Bicyclo Ring System Having The Hetero Ring As One Of The Cyclos Patents (Class 549/355)
  • Patent number: 4745198
    Abstract: The invention concerns novel 4-phenyl-1,3-dioxan-5-ylalkenoic acid derivatives of the formula I having cis relative stereochemistry at positions 4 and 5 of the dioxane ring and wherein Ra and Rb are variously hydrogen, alkyl, halogenoalkyl, alkenyl, and optionally substituted aryl or arylalkyl, Rc is hydroxy, alkoxy or alkanesulphonamido, n is 1 or 2, A is ethylene or vinylene, Y is (2-5C)polymethylene optionally substituted by alkyl, and benzene ring B is optionally substituted phenyl, or, when Rc is hydroxy, a salt thereof. The acid derivatives antagonize one or more of the actions of thromboxane A.sub.2 (TXA.sub.2) and are expected to be of value in those disease conditions in which TXA.sub.2 is involved. The invention also provides pharmaceutical compositions containing an acid derivative of formula I, and processes for their chemical production.
    Type: Grant
    Filed: November 12, 1985
    Date of Patent: May 17, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: Andrew G. Brewster, Peter W. R. Caulkett
  • Patent number: 4736031
    Abstract: Novel condensed seven-membered heterocyclic compounds of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are independently hydrogen, halogen, hydroxy, lower alkyl or lower alkoxy,R.sub.3 and R.sub.4 are independently hydrogen, optionally substituted lower alkyl, optionally substituted cycloalkyl or optionally substituted aralkyl, or both jointly form an optionally substituted ring together with the adjacent nitrogen atom,X is hydrogen, optionally substituted lower alkyl, optionally substituted aryl or a carboxyl group which may be esterified or amidated,Y is >C.dbd.O or >CH--OR.sub.5 in which R.sub.5 is hydrogen, acyl or optionally substituted carbamoyl,A is oxygen atom or sulfur atom, E is oxygen atom or methylene, andG is lower alkylene, provided that when A is sulfur atom, E is methylene,and salts thereof exhibit serotonin S.sub.
    Type: Grant
    Filed: April 15, 1986
    Date of Patent: April 5, 1988
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hirosada Sugihara, Minoru Hirata
  • Patent number: 4701466
    Abstract: Compounds of general formula ##STR1## in which R.sub.1, taken separately, denotes a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group, andR.sub.2, taken separately, denotes a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group or a phenylthio or phenylsulphonyl group, or alternativelyR.sub.1 and R.sub.2 together form an ethano bridge or, together with the two carbon atoms 8 and 9, form a fused benzene ring,R.sub.3 denotes a hydrogen atom or a methyl group andR.sub.4 denotes a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group or a cation of a base which is acceptable in pharmacology, the group CH(R.sub.3)COOR.sub.4 being at position 2 or 3. have uses in treatment of inflammation, pain and undesirable platelet aggregation.
    Type: Grant
    Filed: April 10, 1986
    Date of Patent: October 20, 1987
    Assignee: Synthelabo
    Inventors: Thomas Purcell, Lydia Zard
  • Patent number: 4672062
    Abstract: 3-amino-2,3-dihydro-1-benzoxepine compounds corresponding to the general Formula I ##STR1## wherein R.sub.1 and R.sub.2 may each be hydrogen, halogen, lower alkyl or lower alkoxy, or if one of R.sub.1 and R.sub.2 is hydrogen, the other may also be nitro or trifluoromethyl, R.sub.3 represents hydrogen or a lower alkyl group which optionally may be substituted by hydroxy, lower alnoxy, an optionally substituted phenyl group or an optionally substituted amino group, and R.sub.4 represents hydrogen or lower alkyl, or R.sub.3 and R.sub.4 together with the nitrogen atom form a 5 or 6 member heterocycle. The compounds exhibit pharmacological, especially antidepressive, activity.
    Type: Grant
    Filed: November 4, 1985
    Date of Patent: June 9, 1987
    Assignee: Kali-Chemie Pharma GmbH
    Inventors: Heinrich-Wilhelm Ohlendorf, Michael Ruhland, Klaus-Ullrich Wolf
  • Patent number: 4670041
    Abstract: Compounds of the formula ##STR1## wherein X is (--CR.sub.4 R.sub.4 --).sub.m in which m is 0 or 1;Y is (--CR.sub.5 R.sub.6 --).sub.n in which n is 0, 1 or 2;Z is (--CR.sub.7 R.sub.7 --).sub.p in which p is 1, 2, or 3; the sum of m+n+p is an integer of 2 to 5, inclusive;R.sub.2 and R.sub.3 each is H or alkyl, and the like;R.sub.1 is H or alkyl; andW is an unsaturated moiety, are useful as plant growth regulators and herbicides.
    Type: Grant
    Filed: September 13, 1982
    Date of Patent: June 2, 1987
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: George B. Payne, Samuel B. Soloway, James E. Powell, Steven A. Roman, Willy D. Kollmeyer
  • Patent number: 4609743
    Abstract: A process for the production of the beetle aggregation pheromone brevicomin comprising reacting acrolein dimer sequentially with ethyllithium, a methylating agent and aqueous protonic acid. In a modification of the process the acrolein dimer is reacted with ethyl Grignard reagent prior to reaction with an alkyllithium compound. The process includes distributing the brevicomin product to areas to be controlled for beetles.
    Type: Grant
    Filed: April 17, 1984
    Date of Patent: September 2, 1986
    Assignee: University of Pittsburgh
    Inventors: Theodore Cohen, Mahadevan Bhupathy
  • Patent number: 4563458
    Abstract: The invention relates to substituted 4-aminomethylene-chromans and chromens of Formula (I) infra, as well as methods for making of said chromans and chromens, compositions containing said chromans and chromens and methods for the use of said chromans, chromens and compositions containing said chromans and chromens. The compounds and compositions of the invention are useful for their circulation influencing activity.
    Type: Grant
    Filed: December 13, 1983
    Date of Patent: January 7, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Arno Widdig, Hans-Joachim Kabbe, Andreas Knorr, Ulrich Benz
  • Patent number: 4563476
    Abstract: Substituted 5-hydroxy-2,3-dihydrobenzofuran and analogs such as the substituted 6-hydroxy-2,3-dihydrobenzopyrans were prepared from an appropriately substituted (5-hydroxy-2,3-dihydrobenzofuran-6-yl) formaldehyde or analog thereof with an aryl amine followed by reduction. These compounds were found to be potent topical anti-inflammatory agents.
    Type: Grant
    Filed: November 21, 1983
    Date of Patent: January 7, 1986
    Assignee: Merck & Co., Inc.
    Inventors: Michael N. Chang, Milton L. Hammond, Norman P. Jensen, Robert A. Zambias
  • Patent number: 4556656
    Abstract: Isochromans, isothiochromans, 2-benzoxepins, and 2-benzothiepins are described. The compounds possess hypotensive and anti-psychotic properties; methods and compositions using them are described.
    Type: Grant
    Filed: April 4, 1979
    Date of Patent: December 3, 1985
    Assignee: The Upjohn Company
    Inventor: John M. McCall
  • Patent number: 4548929
    Abstract: Novel heterobicyclic compounds of Formula I, processes for preparing same and pesticidal compositions and methods are described.
    Type: Grant
    Filed: April 18, 1983
    Date of Patent: October 22, 1985
    Assignee: SDS Biotech Corporation
    Inventors: Thomas A. Magee, Robert D. Battershell, Lawrence E. Limpel, Andrew W. Ho, Arthur W. Friedman, H. Glenn Corkins, William W. Brand, Russell Buchman, Louis Storace, Edmond R. Osgood
  • Patent number: 4529806
    Abstract: Novel compounds of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are H or alkyl and R is an optionally-substituted unsaturated, cycloalkyl, secondary-alkyl, aromatic or heterocyclic group, are useful as plant growth regulators and herbicides. Certain intermediates are also novel.
    Type: Grant
    Filed: April 9, 1984
    Date of Patent: July 16, 1985
    Assignee: Shell Oil Company
    Inventors: Herbert Estreicher, George B. Payne
  • Patent number: 4521607
    Abstract: New bicyclic compounds, inclusive of salts thereof, of the formula: ##STR1## wherein R.sup.1 and R.sup.2, which may be the same or different, each represent hydrogen, halogen, lower alkyl, hydroxyl, lower alkyloxy or aralkyloxy, or R.sup.1 and R.sup.2 jointly represent lower alkylenedioxy; R.sup.3 and R.sup.4 each represent hydrogen or lower alkyl; R.sup.5 represents hydrogen, lower alkyl or --CH.sub.2 SR.sup.7 (R.sup.7 represents hydrogen or acyl); R.sup.6 represents hydrogen or acyl, or R.sup.6 and R.sup.7 jointly represent a single bond; X represents --CH.sub.2 --, --O-- or >N--R.sup.8 (R.sup.8 represents hydrogen, acyl or lower alkyl); and n represents 2, 3 or 4, have inhibitory activities of angiotensin converting enzyme and bradykinin decomposing enzyme, and are useful as antihypertensive agents.
    Type: Grant
    Filed: April 2, 1982
    Date of Patent: June 4, 1985
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Yoshikazu Oka, Kohei Nishikawa, Akio Miyake
  • Patent number: 4511391
    Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: X is selected from halogen, nitro, cyano, alkyl, substituted alkyl, alkenyl, alkynyl, hydroxy, alkoxy, substituted alkoxy, alkenyloxy, alkynyloxy, alkanoyloxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, sulfamoyl, substituted sulfamoyl, benzyloxy, substituted benzyloxy, amino, substituted amino, and the groups formyl and alkanoyl and the oxime, imine and Schiff base derivatives thereof;Y and Z are independently selected from methylene, oxygen and sulfur provided that at least one of Y and Z is selected from oxygen and sulfur;R.sup.1 is selected from hydrogen, alkyl, alkenyl alkynyl, substituted alkyl, acyl, alkylsulfonyl, benzenesulfonyl, substituted benzenesulfonyl, and an inorganic or organic cation;R.sup.2 is selected from alkyl, alkenyl, alkynyl, substituted alkyl, haloalkenyl and haloalkynyl;R.sup.3 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl and phenyl;R.sup.4 is selected from hydrogen, halogen, cyano, C.
    Type: Grant
    Filed: May 24, 1983
    Date of Patent: April 16, 1985
    Assignee: ICI Australia Limited
    Inventors: Alexander Serban, Keith G. Watson, Graham J. Bird, Graeme J. Farquharson
  • Patent number: 4504304
    Abstract: Novel compounds of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are H or alkyl and R is an optionally-substituted unsaturated, cycloalkyl, secondary-alkyl, aromatic or heterocyclic group, are useful as plant growth regulators and herbicides. Certain intermediates are also novel.
    Type: Grant
    Filed: August 29, 1983
    Date of Patent: March 12, 1985
    Assignee: Shell Oil Company
    Inventors: Herbert Estreicher, George B. Payne
  • Patent number: 4480107
    Abstract: Process for the preparation of muscone starting from pyranic derivatives by treatments thereof with hydrogen in an inert organic solvent and in the presence of a noble metal catalyst. Compounds of formula ##STR1## and process for its preparation via dehydrogenation and dehydration of corresponding diol. Process for the preparation of unsaturated macrocyclic ketones of formula ##STR2## wherein the dotted lines stand for a single or a double bondwhereinx=1 and y=2, orx=2 and y=1, starting from compound (Ia) via acidic treatment.
    Type: Grant
    Filed: November 20, 1981
    Date of Patent: October 30, 1984
    Assignee: Firmenich SA
    Inventors: Karl H. Schulte-Elte, Joseph J. Becker, Walter Schenk
  • Patent number: 4436749
    Abstract: A compound corresponding to formula (I): ##STR1## wherein X represents oxygen, sulphur or >N--R',R' representing hydrogen or an alkyl radical,R.sub.1 to R.sub.4, andR'.sub.1 to R'.sub.5 independently represent the following:a hydrogen or halogen atom,an alkyl, aryl, alkoxy, aryloxy or acyloxy radical,a hydroxy radical,an amino, mono-alkylamino or di-alkylamino radical,a hydroxyalkyl, aminoalkoxy, mono- or di-alkylaminoalkoxy radical,in the form of the d or l isomer, or in the form of a racemic mixture, is useful as a medicament.
    Type: Grant
    Filed: May 10, 1982
    Date of Patent: March 13, 1984
    Assignee: Pierre Fabre S.A.
    Inventors: Philippe Hatinguais, Jean-Francois Patoiseau, Gilbert Marcelon
  • Patent number: 4426535
    Abstract: A method of producing synthetic brevicomin by direct distillation and a method of using the same in interfering with normal propagation of Dendroctonus beetles.
    Type: Grant
    Filed: October 20, 1981
    Date of Patent: January 17, 1984
    Assignee: University of Pittsburgh
    Inventors: Theodore Cohen, James Matz
  • Patent number: 4341897
    Abstract: New process for the preparation of muscone, a valuable macrocyclic musky perfume ingredient. The process makes use of an .alpha.,.omega.-dialdehyde as starting material.
    Type: Grant
    Filed: March 30, 1981
    Date of Patent: July 27, 1982
    Assignee: Firmenich SA
    Inventors: Karl-Heinrich Schulte-Elte, Arnold Hauser, Gunther Ohloff
  • Patent number: 4338316
    Abstract: The disclosure relates to 9.beta.-aryloxy prostane derivatives, for example 16-(3-chlorophenoxy)-11.alpha.,15.alpha.-dihydroxy-16-methyl-9.beta.-pheno xy-18,19,20-trinor-5-cis,13-trans-prostadienoic acid, which possess high activity as abortifacients, cervical softeners, inducers of parturition or inhibitors of gastric acid production in mammals. These properties are typical of prostaglandin analogues of the E series, but chemically the new 9.beta.-aryloxy prostane derivatives are prostaglandin F series analogues and are therefore more stable than the E series analogues previously used for the above purposes. The new derivatives are manufactured by known analogy processes, and are formulated in conventional manner.
    Type: Grant
    Filed: September 26, 1979
    Date of Patent: July 6, 1982
    Assignee: Imperial Chemical Industries Limited
    Inventor: Peter R. Marsham
  • Patent number: 4335262
    Abstract: Process for the preparation of muscone starting from pyranic derivatives by treatments thereof with hydrogen in an inert organic solvent and in the presence of a noble metal catalyst.Compound of formula ##STR1## and process for its preparation via dehydrogenation and dehydration of corresponding diol.Process for the preparation of unsaturated macrocyclic ketones of formula ##STR2## wherein the dotted lines stand for a single or a double bond wherein x=1 and y=2, orx=2 and y=1,starting from compound (Ia) via acidic treatment.
    Type: Grant
    Filed: September 3, 1980
    Date of Patent: June 15, 1982
    Assignee: Firmenich SA
    Inventors: Karl H. Schulte-Elte, Joseph J. Becker, Walter Schenk