachment of the substituents R.sup.1 and CV(R.sup.2)-NV'R, respectively; R.sup.1 is a group --(CH.sub.2).sub.b --(A).sub.a --(CH.sub.2).sub.c --B--CH.sub.2 --CO.sub.2 R' in which A and B are each separately oxygen or sulphur, a is 0, b is 0 and c is an integer from 3 to 10, or a is 1, b is 0 or an integer from 1 to 7 and c is an integer from 2 to 9 with the sum of b and c being from 2 to 9, and CO.sub.2 R' is a carboxy group or an amide, ester or salt derivative thereof; V and V' either each separately is hydrogen or together are the second bond of a carbon-nitrogen double bond; R.sup.2 is hydrogen, an aliphatic hydrocarbon group or an aliphatic hydrocarbon group substituted by an aromatic group directly or through an oxygen or sulphur atom; and R is a group --OR.sup.3, --OR.sup.4, --D--R.sup.3, --N.dbd. R.sup.5 or --NW.G.
    Type: Grant
    Filed: March 28, 1990
    Date of Patent: December 31, 1991
    Assignee: National Research Development Corporation
    Inventors: Robert L. Jones, Norman H. Wilson
  • Patent number: 5051527
    Abstract: The invention lies in novel ferroelectric liquid crystal compounds particularly represented by the general formulae, having a good responsibility in relation to the applied electric field and a wide range of phase transition points inclusive of the room temperature so as to be useful alone as the liquid crystal material but also to be mixed with other liquid crystal compounds for expanding the phase transition points to a desired range and making the response speed of the liquid crystal composition faster. ##STR1## In the formulae, m and n are same or different with each other and represent an integral of 1-20.
    Type: Grant
    Filed: February 28, 1989
    Date of Patent: September 24, 1991
    Assignee: Showa Shell Sekiyu K.K.
    Inventors: Yoshiichi Suzuki, Takashi Hagiwara, Hiroyuki Mogamiya
  • Patent number: 5043451
    Abstract: There are provided compounds of the formula: ##STR1## wherein R.sub.1 is a hydrogen or C.sub.1 -C.sub.5 alkyl; R.sub.2 is an C.sub.1 -C.sub.10 alkyl, aryl, aralkyl, or pyridyl, where the aryl, aralkyl, or pyridyl are unsubstituted or are substituted by C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, nitro, hydroxy, carboxy, amino, C.sub.1 -C.sub.5 alkylamino, C.sub.1 -C.sub.5 dialkylamino whose two alkyl groups may be different from each other, C.sub.2 -C.sub.3 alkanoylamino, or halogen and X is an C.sub.1 -C.sub.7 alkylene, C.sub.2 -C.sub.7 alkenylene, --CH(F)CH.dbd.CH(CH.sub.2).sub.3 --, --(CH.sub.2).sub.3 --S--(CH.sub.2).sub.2 --, --CH.sub.2).sub.2 --S--(CH.sub.2).sub.3 --, --C.sub.6 H.sub.4 --O--CH.sub.2 --or --CH.sub.2 CH.dbd.CH--m--C.sub.6 H.sub.4 --, or their pharmaceutically acceptable salts. The compounds are useful as antithrombotic, anti-vasoconstricting and anti-bronchoconstricting drugs.
    Type: Grant
    Filed: April 27, 1990
    Date of Patent: August 27, 1991
    Assignee: Shionogi & Co., Ltd.
    Inventors: Mitsuaki Ohtani, Fumihiko Watanabe, Tadadiko Tsushima, Kenji Kawada, Susumu Kamata
  • Patent number: 5041613
    Abstract: Processes, intermediates, and products involved in preparing cyclohexanediones of the formula ##STR1## are disclosed. An aldehyde of the formula R--CHO is reacted with a ketone type compound of the formula (R.sub.1)(R.sub.2)C.dbd.C.dbd.O at a temperature below about 110.degree. C. to give a polymer having the repeating unit --OCH(R)C(R.sub.1)(R.sub.2)CO].sub.n wherein n ranges from about 2 to about 1,000. The polymer is hydrolyzed with alcoholic or aqueous base to produce a mixture of an unsaturated acid of the formula R--CH.dbd.C(R.sub.1)--COOH and a hydroxy ester or acid of the formula R--CH(OH)C(R.sub.1)(R.sub.2)--COOR.sub.3, the mixture is then contacted with an esterifying agent to convert the acids to esters. The ester mixture is contacted with a dehydrating agent to convert the hydroxy ester to unsaturated ester of the formula R--CH.dbd.C(R.sub.1)--COOR.sub.3.
    Type: Grant
    Filed: August 28, 1989
    Date of Patent: August 20, 1991
    Assignee: Eastman Kodak Company
    Inventor: Charles A. McCombs
  • 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: 5036098
    Abstract: Compounds of the formula (I): ##STR1## exhibit anti-cholingeric and calcium antagonistic action and are used for treating pollakiuria and incontinence in humans and animals.
    Type: Grant
    Filed: September 14, 1989
    Date of Patent: July 30, 1991
    Assignee: Nippon Shinyaku Co., Ltd.
    Inventors: Kiyoshi Kimura, Masahiro Kise, Iwao Morita
  • Patent number: 5011974
    Abstract: For the preparation of derivatives of 2-diethylamino-1-methylethyl cis-1-hydroxy-(bicyclohexyl)-2-carboxylate, particularly the citrate, maleate, fumarate and pamoate, the oily base is initially converted to the phosphate, whereby solid products are obtained, both soluble and insoluble in water.
    Type: Grant
    Filed: March 1, 1989
    Date of Patent: April 30, 1991
    Assignee: Laboratori Guidotti
    Inventor: Franco Sbarbaro
  • Patent number: 5004752
    Abstract: The invention relates to 9-halo-15-cycloalkyl prostaglandin derivatives of Formula I ##STR1## wherein R.sub.1 is hydrogen or methyl,R.sub.2 is fluorine or chlorine,n is 0 or 1,and, if R.sub.1 is hydrogen, the salts thereof with physiologically compatible bases or the cyclodextrin clathrates thereof, processes for their preparation, and their pharmaceutical usage.
    Type: Grant
    Filed: May 8, 1989
    Date of Patent: April 2, 1991
    Assignee: Schering Aktiengesellschaft
    Inventors: Bernd Raduechel, Werner Skuballa, Helmut Vorbrueggen, Olaf Loge, Ekkehard Schilliner
  • Patent number: 4992577
    Abstract: A process for preparing a compound of the formula ##STR1## in which Y is halogen, alkyl or cycloalkyl optionally substituted by halogen or C.sub.1-4 -alkoxy, alkenyl optionally substituted by halogen, aryl, heteroaryl or alkoxycarbonyl,X is hydrogen, halogen or optionally halogen-substituted alkyl, orX and Y, together with the adjacent C atom, form a saturated cycloalkphatic ring having up to 6 C atoms, andR is hydrogen or C.sub.1 -C.sub.4 -alkyl, comprising reacting an aldehyde of the formula ##STR2## with 2-methylbutan-3-one of the formula ##STR3## in the presence of a hydrohalic acid thereby to form a 4,4-dimethyl-3-halogeno-1-hexen-5-one of the formula ##STR4## in which Hal is halogen, halogenating said compound to produce a compound of the formula ##STR5## and reacting said compound with a base of the formulaR--OM (VI)in whichM is one equivalent of an alkali or alkaline earth metal ion.Compounds IV and V are new. By suitable conditions the trans isomer is selectively produced.
    Type: Grant
    Filed: May 22, 1989
    Date of Patent: February 12, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Lantzsch, Dieter Arlt, Manfred Jautelat
  • Patent number: 4975444
    Abstract: Compounds of the formula ##STR1## wherein A is a carbocyclic, saturated or unsaturated ring; R.sup.1 is hydrogen or alkyl; R and R.sup.4 are each alkyl, cycloalkyl, benzyl or a readily hydrolyzable ester group; Y is a bond or a straight or branch alkylene; R.sup.2 is hydrogen, aryl, heterocyclic, R.sup.6 CONR.sup.5, R.sup.7 NR.sup.5 CO, R.sup.7 NR.sup.5 SO.sub.2 --or R.sup.8 SO.sub.2 NR.sup.5 --where R.sup.5 is hydrogen, alkyl or aralkyl; R.sup.6 is alkyl, aryl, aralkyl, heterocyclic, heterocyclyalkyl or a group of the formula ##STR2## where R.sup.9 is hydrogen, hydroxy, alkoxy, alkyl, hydroxyalkyl, aralkyl, alkylene, heterocyclic, heterocyclylalkyl, R.sup.12 CONH--, R.sup.12 SO.sub.2 NH-- or (R.sup.13).sub.2 N--; R.sup.10 and R.sup.11 are each hydrogen or alkyl; or R.sup.10 is hydrogen and R.sup.11 is aminoalkyl, imidazolylmethyl, aryl, aralkyl, aralkoxyalkoxy, hydroxyalkyl or methylthioalkyl; or R.sup.10 and R.sup.
    Type: Grant
    Filed: August 25, 1989
    Date of Patent: December 4, 1990
    Assignee: Pfizer Inc.
    Inventors: John C. Danilewicz, Keith James, Ryszard J. Kobylecki
  • Patent number: 4968820
    Abstract: The new compounds produced from a molecular structural element with two chirality centers and at least one mesogenic structural element are defined by the general formula (I) ##STR1## in which the symbols have the following meaning: Y.sup.1, Y.sup.2, Y.sup.3, Y.sup.4 = in any two cases (a) hydroxy and MC--CO--O or, independently of each other, MC--CO--O and (b), independently of each other (C.sub.1 -C.sub.10)alkoxy, MC denoting the molecular radical of a mesogenic carboxylic acid after splitting off a COOH group, and it being possible for Y.sup.2 and Y.sup.3, in the case of (C.sub.1 -C.sub.10)alkoxy, also to be jointly part of a dioxolane ring, or Y.sup.1 and Y.sup.4 jointly = 0 as part of a tetrahydrofuran ring, and Y.sup.2 and Y.sup.3 = hydroxy and MC--CO--O or, independently of each other, MC--CO--O. Said esters preferably find application as dopants in twistable liquid crystal phases in which they produce temperature compensation and twisting.
    Type: Grant
    Filed: July 11, 1988
    Date of Patent: November 6, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunter Scherowsky, Manel Gunaratne
  • Patent number: 4966726
    Abstract: The new compounds produced from a molecular structural element with two chirality centers and at least one mesogenic structural element are defined by the general formula (I) ##STR1## in which the symbols have the following meaning: Y.sup.1 =H, (C.sub.1 -C.sub.10)alkyl, MC--CH.sub.2 or MC--CO, MC denoting the molecular radical of a mesogenic carboxylic acid after splitting off a COOH group,Y.sup.2 =(C.sub.1 -C.sub.10)alkyl, MC--CH.sub.2 or MC--CO, it being possible for Y.sup.1 and Y.sup.2 to jointly represent a MC--CH group, which is then part of a dioxolane ring,X=COOR.sup.1, CONH.sub.2, CONR.sup.2 R.sup.3 or C.tbd.N,R.sup.1 =(C.sub.1 -C.sub.10)alkyl or MC--CH.sub.2, andR.sup.2, R.sup.3 =H and (C.sub.1 -C.sub.4)alkyl or, independently of each other, (C.sub.1 -C.sub.4)alkyl.Said esters preferably find application as dopants in twistable liquid crystal phases in which they produce temperature compensation and twisting.
    Type: Grant
    Filed: July 18, 1988
    Date of Patent: October 30, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunter Scherowsky, Manel Gunaratne
  • Patent number: 4965279
    Abstract: Novel cyclopropyl aza prostaglandin analogs are disclosed having the formula ##STR1## wherein A can be carbonyl, sulfonyl or a single bond. These compounds are useful, for example, as thromboxane antagonists.
    Type: Grant
    Filed: November 18, 1988
    Date of Patent: October 23, 1990
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Raj N. Misra, David M. Floyd, Steven E. Hall
  • Patent number: 4960792
    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-dependant, neutral endopiptidase.
    Type: Grant
    Filed: May 8, 1989
    Date of Patent: October 2, 1990
    Assignee: Pfizer Inc.
    Inventors: John C. Danilewicz, Keith James
  • Patent number: 4957940
    Abstract: Certain bicyclo [2.2.1] heptane and bicyclo [2.2.2] octane substituted tetrahydro-2H-pyran-2-ones and the corresponding ring-opened acids derived therefrom are potent inhibitors of the enzyme 3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMG-CoA reductase) and are useful as hypocholesterolemic and hypolipidemic agents.
    Type: Grant
    Filed: November 21, 1989
    Date of Patent: September 18, 1990
    Assignee: Warner-Lambert Company
    Inventor: Bruce D. Roth
  • Patent number: 4945178
    Abstract: Acetoacetic esters of the formula R--OOCCH.sub.2 COCH.sub.3 are reacted with an unsaturated ester of the formula R.sup.1 R.sup.2 C.dbd.CHCOOR.sup.3 in the presence of basic catalyst such as ethanolic sodium ethoxide to give compound I of the formula ##STR1## and the alcohol by-product HOR.sup.3. By known hydrolysis and decarboxylation procedures, compound I is convertible to compound II of the formula ##STR2## In the above formulas, R is alkyl, R.sup.1 and R.sup.2 are each selected independently from H, alkyl, alkylthioalkyl, cycloalkyl, alkyl substituted cycloalkyl, aryl, substituted aryl, heterocyclic, or substituted heterocyclic, and R.sup.3 is alkyl or cycloalkyl. These compounds I and II are intermediates in the preparation of known herbicides.
    Type: Grant
    Filed: February 24, 1989
    Date of Patent: July 31, 1990
    Assignee: Eastman Kodak Company
    Inventor: Charles A. McCombs
  • Patent number: 4945106
    Abstract: Prostaglandin analogues exhibiting activity at thromboxane receptor sites have been prepared.
    Type: Grant
    Filed: July 6, 1989
    Date of Patent: July 31, 1990
    Assignee: National Research Development Corporation
    Inventors: Robert L. Jones, Norman H. Wilson
  • Patent number: 4943384
    Abstract: Cyclohexane derivatives of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --R.sup.2 IwhereinR.sup.1 and R.sup.2 are each H or an alkyl group which has 1-10 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or --CO-groups, and/or --CO--O-- groups and/or --CH.dbd.CH-- groups, or are F, Cl, Br, CN or R.sup.3 --A.sup.3 --Z.sup.2 --,A.sup.1 is --A--, A.sup.4 --Z.sup.o --A-- or --A--Z.sup.o --A.sup.4 --,A is a trans-1,4-cyclohexylene or 1,4-cyclohexenylene group which is unsubstituted or is monosubstituted or polysubstituted in the 2-, 3-, 5- and/or 6-position by F and/or Cl and/or Br and/or CN and/or an alkyl group or a fluorinated alkyl group each of which has 1-10 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or --CO-- groups and/or --CO--O-- groups, which trans-1,4-cyclohexylene or 1,4-cyclohexenylene group can optionally also be substituted in the 1-position and/or 4-position and one or two CH.sub.
    Type: Grant
    Filed: November 21, 1986
    Date of Patent: July 24, 1990
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Wolfgang Sucrow, Herbert Wolter, Rudolf Eidenschink
  • Patent number: 4935446
    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: March 30, 1989
    Date of Patent: June 19, 1990
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Katsuhiro Imaki, Hajimu Miyake, Tadao Okegawa
  • Patent number: 4929751
    Abstract: A vinyl tricarbonyl compound of the formula ##STR1## or its monohydrate of the formula ##STR2## wherein R.sub.1 is a hydrogen, halogen, unsubstituted or substituted C.sub.1 to C.sub.30 alkyl, unsubstituted or substituted aryl, arylalkyl, and cycloalkyl with 3 to 7 carbon atoms,R.sub.2 is hydrogen, halogen, unsubstituted or substituted C.sub.1 to C.sub.30 alkyl, unsubstituted or substituted aryl, arylalkyl, cycloalkyl with 3 to 7 carbon atoms, cyano, nitro, or a heterocyclic,R.sub.3 is hydrogen, halogen, unsubstituted or substituted C.sub.1 to C.sub.30 alkyl, unsubstituted or substituted aryl, arylalkyl, cycloalkyl with 3 to 7 carbon atoms, cyano, nitro, or a heterocyclic, andR.sub.4 is unsubstituted or substituted C.sub.1 to C.sub.30 alkyl, unsubstituted or substituted aryl, arylalkyl, cycloalkyl are 3 to 7 carbon atoms. Such vinyl tricarbonyl compound is effective against tumor cells.
    Type: Grant
    Filed: October 19, 1987
    Date of Patent: May 29, 1990
    Assignee: Yale University
    Inventors: Harry H. Wasserman, Natesan Murugesan, John H. Van Duzer
  • Patent number: 4904819
    Abstract: Bicyclic sulfonamide derivatives represented by the formula: ##STR1## (wherein R.sub.1 is hydrogen or lower alkyl; R.sub.2 is lower alkyl, aralkyl, or aryl which may be substituted by lower alkyl, alkoxy, acetoxy, hydroxy, halogen, nitro or phenyl; and the wavy line indicates R or S configuration or their mixture) or their salt being used as antithrombotic, antivasoconstricting, and antibronchoconstricting drugs and the process therefor.
    Type: Grant
    Filed: April 28, 1988
    Date of Patent: February 27, 1990
    Assignee: Shionogi & Co., Ltd.
    Inventors: Sanji Hagishita, Kaoru Seno
  • Patent number: 4902818
    Abstract: The manufacture of optically active bifunctional compounds of the general formula ##STR1## wherein R represents protected hydroxymethyl, protected formyl or alkoxycarbonyl and R.sup.1 represents a group of the formula ##STR2## in which R.sup.2 and R.sup.3 represents lower alkyl or cycloalkyl or R.sup.2 and R.sup.3 together with the nitrogen atom represent a heterocyclic ring, by isomerizing compounds of the general formula ##STR3## wherein R, R.sup.2 and R.sup.3 have the above significance and R.sup.3 can additionally signify hydrogen, is described.The compounds of formula I are potential intermediates in the manufacture of, interalia, natural vitamin E and natural vitamin K.sub.1.
    Type: Grant
    Filed: October 5, 1988
    Date of Patent: February 20, 1990
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Hans-Jurgen Hansen, Rudolf Schmid, Max Schmid
  • Patent number: 4898977
    Abstract: The invention relates to novel processes and intermediates for the preparation of 5-amino-4-hydroxyvaleric acid derivatives of the formula ##STR1## in which R.sup.1 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl or the radical of a natural amino acid, R.sup.2 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl, amino, hydroxy, mercapto, sulphinyl, sulphonyl or the radical of a natural amino acid, and R.sup.3 represents optionally substituted hydroxy or amino, by sigmatropic rearrangement of a suitable allyl ester, halolactonisation of the resulting .gamma.,.delta.-unsaturated acid or of a suitable derivative thereof, exchange of halogen for a nitrogen-containing nucleophile, opening of the lactone ring and freeing of the amino group. Compounds of the formula I are starting materials for the preparation of renin-inhibitors which have an anti-hypertensive action.
    Type: Grant
    Filed: August 13, 1987
    Date of Patent: February 6, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Herold, Christof Angst
  • Patent number: 4897473
    Abstract: This invention produces higher homologs, i.e., differing by at least a --CH.sub.2 -unit, of carbonyloxy-containing compounds by treating the carbonyloxy-containing compounds with carbon monoxide and hydrogen in the presence of a ruthenium-containing compound, a proton donor, an iodide promoter, and optionally, a manganese-containing compound.
    Type: Grant
    Filed: May 1, 1981
    Date of Patent: January 30, 1990
    Assignee: Union Carbide Chemicals and Plastics Company Inc.
    Inventor: Bernard D. Dombek
  • 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: 4892965
    Abstract: 3,3'-Thiobis(2,5-dihydrothiophene-1,1-dioxides) on heating with a reactive Diels-Alder dienophile undergo a reaction producing thioethers having two six-membered alicyclic rings in the molecule, such as 4,4'-thiobis(3,6-dihydrophthalic acids) of the esters, anhydrides or imides thereof, and 4,4'-thiobis(1,2,3,6- tetrahydrophthalic adics) or the esters, anhydrides or imides thereof. Both rings of the dihydrothiophene dioxides participate in the reaction, apparently by forming a tetraene structure which co-reacts with two equivalents of the dienophile to form an adduct in which each six-membered ring has one or two olefinic double bonds. During the course of the reaction, the thioether bridge remains intact. Some of the bis(alicyclic) thioethers are readily converted to the corresponding bis(aromatic)thioethers by use of known aromatization methods and systems. Various utilities for the products of the foregoing reactions are described.
    Type: Grant
    Filed: June 6, 1988
    Date of Patent: January 9, 1990
    Assignee: Ethyl Corporation
    Inventor: G. Patrick Stahly
  • Patent number: 4888358
    Abstract: Novel 13,14-dihydroprostaglandin derivatives of the formula ##STR1## wherein: m is 1 or 3;R.sub.1 is hydrogen or alkyl;R.sub.2 is hydrogen or lower alkyl;R.sub.3 and R.sub.4 are independently hydrogen or methyl;R.sub.5 is alkyl, CF.sub.3 (CH.sub.2).sub.n -- in which n is an integer of 3-5, cycloalkyl, or optionally substituted phenyl, benzyl or phenoxy; orR.sub.4 and R.sub.5 taken together with the carbon to which they are attached is cycloalkyl of 4-8 carbon atoms;X is cis --CH.dbd.CH-- or --CH.sub.2 CH.sub.2 -- when m is 3, orX is --CH.sub.2 CH.dbd.C.dbd.CH-- when m is 1;and the wavy lines represent the .alpha. or .beta. configuration with the proviso that when one wavy line is .alpha. the other is .beta.;or a pharmaceutically acceptable salt thereof,have been prepared. They are useful in particular for their antihypertensive and anti-ulcerogenic properties.
    Type: Grant
    Filed: August 25, 1988
    Date of Patent: December 19, 1989
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Joan Huguet, Joseph M. Muchowski, Maria T. Lara
  • Patent number: 4882341
    Abstract: The invention relates to amino substituted propenoates and their use against fungi.
    Type: Grant
    Filed: September 9, 1988
    Date of Patent: November 21, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: John M. Clough, Ian T. Kay