Additional Polycyclo Heterocyclic Ring System Attached Directly Or Indirectly To The Bicyclo Ring System By Nonionic Bonding Patents (Class 548/454)
  • Patent number: 4881967
    Abstract: This invention pertains to novel heterocyclic 2,3-dihydrobenzofuran and chromane compounds, including stereoisomers, agriculturally suitable composition containing them, and their use as broad spectrum herbicides.
    Type: Grant
    Filed: June 2, 1988
    Date of Patent: November 21, 1989
    Assignee: E. I. Du Pont De Nemours and Company
    Inventor: Joseph E. Semple
  • Patent number: 4879293
    Abstract: The compound of the formula ##STR1## wherein X is a cyclic group which may optionally be substituted; Y is a carboxyl group which may optionally be esterified or amidated; Z is --CH.dbd.CH--CH.dbd.CH--, --S--(CH.sub.2).sub.l --S-- is an integer of 1 to 3), --N.dbd.CH--CH.dbd.N-- or --(CH.sub.2).sub.m --(m is an integer of 3 to 5); ring A may optionally be substituted with halogen, nitro, amino, alkanoylamino, alkoxycarbonyl, carboxyl or carbamoyl; and n is an integer of 1 to 3, and salts thereof. The compounds display a strong antianxiety effect to mammalian animals and are useful for the prevention or treatment of a disease such as psychoromatic disease and anxiety neurosis.
    Type: Grant
    Filed: September 8, 1988
    Date of Patent: November 7, 1989
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Kentaro Hiraga, Yoshiaki Saji
  • Patent number: 4874759
    Abstract: Hydroxyindole-3-carboxylic acid amide compounds of the general formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are, the same or different, respectively a hydrogen atom, an alkyl group, an aryl group, an aralkyl group or a heteroaryl group, or R.sup.1 and R.sup.2 and/or R.sup.3 and R.sup.4 are respectively groups which are combined to each other taken together with the adjacent nitrogen atom to form a heterocyclic group, R.sup.5 is an alkyl group, R.sup.6 is a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or an aralkyl group and X is a hydrogen atom, a halogen atom or a lower alkanoyl group, or their acid addition salts.These compounds are of use as diuretics or a therapeutic medicine for circulation system diseases.
    Type: Grant
    Filed: September 23, 1988
    Date of Patent: October 17, 1989
    Assignee: Yoshitomi Pharmaceutical Industries, Ltd.
    Inventors: Tetsuya Tahara, Tsuguo Ikebe, Ichiro Hakamada, Osamu Yaoka
  • Patent number: 4868315
    Abstract: This invention relates to aryloxycycloalkanolaminoalkylene aryl ketones to the processes for their preparation and to their use as antihypertensive agents.
    Type: Grant
    Filed: January 11, 1988
    Date of Patent: September 19, 1989
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Michael E. LeTourneau, James R. McCarthy, Donald L. Trepanier
  • Patent number: 4866087
    Abstract: Carboxyalkyl urea compounds and derivatives thereof are disclosed which are useful as angiotensin converting enzyme (ACE) inhibitors and as antihypertensives. These compounds and derivatives are represented by the general formula: ##STR1## An illustrative specie falling within this general formula is:N-(2-carboxy-4-phenylbutyl-N-isopropylaminocarbonyl-L-tryptophan.
    Type: Grant
    Filed: June 27, 1983
    Date of Patent: September 12, 1989
    Assignee: Merck & Co., Inc.
    Inventors: William J. Greenlee, David G. Hangauer, Jr., Arthur A. Patchett
  • Patent number: 4833254
    Abstract: Novel heteroarotinoid compositions characterized by the formulae: ##STR1## where: X is S or O; OAc is the acetate group ##STR2## and R is --H, --OH, --OCH.sub.3, or --OC.sub.2 H.sub.5 and includes ##STR3## for formulae (1) and (2). Such compositions exhibit activity as anticancer agents.
    Type: Grant
    Filed: May 11, 1987
    Date of Patent: May 23, 1989
    Assignee: The Board of Regents for the Oklahoma Agricultural and Mechanical Colleges acting for and on behalf of Oklahoma State University
    Inventors: Kenneth D. Berlin, Warren T. Ford, Shirish N. Rajadhyaksha, Jonathan B. Gale, Lyle W. Spruce
  • Patent number: 4826838
    Abstract: Carbocyclic and heterocyclic carbonylmethylene- and carbonylmethylpiperidines and -pyrrolidines are serotonin antagonists.
    Type: Grant
    Filed: July 7, 1987
    Date of Patent: May 2, 1989
    Assignee: Sandoz Ltd.
    Inventors: Brian P. Richardson, Rudolf K. A. Giger, Gunter Engel, Roland Furler
  • Patent number: 4814345
    Abstract: Novel 1-phenyl-2-aminocarbonylindole compounds are disclosed having the general formula I ##STR1## wherein R.sub.1 is an aliphatic or aromatic acyl group or an optionally substituted benzyl group; R.sub.2 is hydrogen or a lower alkyl radical; R.sub.3 is a hydrogen, a halogen, a lower alkyl radical, or a lower alkoxy radical; R.sub.4 is hydrogen, a halogen, a lower alkyl radical, or a lower alkoxy radical; R.sub.5 has the significance given R.sub.3 ; R.sub.6 has the significance given for R.sub.4, or R.sub.6 is nitro or trifluoromethyl; R.sub.7 and R.sub.8 each represent hydrogen or a lower alkyl radical, or together with a nitrogen atom form a heterocyclic group; and Z signifies an alkylene chain optionally substituted by hydroxy or acyloxy. The compounds have pharmacological, in particular antiarrhythmic, properties.
    Type: Grant
    Filed: November 20, 1987
    Date of Patent: March 21, 1989
    Assignee: Kali-Chemie Pharma GmbH
    Inventors: Heinrich-Wilhelm Ohlendorf, Wilhelm Kaupmann, Ulrich Kuhl, Gerd Buschmann, Stephen J. Magda
  • Patent number: 4803198
    Abstract: New 1-phenyl-2-aminocarbonylindole compounds are described which have the general formula I ##STR1## where R.sub.1 is a hydrogen atom, or a lower alkyl, alkenyl, cycloalkylalkyl radical, R.sub.2 is a hydrogen atom or a lower alkyl radical, R.sub.3 is a hydrogen or halogen atom, or a lower alkyl, hydroxyl or lower alkoxy radical, R.sub.4 is a hydrogen or halogen atom, or a lower alkyl, hydroxyl or lower alkoxy radical, or, if R.sub.3 is a hydrogen atom, R.sub.4 may be a nitro or trifluoromethyl radical, or R.sub.3 and R.sub.4 together denote a methylenedioxy or ethylenedioxy radical, R.sub.5 has the meanings given for R.sub.3, R.sub.6 has the meanings given for R.sub.4, R.sub.7 is a hydrogen atom or, if R.sub.5 and R.sub.6 are lower alkoxy radicals, R.sub.7 may also be a lower alkoxy radical, R.sub.8 and R.sub.9 are each a hydrogen atom or a lower alkyl radical or, together with the nitrogen atom, form a heterocyclic group, and Z is an alkylene chain which is optionally substituted by hydroxyl.
    Type: Grant
    Filed: July 15, 1986
    Date of Patent: February 7, 1989
    Assignee: Kali-Chemie Pharma GmbH
    Inventors: Heinrich-Wilhelm Ohlendorf, Wilhelm Kaupmann, Ulrich Kuehl, Gerd Buschmann, Stephen J. Magda
  • Patent number: 4782083
    Abstract: Compounds of formula (I) and pharmaceutically acceptable salts thereof: ##STR1## wherein: one of R.sub.1 and R.sub.2 is hydrogen or C.sub.1-4 alkyl and the other is C.sub.1-4 alkyl or R.sub.1 and R.sub.2 together are C.sub.2-5 -polymethylene;either R.sub.3 is hydrogen, hydroxy, C.sub.1-6 alkoxy or C.sub.1-7 acyloxy and R.sub.4 is hydrogen or R.sub.3 and R.sub.4 together are a bond;R.sub.5 is hydrogen C.sub.1-6 alkyl optionally substituted by halogen hydroxy, C.sub.1-6 alkoxy, C.sub.1-6 alkoxycarbonyl, carboxy or amino optionally substituted by one or two independent C.sub.1-6 alkyl groups, or C.sub.2-6 alkenyl, amino optionally substituted by a C.sub.1-6 alkyl or C.sub.1-6 alkenyl group or by a C.sub.1-6 alkanoyl group optionally substituted by up to three halo atoms, by a phenyl group optionally substituted by C.sub.1-6 alkyl, C.sub.1-6 alkoxy or halogen, or aryl or hetroaryl, either being optionally substituted by one or more groups or atoms selected from the class of C.sub.1-6 alkyl, C.sub.
    Type: Grant
    Filed: August 29, 1986
    Date of Patent: November 1, 1988
    Assignee: Beecham Group P.L.C.
    Inventors: Frederick Cassidy, Geoffrey Stemp, John M. Evans
  • Patent number: 4757151
    Abstract: Certain 2-substituted-[2-substituted-amino]-N-arylalkyl-3-[indol-3-yl]propanamides demonstrate activity as appetite suppressants. The compounds, pharmaceutical compositions, and a method of suppressing appetite are disclosed.
    Type: Grant
    Filed: September 30, 1986
    Date of Patent: July 12, 1988
    Assignee: Warner-Lambert Company
    Inventor: David C. Horwell
  • Patent number: 4751316
    Abstract: Novel 1,5-benzoxathiepin derivatives 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 or 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 (wherein R.sub.5 is hydrogen, acyl or optionally substituted carbamoyl); m is an integer of 0 to 2; n is an integer of 1 to 6] and salts thereof exhibit serotonin S.sub.
    Type: Grant
    Filed: April 15, 1987
    Date of Patent: June 14, 1988
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hirosada Sugihara, Minoru Hirata
  • Patent number: 4746747
    Abstract: There is provided a novel anisole derivative represented by the following formula (I): ##STR1## wherein A to D are defined as follows: (1) A, B and C are each a hydrogen atom, and D represents --OH, a halogen atom, --CO.sub.2 R.sup.1 of which R.sup.1 represents a lower alkyl group, --SO.sub.2 R.sup.2 of which R.sup.2 represents a lower alkyl group, or ##STR2## or (2) A and C are each a hydrogen atom, B is --OH, and D represents --CO.sub.2 R.sup.3 of which R.sup.3 represents a lower alkyl group; or(3) A is a hydrogen atom, B and C form an oxo group .dbd.O together, and D represents --CO.sub.2 R.sup.4 of which R.sup.4 represents a lower alkyl group; or(4) B and C are each a hydrogen atom, D is a halogen atom, and A represents --CHO.
    Type: Grant
    Filed: August 28, 1986
    Date of Patent: May 24, 1988
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Yoshiharu Morita, Naoshi Imaki, Hisao Takayanagi, Yuki Takuma, Tadashi Shirasaka
  • Patent number: 4742067
    Abstract: Compounds of the formula ##STR1## are disclosed. These compounds are useful as hypotensive agents due to their angiotensin converting enzyme inhibition activity and depending upon the definition of X may also be useful as analgesics due to their enkephalinase inhibition activity.
    Type: Grant
    Filed: July 30, 1986
    Date of Patent: May 3, 1988
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Sesha I. Natarajan, Eric M. Gordon
  • Patent number: 4730062
    Abstract: Tetrafluorobenzofurans of the formula ##STR1## are prepared by contacting, at elevated temperature in an aprotic solvent, an ether of the formula ##STR2## with a catalytic mixture of metallic cooper and a polydentate or other ligand, wherein R.sup.1 is hydrogen, nitro, amino, phthalimido or acetylimido, R.sup.2 is at least one of hydrogen, halo, cyano, alkyl, hydroxy, alkoxy, acyl, acyloxy, alkoxycarbonyl, alkoxycarbonylalkyl, phenyl, phenyloxy, trifluoromethyl or dialkylamino. The products are intermediates in the preparation of pyrazoline insecticides.
    Type: Grant
    Filed: April 19, 1985
    Date of Patent: March 8, 1988
    Assignee: FMC Corporation
    Inventors: David E. Seelye, Ernest L. Plummer
  • Patent number: 4727160
    Abstract: Compounds of the formula I ##STR1## in which the carboxyl group on carbon atom 3 is orientated in the endo-position relative to the bicyclic ring system of cis-configuration, and in which R.sup.1 denotes hydrogen, allyl, vinyl or a side-chain of a naturally occurring .alpha.-aminoacid, which may be protected, R.sup.2 denotes hydrogen, alkyl, alkenyl or aralkyl, Y denotes hydrogen or hydroxyl and Z denotes hydrogen, or Y and Z together denote oxygen, and X denotes alkyl, alkenyl or cycloalkyl, or aryl which is optionally mono-, di- or tri-substituted by alkyl, alkoxy, hydroxyl, halogen, nitro, amino, alkylamino, dialkylamino or methylenedioxy, or denotes indol-3-yl, a process for their preparation, agents containing these compounds and their use.
    Type: Grant
    Filed: October 9, 1984
    Date of Patent: February 23, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Volker Teetz, Rolf Geiger, Hansjorg Urbach, Reinhard Becker, Bernward Scholkens
  • Patent number: 4721712
    Abstract: Certain 2-oxindole-1-carboxamide compounds having an acyl substituent at the 3-position, and also on the carboxamide nitrogen atom, are inhibitors of the cyclooxygenase (CO) and lipoxygenase (LO) enzymes, and are useful as analgesic agents and anti-inflammatory agents in mammalian subjects. These 2-oxindole-1-carboxamide compounds are of particular value for acute administration for ameliorating pain in human patients recovering from surgery or trauma, and also for chronic administration to human subjects for alleviating the symptoms of chronic diseases, such as rheumatoid arthritis and osteoarthritis. Certain 2-oxindole-1-carboxamide compounds unsubstituted at C-3, but having an acyl substituent on the carboxamide nitrogen atom, are useful as intermediates to the aforementioned analgesic and anti-inflammatory agents.
    Type: Grant
    Filed: November 13, 1984
    Date of Patent: January 26, 1988
    Assignee: Pfizer Inc.
    Inventor: Saul B. Kadin
  • Patent number: 4714709
    Abstract: N-(2,10-dioxa-tricyclo-[5,3,1,0.sup.3,8 ]-undecane-5-yl)-tryptamine compounds corresponding to the formula ##STR1## with blood-pressure lowering effects, a method of producing such compounds and pharmaceutical compositions incorporating such compounds, wherein R.sub.1 is hydrogen, a benzyl or lower alkyl group; R.sub.2 is a lower alkyl or lower alkanoyl group; R.sub.3 is hydrogen or a lower alkyl group; R.sub.4 is hydrogen, benzyloxy, hydroxy or a lower alkoxy group; R.sub.5 is hydrogen, benzyloxy, hydroxy or a lower alkoxy group; and A and B either are both hydrogen or together represent a bond between their respective carbons.
    Type: Grant
    Filed: September 24, 1984
    Date of Patent: December 22, 1987
    Assignee: Kali-Chemie Pharma GmbH
    Inventors: Peter W. Thies, Samuel David, Ulrich Kuehl, Gerd Buschmann, Peter Flecker
  • Patent number: 4713393
    Abstract: Phenylalkyl-2,3-dihydrobenzofurans and analogs were prepared by (1) nucleophilic substitution involving an appropriately substituted 2,3-dihydrobenzofuranol (or 2,3-dihydrobenzopyranol) and a cinnamylhalide followed by reduction; or (2) by Wittig reaction involving a halomethyl derivative of 2,3-dihydrobenzofuran (or 2,3-dihydrobenzopyran and an aryl or a heteroaryl aldehyde followed by reduction. These compounds were found to be potent anti-inflammatory agents.
    Type: Grant
    Filed: April 25, 1985
    Date of Patent: December 15, 1987
    Assignee: Merck & Co., Inc.
    Inventors: Michael N. Chang, Kathryn L. Thompson, David A. Boulton
  • Patent number: 4672064
    Abstract: Novel 1,5-benzoxathiepin derivatives 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 or 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 ##STR2## (wherein R.sub.5 is hydrogen, acyl or optionally substituted carbamoyl); m is an integer of 0 to 2; n is an integer of 1 to 6] and salts thereof exhibit serotonin S.sub.
    Type: Grant
    Filed: December 10, 1985
    Date of Patent: June 9, 1987
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hirosada Sugihara, Minoru Hirata
  • Patent number: 4658037
    Abstract: Certain 2-oxindole-1-carboxamide compounds having an acyl substituent at the 3-position, and also on the carboxamide nitrogen atom, are inhibitors of the cyclooxygenase (CO) and lipoxygenase (LO) enzymes, and are useful as analgesic agents and anti-inflammatory agents in mammalian subjects. Certain 2-oxindole compounds unsubstituted at the 1-position but having an acyl substituent at C-3 of the formula ##STR1## and the base salts thereof, wherein X is hydrogen, 5-fluoro, 5-chloro or 5-trifluoromethyl; Y is hydrogen, 6-fluoro, 6-chloro or 6-trifluoromethyl; and R.sup.1 is benzyl, furyl, thienyl or thienylmethyl; provided that when X and Y are both hydrogen, R.sup.1 is not benzyl are useful as intermediates to the aforementioned analgesic and anti-inflammatory agents.
    Type: Grant
    Filed: December 30, 1985
    Date of Patent: April 14, 1987
    Assignee: Pfizer Inc.
    Inventor: Saul B. Kadin
  • Patent number: 4638010
    Abstract: Compounds of the formula ##STR1## are disclosed. These compounds are useful as hypotensive agents due to their angiotensin converting enzyme inhibition activity and depending upon the definition of X may also be useful as analgesics due to their enkephalinase inhibition activity.
    Type: Grant
    Filed: February 28, 1985
    Date of Patent: January 20, 1987
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Harold N. Weller, III, Eric M. Gordon
  • Patent number: 4636522
    Abstract: Compounds of the formula ##STR1## wherein Z is oxygen or sulfur are disclosed. These compounds are useful as hypotensive agents due to their angiotensin converting enzyme inhibition activity and depending upon the definition of X may also be useful as analgesics due to their enkephalinase inhibition activity.
    Type: Grant
    Filed: March 22, 1985
    Date of Patent: January 13, 1987
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Eric M. Gordon
  • Patent number: 4634716
    Abstract: Compounds of the formula: ##STR1## where R.sup.3 is ##STR2## where n is 1-3 and the R.sup.a 's and R.sup.b 's are independently hydrogen or loweralkyl; and pharmaceutically acceptable salts thereof; are inhibitors or angiotensin I converting enzyme useful as antihypertensive agents.
    Type: Grant
    Filed: May 16, 1983
    Date of Patent: January 6, 1987
    Assignee: Merck & Co., Inc.
    Inventors: William H. Parsons, David Taub
  • Patent number: 4634776
    Abstract: 3-Arylcarbonyl- and 3-cycloalkylcarbonyl-1-aminoalkyl-1H-indoles, useful as analgesic, anti-rheumatic and anti-inflammatory agents, are prepared by reacting a 3-arylcarbonyl- or 3-cycloalkylcarbonylindole with an aminoalkyl halide in the presence of an acid-acceptor; by reacting a 1-aminoalkyl-1H-indole with an arylcarboxylic acid halide or a cycloalkanecarboxylic acid halide in the presence of a Lewis acid; or by reacting a 3-arylcarbonyl- or 3-cycloalkanecarbonyl-1-tosyloxyalkyl- or haloalkyl-1H-indole with an amine.
    Type: Grant
    Filed: December 19, 1985
    Date of Patent: January 6, 1987
    Assignee: Sterling Drug, Inc.
    Inventor: Malcolm R. Bell
  • Patent number: 4624962
    Abstract: Compounds of the formula I ##STR1## in which n denotes 0-3,R.sup.1 and R.sup.1' are the same or different and denote hydrogen, alkyl or alkenyl, phenyl or benzyl, each substituted as desired;R.sup.2 denotes hydrogen, alkyl or alkenyl;R.sup.3 denotes hydrogen, alkyl, hydroxyalkyl, alkoxyalkyl or aminoalkyl, alkanoylaminoalkyl, guanidinoalkyl, imidazolylalkyl, indolylalkyl, mercaptoalkyl or alkylthioalkyl, phenylalkyl, hydroxphenylalkyl, phenoxyalkyl or phenylthioalkyl, or R.sup.2 and R.sup.3, together with the C and N atoms carrying them, denote a saturated or unsaturated 4- to 8-membered monocyclic or 8- to 10-membered bicyclic isocycle or heterocycle, optionally monosubstituted or disubstituted by hydroxyl, alkoxy having 1 to 3 C atoms or alkyl,R.sup.4 denotes hydrogen, alkyl, alkenyl, alkadienyl, alkinyl, alkeninyl or alkadiinyl, cycloalkyl, phenyl, benzyl, phenethyl or phenylpropyl, each of which can be optionally monosubstituted or disubstituted;R.sup.5 denotes hydrogen or alkyl, hydroxyl or alkoxy andR.
    Type: Grant
    Filed: February 1, 1985
    Date of Patent: November 25, 1986
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Rainer Henning, Hansjorg Urbach, Rolf Geiger, Volker Teetz, Bernward Scholkens
  • Patent number: 4623729
    Abstract: Compounds of the formula ##STR1## are disclosed. These compounds are useful as hypotensive agents due to their angiotensin converting enzyme inhibition activity and depending upon the definition of X may also be useful as analgesics due to their enkephalinase inhibition activity.
    Type: Grant
    Filed: July 22, 1982
    Date of Patent: November 18, 1986
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Sesha I. Natarajan, Eric M. Gordon
  • Patent number: 4621092
    Abstract: Compounds of the formula ##STR1## are disclosed. These compounds are useful as hypotensive agents due to their angiotensin converting enzyme inhibition activity and depending upon the definition of X may also be useful as analgesics due to their enkephalinase inhibition activity.
    Type: Grant
    Filed: July 14, 1983
    Date of Patent: November 4, 1986
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Sesha I. Natarajan, Eric M. Gordon
  • Patent number: 4616021
    Abstract: A compound of formula (I): ##STR1## wherein: either one of R.sub.1 and R.sub.2 is hydrogen and the other is selected from the class of C.sub.1-6 alkylcarbonyl, C.sub.1-6 alkoxycarbonyl, C.sub.1-6 alkylcarbonyloxy, C.sub.1-6 alkylhydroxymethyl, nitro, cyano, chloro, trifluoromethyl, C.sub.1-6 alkylsulphinyl, C.sub.1-6 alkylsulphonyl, C.sub.1-6 alkoxysulphinyl, C.sub.1-6 alkoxysulphonyl, C.sub.1-6 alkylcarbonylamino, C.sub.1-6 alkoxycarbonylamino, C.sub.1-6 alkyl-thiocarbonyl, C.sub.1-6 alkoxy-thiocarbonyl, C.sub.1-6 alkyl-thiocarbonyloxy, 1-mercapto C.sub.2-7 alkyl, formyl, or aminosulphinyl, aminosulphonyl or aminocarbonyl, the amino moiety being optionally substituted by one or two C.sub.1-6 alkyl groups, or C.sub.1-6 alkylsulphinylamino, C.sub.1-6 alkylsulphonylamino, C.sub.1-6 alkoxysulphinylamino or C.sub.1-6 alkoxysulphonylamino, or ethylenyl terminally substituted by C.sub.1-6 alkylcarbonyl, nitro or cyano, or --C(C.sub.1-6 alkyl)NOH or --C(C.sub.1-6 alkyl)NNH.sub.2, or one of R.sub.1 and R.sub.
    Type: Grant
    Filed: April 12, 1985
    Date of Patent: October 7, 1986
    Assignee: Beecham Group p.l.c.
    Inventors: Valerie A. Ashwood, John M. Evans
  • Patent number: 4605667
    Abstract: Pesticidal water-soluble aminoacid sulfenylated carbamates useful as broad spectrum insecticides and miticides, particularly useful as systemic insecticides.
    Type: Grant
    Filed: March 29, 1985
    Date of Patent: August 12, 1986
    Assignee: Union Carbide Corporation
    Inventors: Chennupati K. Rao, Themistocles D. D'Silva
  • Patent number: 4604402
    Abstract: Compounds of the formula ##STR1## are disclosed. These compounds are useful as hypotensive agents due to their angiotensin converting enzyme inhibition activity and depending upon the definition of X may also be useful as analgesics due to their enkephalinase inhibition activity.
    Type: Grant
    Filed: March 30, 1984
    Date of Patent: August 5, 1986
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Jollie D. Godfrey, Jr., Eric M. Gordon, Sesha I. Natarajan
  • Patent number: 4581354
    Abstract: 3-Arylcarbonyl- and 3-cycloalkylcarbonyl-1-aminoalkyl-1H-indoles, useful as analgesic, anti-rheumatic and anti-inflammatory agents, are prepared by reacting a 3-arylcarbonyl- or 3-cycloalkylcarbonylindole with an aminoalkyl halide in the presence of an acid-acceptor; by reacting a 1-aminoalkyl-1H-indole with an arylcarboxylic acid halide or a cycloalkanecarboxylic acid halide in the presence of a Lewis acid; or by reacting a 3-arylcarbonyl- or 3-cycloalkanecarbonyl-1-tosyloxyalky- or haloalkyl-1H-indole with an amine.
    Type: Grant
    Filed: July 15, 1985
    Date of Patent: April 8, 1986
    Assignee: Sterling Drug Inc.
    Inventor: Malcolm R. Bell
  • Patent number: 4571425
    Abstract: A method is provided for making aromatic bis(ether anhydrides) by effecting an exchange reaction between aromatic bis(ether imide) and phthalic anhydride in the presence of water and an exchange catalyst. The separation and recovery of phthalimide and aromatic bis(ether anhydride) is achieved in a stripper-reactor using a vaporous mixture of water and the exchange catalyst.
    Type: Grant
    Filed: February 14, 1985
    Date of Patent: February 18, 1986
    Assignee: General Electric Company
    Inventor: James M. Silva
  • Patent number: 4571406
    Abstract: Compounds of formula (I): ##STR1## wherein: either one of R.sub.1 and R.sub.2 is hydrogen and the other is selected from the class of C.sub.1-6 alkylcarbonyl, C.sub.1-6 alkoxycarbonyl, C.sub.1-6 alkylcarbonyloxy, C.sub.1-6 alkylhydroxymethyl, nitro, cyano, chloro, trifluoromethyl, C.sub.1-6 alkylsulphinyl, C.sub.1-6 alkylsulphonyl, C.sub.1-6 alkoxysulphinyl, C.sub.1-6 alkoxysulphonyl, C.sub.1-6 alkylcarbonylamino, C.sub.1-6 alkoxycarbonylamino, C.sub.1-6 alkyl-thiocarbonyl, C.sub.1-6 alkoxy-thiocarbonyl, C.sub.1-6 alkyl-thiocarbonyloxy, 1-mercapto C.sub.2-7 alkyl, formyl or aminosulphinyl, aminosulphonyl or aminocarbonyl, the amino moiety being optionally substituted by one or two C.sub.1-6 alkyl groups, or C.sub.1-6 alkylsulphinylamino, C.sub.1-6 alkylsulphonylamino C.sub.1-6 alkoxysulphinylamino or C.sub.1-6 alkoxysulphonylamino, or ethylenyl terminally substituted by C.sub.1-6 alkylcarbonyl, nitro or cyano, or --C(C.sub.1-6 alkyl)NOH or --C(C.sub.1-6 alkyl)NNH.sub.2, or one of R.sub.1 and R.sub.
    Type: Grant
    Filed: May 16, 1984
    Date of Patent: February 18, 1986
    Assignee: Beecham Group p.l.c.
    Inventors: John M. Evans, Frederick Cassidy
  • Patent number: 4569942
    Abstract: Certain 2-oxindole-1-carboxamide compounds having an acyl substituent at the 3-position, and also further substituted on the carboxamide nitrogen by an alkyl, cycloalkyl, phenyl or substituted phenyl group, are inhibitors of the cyclooxygenase (CO) and lipoxygenase (LO) enzymes, and are useful as analgesic and antiinflammatory agents in mammalian subjects. These 2-oxindole-1-carboxamide compounds are of particular value for ameliorating pain in human patients recovering from surgery or trauma, and alleviating the symptoms of chronic diseases, such as rheumatoid arthritis and osteoarthritis, in human subjects.Certain 2-oxindole-1-carboxamide compounds unsubstituted at C-3, but having a substituent on the carboxamide nitrogen, are useful as intermediates to the analgesic and antiinflammatory agents of the invention.
    Type: Grant
    Filed: March 22, 1985
    Date of Patent: February 11, 1986
    Assignee: Pfizer Inc.
    Inventor: Saul B. Kadin
  • 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: 4558043
    Abstract: Benzofurans or 2,3-dihydrobenzofurans of the formula ##STR1## in which R.sub.1 represents hydrogen or an aliphatic radical,R.sub.2 represents an amino group disubstituted by a bivalent aliphatic radical which is optionally interrupted by at least one hetero atom,and the aromatic ring may be additionally substituted,and the salts thereof, have anti-inflammatory and/or analgesic activities.
    Type: Grant
    Filed: July 11, 1984
    Date of Patent: December 10, 1985
    Assignee: Ciba Geigy Corporation
    Inventors: Paul Wenk, Werner Breitenstein, Marcus Baumann
  • Patent number: 4505921
    Abstract: New sulfonylurea compounds of the formula: ##STR1## in which n is 1 or 2,R is thienyl, furyl, pyridyl or phenyl optionally mono or disubstituted,R.sub.1 and R.sub.2, the same or different, each are hydrogen, halogen, (C.sub.1 to C.sub.5)-alkyl, (C.sub.1 to C.sub.5)-alkoxy, or trifluoromethyl, or together represent --CH.sub.2 --O--CH.sub.2 --,R.sub.3 is hydrogen, or hydroxy, andR.sub.4 is (C.sub.1 to C.sub.5)-alkyl, (C.sub.3 to C.sub.8)-cycloalkyl or azacycloalkyl of the formula: ##STR2## in which p is zero or an integer from 1 to 5, or azabicycloalkyl of the formula: ##STR3## in which m is 1, 2, or 3. These new compounds and physiologically tolerable salts thereof may be used as medicines especially in the treatment of diabetes.
    Type: Grant
    Filed: September 6, 1983
    Date of Patent: March 19, 1985
    Assignee: ADIR, S.A.R.L.
    Inventors: Laszlo Beregi, Pierre Hugon, Jacques Duhault, Michelle Boulanger
  • Patent number: 4485242
    Abstract: 3-[(Alkoxy)(aryl or heteroaryl)methyl]-1H-indoles which are useful as color formers in pressure-sensitive carbonless duplicating systems and thermal marking systems are prepared by reacting 3-[(arylsulfonyl)(aryl or heteroaryl)methyl]-1H-indoles with alcohols in the presence of a base.
    Type: Grant
    Filed: July 30, 1981
    Date of Patent: November 27, 1984
    Assignee: Sterling Drug Inc.
    Inventors: Paul J. Schmidt, William M. Hung
  • Patent number: 4470932
    Abstract: Carboxylic acid anhydrides of the general formulaR--CO--O--CO--R' (I)in whichR and R' are identical or different and represent an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted cycloalkyl group having 3 to 12 carbon atoms or an optionally substituted aryl group, or represent an optionally substituted 5-membered or 6-membered heterocyclic radical which additionally can be fused to a benzene ring,are obtained in high yields by a process in which a trimethylsilyl carboxylate of the general formulaR--CO--OSi(CH.sub.3).sub.3 (II)in whichR has the meaning given above, is reacted with a carboxylic acid-halide of the general formulaR'CO--X (III)in whichR' has the meaning given above, andX represents a halogen atom, if appropriate in the presence of a catalyst and, if appropriate, in the presence of a diluent, at a temperature between 20.degree. and 250.degree. C.The carboxylic acid anhydrides are valuable intermediate products for organic syntheses.
    Type: Grant
    Filed: October 22, 1982
    Date of Patent: September 11, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventor: Kurt Findeisen
  • Patent number: 4435419
    Abstract: The present invention concerns certain novel substituted 3-azabicyclo[3.1.0]hexanes and a method of treating depression and stress in a warm-blooded animal, comprising the administration of substituted 3-azabicyclo[3.1.0]hexanes.
    Type: Grant
    Filed: May 10, 1982
    Date of Patent: March 6, 1984
    Assignee: American Cyanamid Company
    Inventors: Joseph W. Epstein, Arnold C. Osterberg, Herbert J. Brabander
  • Patent number: 4428977
    Abstract: A water soluble composition including an amine or ammonium salt of a polyimide precursor which is obtained by the reaction steps of: reacting a tetracarboxylic compound and a diamine in about equimolar amounts in a water miscible organic solvent to obtain the polyimide precursor; and reacting the polyimide precursor with ammonia, or an aqueous solution of ammonia, or a primary or secondary aliphatic amine in an amount sufficient to neutralize the free carboxyl groups of the polyimide precursor.A process of coating and a substrate are also disclosed.
    Type: Grant
    Filed: September 24, 1976
    Date of Patent: January 31, 1984
    Assignee: General Electric Company
    Inventor: Marvin A. Peterson
  • Patent number: 4418061
    Abstract: A secalonic acid derivative of the formula (I); ##STR1## wherein R is ##STR2## wherein R.sub.1 and R.sub.2 each independently is a hydrogen atom or a C.sub.1-4 alkyl group; R.sub.3 is a hydrogen atom, a C.sub.1-4 alkyl group, an aryl group, a C.sub.1-5 alkoxy group, a halogen atom, a cyano group, a carboxyl group, a sulfonic acid group, a carboxylic acid amide group or a sulfonic acid amide group; and R.sub.4 is a saturated or unsaturated C.sub.1-22 alkyl group, an aryl group or an aryl alkyl group, and may have a substituent;and the pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: April 7, 1982
    Date of Patent: November 29, 1983
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Mitsuru Shibukawa, Chisei Shibuya, Kunihiko Ishii
  • Patent number: 4405788
    Abstract: There are described novel dye compounds which are represented by the formula ##STR1## wherein A is ##STR2## X is H, alkyl, aryl such as phenyl or naphthyl, or substituted aryl; W is H or alkyl; R is H or alkyl; Z and Y are each H or monovalent radicals; l and p are each 1 or 2 and m and n are each integers of from 2-6.
    Type: Grant
    Filed: December 26, 1979
    Date of Patent: September 20, 1983
    Assignee: Polaroid Corporation
    Inventors: Louis Locatell, Jr., Charles M. Zepp, Ronald F. Cieciuch
  • Patent number: 4396550
    Abstract: Novel dibenz [b,e] oxepin derivatives represented by the general formula: ##STR1## wherein R.sub.11 represents an alkyl group containing 1 to 5 carbon atoms, an alkoxy group containing 1 to 5 carbon atoms, a halogen atom, a cyclohexyl group or a phenyl group; and R.sub.21 represents ##STR2## wherein X represents a hydrogen atom, a hydroxy group, an amino group or a substituted aralkyl group containing 7 to 20 carbon atoms, and n represents 0 or an integer of 1 to 3 ##STR3## or (3) --NH--(CH.sub.2).sub.n --Y, wherein Y represents an alkylamino group containing 1 to 5 carbon atoms, an aralkyl group containing 7 to 20 carbon atoms, a substituted aralkyl group, an aralkyloxy group containing 7 to 20 carbon atoms, an aralkylamino group containing 7 to 20 carbon atoms, a heterocyclic ring or a substituted heterocyclic ring, and n has the same meaning as defined before; provided that when R.sub.
    Type: Grant
    Filed: April 21, 1981
    Date of Patent: August 2, 1983
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Hiroshi Takizawa, Osamu Morita, Yoshimasa Oiji, Tamotsu Hashimoto
  • Patent number: 4377525
    Abstract: Novel, unsaturated diacetylene-terminated polyimides and processes for their preparation are disclosed herein. These new polyimides are derivatives of anhydride-terminated aromatic polyimides from which they can be prepared by amidation to provide new unsaturated amide groups having a terminal group containing the structure --C.tbd.C--C.tbd.C--, hereinafter sometimes referred to as "conjugated diynes". These new compositions are more tractable than the original anhydride-terminated polyimides and can be converted at appropriate lower temperatures to crosslinked, insoluble, infusible polymers without by-product formation, thereby extending greatly the applications for which the aromatic polyimides can be employed. Moreover, these new polyimides can undergo the Diels-Alder type of addition with a large number of dienophiles. Certain monomeric materials are also described.
    Type: Grant
    Filed: March 2, 1982
    Date of Patent: March 22, 1983
    Assignee: Plastics Engineering Company
    Inventors: Gaetano F. D'Alelio, deceased, Phillip A. Waitkus
  • Patent number: 4377673
    Abstract: Novel, unsaturated diacteylene-terminated polyimides and processes for their preparation are disclosed herein. These new polyimides are derivatives of anhydride-terminated aromatic polyimides from which they can be prepared by amidation to provide new unsaturated amide groups having a terminal group containing the structure --C.tbd.C--C.tbd.C--, hereinafter sometimes referred to as "conjugated diynes". These new compositions are more tractable than the original anhydride-terminated polyimides and can be converted at appropriate lower temperatures to crosslinked, insoluble, infusible polymers without by-product formation, thereby extending greatly the applications for which the aromatic polyimides can be employed. Moreover, these new polyimides can undergo the Diels-Alder type of addition with a large number of dienophiles. Certain monomeric materials are also described.
    Type: Grant
    Filed: March 2, 1982
    Date of Patent: March 22, 1983
    Assignee: Plastics Engineering Company
    Inventors: Gaetano F. D'Alelio, deceased, Phillip A. Waitkus
  • Patent number: 4376776
    Abstract: Dibenzofuran derivatives of the formula ##STR1## where R.sup.1, R.sup.2, R.sup.3, X, A, Y, m, n, p and q have the meanings given in the description, and their use for controlling fungi.
    Type: Grant
    Filed: January 26, 1982
    Date of Patent: March 15, 1983
    Assignee: BASF Aktiengesellschaft
    Inventors: Costin Rentzea, Karl-Heinz Feuerherd, Bernd Zeeh, Hubert Sauter, Ernst-Heinrich Pommer
  • 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: RE32761
    Abstract: 3-Arylcarbonyl- and 3-cycloalkylcarbonyl-1-aminoalkyl-1H-indoles, useful as analgesic, anti-rheumatic and anti-inflammatory agents, are prepared by reacting a 3-arylcarbonyl- or 3-cycloalkylcarbonylindole with an aminoalkyl halide in the presence of an acid-acceptor; by reacting a 1-aminoalkyl-1H-indole with an arylcarboxylic acid halide or a cycloalkanecarboxylic acid halide in the presence of a Lewis acid; or by reacting a 3-arylcarbonyl- or 3-cycloalkanecarbonyl-1-tosyloxyalky- or haloalkyl-1H-indole with an amine.
    Type: Grant
    Filed: March 23, 1987
    Date of Patent: October 4, 1988
    Assignee: Sterling Drug Inc.
    Inventor: Malcolm R. Bell