The Oxygen Is In A -coo- Group Patents (Class 544/171)
  • Patent number: 4543353
    Abstract: Esters of 13,14-didehydro prostaglandins have been prepared.
    Type: Grant
    Filed: October 25, 1982
    Date of Patent: September 24, 1985
    Assignee: Farmitalia Carlo Erba S.p.A.
    Inventors: Franco Faustini, Vittoria Villa, Carmelo Gandolfi, Enrico Di Salle
  • Patent number: 4530925
    Abstract: Compounds are described of the formulae (1a) and (1b) ##STR1## in which: --COR.sup.1 is an ester group,n is 1 or 2,W is C.sub.1-7 alkylene,X is cis or trans --CH.dbd.CH or --CH.sub.2 CH.sub.2 --,Y is a saturated heterocyclic amino group,R.sup.2 is substituted or unsubstituted phenylalkyl, thienylalkyl or naphthylalkyl or cinnamyl, andR.sup.3 is --H or C.sub.1-5 alkanoyl, including their salts.These compounds inhibit blood platelet aggregation and bronchoconstriction and may be formulated for use as antithrombotic or antiasthmatic agents.
    Type: Grant
    Filed: March 14, 1984
    Date of Patent: July 23, 1985
    Assignee: Glaxo Group Limited
    Inventors: Eric W. Collington, Peter Hallett, Christopher J. Wallis, John Bradshaw
  • Patent number: 4518799
    Abstract: Novel processes for making arylpropionic acids are described. One process comprises carboxylating particular Grignard compounds which are the products of a catalyzed reaction between corresponding arylmagnesium bromides and ethylene. Furthermore, the reaction making the particular Grignard compounds is itself novel. Also, an improved method is disclosed for making coupled aryl compounds useful as intermediates for making compounds having a pharmaceutical use. For example, particular biaryls may be used to make some of the Grignard compounds herein from which the arylpropionic acids are made. Finally, an improved bromination is disclosed giving high yields of 4-bromo-2-fluoroaniline, which is thereafter coupled with benzene, then used to make the arylmagnesium bromide reacted with ethylene to obtain the particular Grignard compound and subsequent desired arylpropionic acid, i.e. 2-(2-fluoro-4-biphenylyl)propionic acid.
    Type: Grant
    Filed: June 8, 1982
    Date of Patent: May 21, 1985
    Assignee: The Upjohn Company
    Inventor: Thomas A. Hylton
  • Patent number: 4515974
    Abstract: Fumaric acid monoesters can be prepared by introducing a hydroxyl compound at a rate corresponding to the progress of the reaction into a solution or a melt of maleic anhydride, which may optionally be substituted, if appropriate in the presence of a cis-trans catalyst. New fumaric acid monoesters can be formed by the process.
    Type: Grant
    Filed: June 25, 1982
    Date of Patent: May 7, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wilfried Zecher, Rudolf Merten
  • Patent number: 4514396
    Abstract: 13, 14 didehydro-15 cyclic prostacyclins have been prepared.
    Type: Grant
    Filed: September 28, 1983
    Date of Patent: April 30, 1985
    Assignee: Farmitalia Carlo Erba S.p.A.
    Inventors: Nicola Mongelli, Carmelo Gandolfi
  • Patent number: 4495104
    Abstract: A compound of the general formula ##STR1## wherein n is an integer of 10 to 21, inclusive; R is H or lower alkyl having 1 to 4 carbon atoms has pharmaceutical activities such as hypotensive, tissue metabolism stimulating, immuno-regulatory, lysosomal membrane stabilizing and SRS-A production inhibitory activities and is useful as a heart failure remedy, cerebral circulation disturbance remedy, immuno-regulator, and antiallergic drug.
    Type: Grant
    Filed: July 11, 1980
    Date of Patent: January 22, 1985
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Isuke Imada, Tetsuya Okutani, Masazumi Watanabe
  • Patent number: 4495184
    Abstract: A 1-phenyl-3-amino-propane derivative of the formula ##STR1## in which R.sup.1 and R.sup.2 independently represent alkyl radicals or R.sup.1 and R.sup.2 together with the nitrogen atom to which they are bonded complete an optionally substituted heterocyclic radical of the formula ##STR2## and or additionally, if R.sup.4 represents the radical --O--CO--R.sup.5, --O--CO--NHR.sup.6 or --O--SiR.sub.3.sup.7, complete an optionally substituted heterocyclic radical of the formula ##STR3## R.sup.3 represents a hydrogen atom or an alkyl radical, R.sup.4 represents a hydroxyl group, halogen or the radical --O--CO--R.sup.5, --O--CO--NHR.sup.6 or --O--SiR.sub.3.sup.7,R.sup.5 represents an alkyl, alkenyl or halogenoalkyl radical or an optionally substituted aryl or aralkyl radical,R.sup.6 represents an alkyl or alkenyl radical or an optionally substituted aryl radical,R.sup.
    Type: Grant
    Filed: May 23, 1983
    Date of Patent: January 22, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Joachim Knops, Wolfgang Kramer, Paul-Ernst Frohberger
  • Patent number: 4486598
    Abstract: Novel compounds of the following general formula: ##STR1##
    Type: Grant
    Filed: February 22, 1982
    Date of Patent: December 4, 1984
    Assignee: The Upjohn Company
    Inventor: Paul A. Aristoff
  • Patent number: 4482549
    Abstract: Compounds are described of the formula ##STR1## in which --COR.sup.1 is a complex ester or thioester group,W is alkylene,X is cis or trans --CH.dbd.CH or --CH.sub.2 CH.sub.2 --,n is 1 or 2,Y is a saturated heterocyclic amino group having 5-8 ring members, andR.sup.2 is unsubstituted or substituted phenylalkyl, thienzlalkyl, naphthylalkyl or cinnamyl, and their salts and solvates.These compounds inhibit blood platelet aggregation and bronchoconstriction and may be formulated for use as antithrombotic and antiasthmatic agents.
    Type: Grant
    Filed: February 8, 1984
    Date of Patent: November 13, 1984
    Assignee: Glaxo Group Limited
    Inventors: Eric W. Collington, Peter Hallett, Christopher J. Wallis, Norman F. Hayes, John Bradshaw, Malcolm Carter, Alan Wadsworth
  • Patent number: 4468522
    Abstract: Process for the preparation of (omega-carbalkoxy-nor.alkyl) dialkylamines having a linear alkyl chain, comprising the steps of amination of allyl compounds in which at least an allyl carbon atom is a part of a cyclopropane ring which contains one or two carboxyl or carbalkoxy groups on the carbon atom which is adjacent to the allyl carbon, or is a part of a lactone ring, in the presence of catalysts consisting of triarylphosphine complexes of palladium, or trialkyl phosphite complexes of nickel, and the subsequent hydrogenation of the unsaturated amine thus obtained. By so doing, interesting linear amines are obtained, which contain carboxyl units or carbalkoxy units, said amines being useful as additives for the industry of synthetic fibres (viscosity stabilizers for polycaprolactam).
    Type: Grant
    Filed: April 6, 1982
    Date of Patent: August 28, 1984
    Assignee: Anic S.p.A.
    Inventors: Gian Paolo Chiusoli, Mirco Costa, Luciano Pallini, Giuliana Terenghi
  • Patent number: 4447428
    Abstract: Prostanoid compounds are described having the formula: ##STR1## where A is a cyclopentane ring, which is substituted by oxo and/or hydroxy or etherified hydroxy and may be saturated or unsaturated; X is --CH.dbd.CH--or --(CH.sub.2).sub.2 --; R is alkyl having a terminal --COOH or ester group; and Y is amino or substituted amino, particularly heterocyclic amino.The compounds have bronchodilator activity and/or inhibit blood platelet aggregation.The preparation and pharmaceutical formulation of the compounds is also described.
    Type: Grant
    Filed: July 15, 1983
    Date of Patent: May 8, 1984
    Assignee: Glaxo Group Limited
    Inventors: Eric W. Collington, Harry Finch, Roger F. Newton
  • Patent number: 4438112
    Abstract: Prostanoids are described of the formulae ##STR1## (and the salts thereof) in which: X is cis or trans --CH.dbd.CH-- or CH.sub.2 CH.sub.2 --;R.sup.1 is C.sub.1-7 alkyl terminated by --COOR.sup.10 where R.sup.10 is H, C.sub.1-6 alkyl or aralkyl;Y is a saturated heterocyclic amino group; andR.sup.4 is aralkyl (in which the aryl portion is substituted by alkylthio, alkylsulphinyl, alkylsulphonyl, alkanoylamino, aroylamino, phenalkyl, aminosulphonyl, alkanoylaminosulphonyl, phenylsulphonyl, nitro, tetrazolyl, substituted phenyl or thienyl).These compounds inhibit blood platelet aggregation and have bronchodilatory action, and may be formulated for use as anti-asthmatics and antithrombotic agents.
    Type: Grant
    Filed: September 17, 1982
    Date of Patent: March 20, 1984
    Assignee: Glaxo Group Limited
    Inventors: Eric W. Collington, Peter Hallett, Christopher J. Wallis, John Bradshaw
  • Patent number: 4421739
    Abstract: The invention provides compounds which are particularly valuable for use as the active ingredient in sun tan lotions and creams and the like. These compounds have the general formula: ##STR1## in which Y denotes hydrogen or the radical SO.sub.3 H or a salt thereof with an organic or inorganic base, and Z denotes the radical --CH.sub.2 Br or --CHBrBr or a radical Z' which denotes the radical --CH.sub.2 I, --CH.sub.2 R, --CHR'R', --CHO or --COOR", in which R denotes --NR.sub.1 R.sub.2, --N.sup.+ R.sub.1 R.sub.2 R.sub.3, --OR.sub.4, --OCOR.sub.5, --SR.sub.6, --CN, -COOR" or --SSO.sub.3 Na, in which R.sub.1 and R.sub.2 independently denote hydrogen, C.sub.1-18 alkyl or hydroxyalkyl, or R.sub.1 and R.sub.2, together with the nitrogen atom to which they are attached, denote a heterocyclic ring, R.sub.3 denotes C.sub.1-4 alkyl or hydroxyalkyl or sulphonatopropyl, R.sub.4 denotes hydrogen, alkyl, polyoxyethylene, aryl which is optionally substituted, menthyl or dialkylaminoalkyl, R.sub.
    Type: Grant
    Filed: March 14, 1978
    Date of Patent: December 20, 1983
    Assignee: L'Oreal
    Inventors: Claude Bouillon, Charles Vayssie
  • Patent number: 4421927
    Abstract: The present invention relates to a new cinnamoyl-cinnamic acid derivative selected from the group constituted by:(i) the m-cinnamoyl-cinnamic acid derivatives of formula ##STR1## in which: X.sub.o,X.sub.1,X.sub.2,X.sub.3,X.sub.4, which are identical or different, each represent an atom of hydrogen, a halogen, a lower alkyl group, a lower alkoxy group, the group NRR' (where R and R' identical or different, each represent an atom of hydrogen or a lower alkyl group), the group NO.sub.2, CF.sub.3 or OH;R.sub.1 represents an atom of hydrogen or a lower alkyl group;R.sub.2 represents an atom of hydrogen or the methyl group;Y represents a group OH, OR.sub.3 (where R.sub.3 is a lower alkyl group), NRR' (where R and R' are defined as hereinabove) or the group O(CH.sub.2).sub.n NR.sub.4 R.sub.5 (where n is an integer of value 1 to 5--and preferably 2 or 3)--; and R.sub.4 and R.sub.
    Type: Grant
    Filed: October 22, 1981
    Date of Patent: December 20, 1983
    Assignee: Societe de Recherches Industrielles (S.O.R.I.)
    Inventor: Francois Picart
  • Patent number: 4410521
    Abstract: Compounds are described of the formula ##STR1## in which --COR.sup.1 is a complex ester or thioester group,W is alkylene,X is cis or trans --CH.dbd.CH or --CH.sub.2 CH.sub.2 --,n is 1 or 2,Y is a saturated heterocyclic amino group having 5-8 ring members, andR.sup.2 is unsubstituted or substituted phenylalkyl, thienylalkyl, naphthylalkyl or cinnamyl,and their salts and solvates.These compounds inhibit blood platelet aggregation and bronchoconstruction and may be formulated for use as antithrombotic and antiasthmatic agents.
    Type: Grant
    Filed: September 16, 1982
    Date of Patent: October 18, 1983
    Assignee: Glaxo Group Limited
    Inventors: Eric W. Collington, Peter Hallett, Christopher J. Wallis, Norman F. Hayes, John Bradshaw, Malcolm Carter
  • Patent number: 4409213
    Abstract: Prostanoid compounds are described having the formula: ##STR1## where A is a cyclopentane ring, which is substituted by oxo and/or hydroxy or etherified hydroxy and may be saturated or unsaturated; X is --CH.dbd.CH-- or --(CH.sub.2).sub.2 --; R is alkyl having a terminal --COOH or ester group; and Y is amino or substituted amino, particularly heterocyclic amino.The compounds have bronchodilator activity and/or inhibit blood platelet aggregation.The preparation and pharmaceutical formulation of the compounds is also described.
    Type: Grant
    Filed: November 10, 1982
    Date of Patent: October 11, 1983
    Assignee: Glaxo Group Limited
    Inventors: Eric W. Collington, Harry Finch, Roger F. Newton, Christopher J. Wallis
  • Patent number: 4360519
    Abstract: Morpholine derivatives of the formula ##STR1## and their pharmaceutically acceptable acid addition salts[wherein R.sup.1 represents lower alkyl. R.sup.2 represents hydrogen, lower alkyl, benzyl, lower alkoxymethyl or an acyl group; R.sup.3 represents hydrogen, lower alkyl or phenyl; R.sup.4, R.sup.5 and R.sup.6 are independently hydrogen or lower alkyl and R.sup.7 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, aryl(lower)alkyl, tetrahydrofurylmethyl or cycloalkylmethyl] possess analgesic and/or opiate antagonistic activity.
    Type: Grant
    Filed: October 3, 1980
    Date of Patent: November 23, 1982
    Assignee: John Wyeth & Brother Limited
    Inventors: Alan C. White, Edwin T. Edington
  • Patent number: 4342756
    Abstract: Compounds are described of the formula ##STR1## (and their salts and solvates) in which: X is cis or trans --CH.dbd.CH--;R.sup.1 is C.sub.1-7 alkyl terminated by --COOR.sup.3 where R.sup.3 is H, C.sub.1-6 alkyl or C.sub.7-10 aralkyl;Y is a saturated heterocyclic amino group having 5-8 ring members; andR.sup.2 is C.sub.2-4 alkanoyl, C.sub.3-6 alkenyl (optionally substituted), C.sub.1-12 alkyl, or substituted or unsubstituted phenylalkyl, biphenylalkyl or naphthylalkyl.These compounds inhibit blood platelet aggregation and bronchoconstriction and may be formulated for use as antithrombotic and anti-asthmatic agents.
    Type: Grant
    Filed: April 29, 1981
    Date of Patent: August 3, 1982
    Assignee: Glaxo Group Limited
    Inventors: Eric W. Collington, Peter Hallett, Christopher J. Wallis, John Bradshaw, Norman F. Hayes
  • Patent number: 4332961
    Abstract: .alpha.-[4-(4-Trifluoromethylphenoxy)phenoxy]alkanecarboxylic acids (the "4-trifluoromethylphenoxy group" of which may contain one chlorine atom as a substituent) and derivatives thereof useful as a herbicide, a herbicidal composition containing the compound, methods of controlling weeds and production thereof.
    Type: Grant
    Filed: April 15, 1977
    Date of Patent: June 1, 1982
    Assignee: Ishihara Sangyo Kaisha, Ltd.
    Inventors: Ryohei Takahashi, Kanichi Fujikawa, Isao Yokomichi, Sinzo Someya, Nobuyuki Sakashita
  • Patent number: 4327022
    Abstract: Aminoalkylnaphthols and esters thereof, useful as cardiotonic or antibacterial agents, are prepared from the corresponding RO-naphthalenealkylamines, certain of which are also useful as cardiotonic agents.
    Type: Grant
    Filed: August 1, 1979
    Date of Patent: April 27, 1982
    Assignee: Sterling Drug Inc.
    Inventor: Denis M. Bailey
  • Patent number: 4314060
    Abstract: Certain oxaalkanoate zwitterionic surfactant-type compounds and their esters are not only excellent detergents, but also provide superior oral therapy for ulceration of the gastric mucosa. The oxaalkanoate zwitterionic compounds are especially preferred in the management of both gastric and duodenal ulcers.
    Type: Grant
    Filed: July 16, 1979
    Date of Patent: February 2, 1982
    Assignee: The Procter & Gamble Company
    Inventors: James P. Brown, Robert G. Laughlin
  • Patent number: 4306076
    Abstract: The present specification provides novel analogs of carbacyclin (CBA.sub.2), 6a-carba-prostacyclin (6a-carba-PGI.sub.2), which have pronounced prostacyclin-like pharmacological activity, e.g., as platelet anti-aggregatory agents. Specifically the novel chemical analogs of CBA.sub.2 are those substituted by fluoro (C-5), alkyl (C-9), interphenylene (C-5), and methano (C-6a,9). Further provided are benzindene analogs of CBA.sub.2 and substituted forms thereof, i.e., 9-deoxy-2',9-methano (or 2',9-metheno)-3-oxa-4,5,6-trinor-3,7-(1',3'-interphenylene)-PGF.sub.1 compounds. Also provided are a variety of novel chemical intermediates, e.g., substituted bicyclo[3.3.0]octane intermediates, and chemical process utilizing such intermediates which are useful in the preparation of the novel CBA.sub.2 analogs.
    Type: Grant
    Filed: December 22, 1980
    Date of Patent: December 15, 1981
    Assignee: The Upjohn Company
    Inventor: Norman A. Nelson
  • Patent number: 4306075
    Abstract: The present specification provides novel analogs of carbacyclin (CBA.sub.2), 6a-carba-prostacyclin (6a-carba-PGI.sub.2), which have pronounced prostacyclin-like pharmacological activity, e.g., as platelet antiaggregatory agents. Specifically the novel chemical analogs of CBA.sub.2 are those substituted by fluoro (C-5), alkyl (C-9), interphenylene (C-5), and methano (C-6a,9). Further provided are benzindene analogs of CBA.sub.2 and substituted forms thereof, i.e., 9-deoxy-2',9-methano (or 2',9-metheno)-3-oxa-4,5,6-trinor-3,7-(1',3'-interphenylene)-PGF.sub.1 compounds. Also provided are a variety of novel chemical intermediates, e.g., substituted bicyclo[3.3.0]octane intermediates, and chemical process utilizing such intermediates which are useful in the preparation of the novel CBA.sub.2 analogs.
    Type: Grant
    Filed: December 22, 1980
    Date of Patent: December 15, 1981
    Assignee: The Upjohn Company
    Inventor: Paul A. Aristoff
  • Patent number: 4304936
    Abstract: 3-Phenoxy-.alpha.-phenoxy-alkancarboxylic acid derivatives of the formula ##STR1## are disclosed as possessing a surprising selective herbicidal activity. In the formula, Hal is a halogen atom, m is an integer 1, 2 or 3, Y is a hydrogen or halogen atom or the cyano group, Z is a halogen atom or the cyano group, R.sub.1 is hydrogen or C.sub.1 -C.sub.8 alkyl, and R is an acid function. Methods are disclosed for combatting weeds in mono- and dicotyledonous cultures such as cereals, corn, rice, soya and cotton, which comprise applying to the locus to be protected from weeds a dosage of from 0.1 to 10.0 kilograms per hectare of the above compounds.
    Type: Grant
    Filed: October 11, 1979
    Date of Patent: December 8, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Otto Rohr, Georg Pissiotas, Beat Bohner, Kurt Burdeska
  • Patent number: 4285867
    Abstract: Compounds having the formula ##STR1## wherein ##STR2## R.sub.1 is hydrogen, benzyl or alkanoyl, X is C.sub.2-4 alkylene; andZ-W is alkyl, phenylalkyl or pyridylalkyl which can have an oxygen atom as part of the alkyl chain and their use as CNS agents, antidiarrheals and antiemetics. Processes for their preparation and intermediates therefor are described.
    Type: Grant
    Filed: September 19, 1980
    Date of Patent: August 25, 1981
    Assignee: Pfizer Inc.
    Inventors: Michael R. Johnson, Lawrence S. Melvin, Jr.
  • Patent number: 4283533
    Abstract: Amphoteric N-type betaines represented by the formula: ##STR1## wherein: R.sub.f is C.sub.4 -C.sub.20 perfluoroalkyl;R.sup.1 and R.sup.2 are methyl or, together with the N atom to which they are bonded, form a piperidino, morpholino, orN-alkyl(c.sub.1 -C.sub.4)piperazino group; and m is a whole number between 1 and 4 are highly effective in reducing the surface tension of water and of aqueous solutions of inorganic electrolytes, and can be used in environments where non-amphoteric surfactants would fail, e.g. highly acidic oil well applications.
    Type: Grant
    Filed: November 9, 1979
    Date of Patent: August 11, 1981
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: John W. Richter
  • Patent number: 4277471
    Abstract: Biphenylylalkylamines which have anti-arrhythmic activity have been prepared. Pharmaceutical formulations containing such compounds and a method of treating cardiac arrhythmias are provided.
    Type: Grant
    Filed: February 22, 1980
    Date of Patent: July 7, 1981
    Assignee: Eli Lilly and Company
    Inventors: William B. Lacefield, Richard L. Simon
  • Patent number: 4277406
    Abstract: The present invention is concerned with novel triarylmethane dyes possessing in their triaryl structure a 4'-oxo-1'-naphthylidene (or a 4'-oxo-1'-phenylidene) moiety and a phenyl moiety substituted in the ortho-position to the central carbon atom with the group ##STR1## wherein R is alkyl, unsubstituted or substituted with a solubilizing group, and Y is an electron-withdrawing group, which compounds find utility in photographic products and processes.
    Type: Grant
    Filed: December 26, 1979
    Date of Patent: July 7, 1981
    Assignee: Polaroid Corporation
    Inventor: James W. Foley
  • Patent number: 4277407
    Abstract: The present invention is concerned with novel triarylmethane dyes possessing in their triaryl structure a 4'-oxo-1'-naphthylidene (or a 4'-oxo-1'-phenylidene) moiety and a phenyl moiety substituted in the ortho-position to the central carbon atom with the group ##STR1## wherein R is hydrogen; alkyl, unsubstituted or substituted with halo, alkoxy, carboxy-substituted alkoxy, phenoxy or phenyl; or phenyl, unsubstituted or substituted with halo, alkoxy, nitro, dimethylamino or alkyl, which compounds find utility in photographic products and processes.
    Type: Grant
    Filed: December 26, 1979
    Date of Patent: July 7, 1981
    Assignee: Polaroid Corporation
    Inventor: James W. Foley
  • Patent number: 4275201
    Abstract: Aryl substituted diketones and keto-esters, useful as antiviral agents and insecticides, are prepared by reacting an arylalkyl or arylalkenyl iodide with a metal salt of the appropriate diketone or keto-ester.
    Type: Grant
    Filed: February 14, 1979
    Date of Patent: June 23, 1981
    Assignee: Sterling Drug Inc.
    Inventor: Joseph C. Collins
  • Patent number: 4265891
    Abstract: Prostanoid compounds are described having the formula: ##STR1## where A is a cyclopentane ring, which is substituted by oxo and/or hydroxy or etherified hydroxy and may be saturated or unsaturated; X is --CH.dbd.CH-- or --(CH.sub.2).sub.2 --; R is alkyl having a terminal --COOH or ester grup; and Y is amino or substituted amino, particularly heterocyclic amino.The compounds have bronchodilator activity and/or inhibit blood platelet aggregation.The preparation and pharmaceutical formulation of the compounds is also described.
    Type: Grant
    Filed: July 10, 1979
    Date of Patent: May 5, 1981
    Assignee: Glaxo Group Limited
    Inventors: Eric W. Collington, Harry Finch, Roger F. Newton, Christopher J. Wallis
  • Patent number: 4256745
    Abstract: Prostan-1-ol esters and intermediates for their preparation are described; the former compounds exhibit improved organ specificity and a longer duration of activity at lower dosages than the corresponding non-esterified prostaglandins and are useful, inter alia, in triggering abortion, inducing labor and regulating the menstrual cycle.
    Type: Grant
    Filed: March 2, 1978
    Date of Patent: March 17, 1981
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Walter Elger, Olaf Loge, Eckehard Schillinger
  • Patent number: 4252804
    Abstract: Compounds of the formula I ##STR1## wherein m and n are 0, 1 or 2, X represents oxygen, imino, benzylimino, or morpholinoethylimino, Y represents CO, CONH, COO or SO.sub.2, and NR.sub.1 R.sub.2 represents a dimethylamino, diethylamino, dipropylamino, dibutylamino, allylamino, isobutenylamino, cyclopentylamino, cyclohexylamino, cycloheptylamino, cyclooctylamino, N-methyl N-cyclopentylamino, N-methyl N-cyclohexylamino, N-allyl N-cyclohexylamino, adamantylamino, diethoxyethylamino, dimethylaminoethylamino, dimethylaminopropylamino, N-methyl N-dimethylaminopropyl-amino, benzylamino, 3,4,5-trimethoxybenzylamino, phenethylamino, p-chlorophenethylamino, tetrahydrofurfurylamino, tetrahydropyranylmethylamino, pyrrolidino, isoxazolidinyl, piperidino, 4-hydroxypiperidino, 4-m-chlorophenyl-4-hydroxypiperidino, homopiperidino, 1,2,3,6-tetrahydropyridyl, morpholino, 2-methylmorpholino, 2,6-dimethylmorpholino, 2-morpholinoethylamino, thiamorpholino, piperazino, 4-methylpiperazino, 4-(.alpha.
    Type: Grant
    Filed: January 13, 1978
    Date of Patent: February 24, 1981
    Assignee: Metabio-Joullie
    Inventors: Maurice Joullie, Gabriel Maillard, Lucien Lakah, Christian J. M. Warolin
  • Patent number: 4239855
    Abstract: Covers compounds of the formula ##STR1## where R is lower alkyl, lower alkenyl or phenyl and R' and R" are either lower alkyl or form a morpholine ring when taken with the adjacent nitrogen atom. Also covers a method of producing a polyurethane foam and elastomer by utilizing said above compounds as catalysts in reacting an organic polyisocyanate with an organic polyester polyol or polyether polyol in the presence of said catalyst.
    Type: Grant
    Filed: July 21, 1978
    Date of Patent: December 16, 1980
    Assignee: Texaco Development Corp.
    Inventor: Robert L. Zimmerman
  • Patent number: 4235896
    Abstract: Compounds of the formula ##STR1## in which A is lower alkyl, or a substituted or unsubstituted phenyl, thienyl, furyl, indolyl or thiaindolyl radical, R, X.sub.4 and X.sub.5 are hydrogen or lower alkyl, Y is hydrogen, hydroxy, etherified hydroxy, substituted amino, or N-attached heterocyclyl, X.sub.0 is O or OCH.sub.2 CH.sub.2 O, R' represents hydrogen, lower alkyl or acetyl; and acid-addition salts thereof, are novel and useful in pharmacy as hypolipaemiant, hypocholosterolaemiant and cholagogic agents or in the preparation of such agents.
    Type: Grant
    Filed: October 28, 1977
    Date of Patent: November 25, 1980
    Assignee: Orchimed S.A.
    Inventor: Andre Mieville
  • Patent number: 4233298
    Abstract: This invention is concerned with esters of p-carbonylphenoxy-isobutyric acids of the general formulae: ##STR1## wherein R is a phenyl group substituted by one or two halogen atoms;R' is H, CH.sub.3, C.sub.6 H.sub.5, SCH.sub.3, OCH.sub.3, or, SO.sub.2 CH.sub.3 ;R" is CH.sub.3 or C.sub.2 H.sub.5 ;Y is C.sub.1 -C.sub.4 alkoxy, phenoxy, phenoxy substituted by one or two halogen atoms, or, OCH.sub.2 O--CO--C(CH.sub.3).sub.3 ;Z is C.sub.1 -C.sub.4 alkyl, phenyl or R;NR.sub.1 R.sub.2 is N(CH.sub.3).sub.2 N(C.sub.2 H.sub.5).sub.2, morpholino, piperidino, hexamethylenimino, pyrrolidino.This invention is also concerned with acid addition salts obtained from formula Ia compounds with acids.Compounds of formulae I and Ia are useful as hypocholesterolemiant and hypolipidemiant agents.
    Type: Grant
    Filed: September 1, 1977
    Date of Patent: November 11, 1980
    Assignee: Orchimed SA
    Inventor: Andre Mieville
  • Patent number: 4227015
    Abstract: Aryl substituted diketones and keto-esters, useful as antiviral agents and insecticides, are prepared by reacting an arylalkyl or arylalkenyl iodide with a metal salt of the appropriate diketone or keto-ester. The intermediate iodides are prepared by condensing a methyl cyclopropyl ketone with an aromatic aldehyde to give an arylvinyl cyclopropyl ketone, reducing the latter to an arylethyl cyclopropyl carbinol or arylvinyl cyclopropyl carbinol, treating the carbinol with phosphorus tribromide and then with zinc bromide to give an arylalkyl or arylalkenyl bromide, and then replacing the bromine atom by iodine.
    Type: Grant
    Filed: February 14, 1979
    Date of Patent: October 7, 1980
    Assignee: Sterling Drug Inc.
    Inventor: Joseph C. Collins
  • Patent number: 4227009
    Abstract: Phenoxyphenoxy-propionic acid derivatives of the formula ##STR1## exhibit an outstanding herbicidal activity against a wide variety of weed grasses and are well tolerated by dicotyledonous crop plants and various cereals.
    Type: Grant
    Filed: May 24, 1977
    Date of Patent: October 7, 1980
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Manfred Koch, Reinhard Handte, Gerhard Horlein, Heinrich Leditschke, Helmut Kocher, Peter Langeluddeke
  • Patent number: 4223139
    Abstract: Amine salts of tertiary amino acids have been found to be effective as catalysts for polyurethane synthesis and they have been found to exhibit delayed action, in many instances, in the polymerization of urethanes. Typically, the amine salts of tertiary amino acids are formed by initially reacting a primary or secondary amine with an aldehyde and disubstituted acid to form a Mannich adduct and then reacting the resulting Mannich acid adduct with an amine.
    Type: Grant
    Filed: October 23, 1978
    Date of Patent: September 16, 1980
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Ibrahim S. Bechara, Rocco L. Mascioli, Philip J. Zaluska
  • Patent number: 4204062
    Abstract: Amine salts of tertiary amino acids have been found to be effective as catalysts for polyurethane synthesis and they have been found to exhibit delayed action, in many instances, in the polymerization of urethanes. Typically, the amine salts of tertiary amino acids are formed by initially reacting a primary or secondary amine with an aldehyde and disubstituted acid to form a Mannich adduct and then reacting the resulting Mannich acid adduct with an amine.
    Type: Grant
    Filed: October 23, 1978
    Date of Patent: May 20, 1980
    Assignee: Air Products & Chemicals, Inc.
    Inventors: Ibrahim S. Bechara, Rocco L. Mascioli, Philip J. Zaluska
  • Patent number: 4198306
    Abstract: Hydrocarbylpoly(oxyalkylene) aminoesters which are monoesters of a hydrocarbyl-terminated poly(oxyalkylene) alcohol and a monocarboxylic C.sub.2 -C.sub.20 (amino-substituted) alkanoic acid find use as fuel and lubricating oil additives.
    Type: Grant
    Filed: July 3, 1978
    Date of Patent: April 15, 1980
    Assignee: Chevron Research Company
    Inventor: Robert A. Lewis
  • Patent number: 4191765
    Abstract: Compounds of formula I ##STR1## wherein R.sup.1 and R.sup.1' are identical or different and represent hydrogen, an alkyl radical or alkoxy radical having 1-4 carbon atoms, the allyl group, a halogen atom or the nitro group, R.sup.2 represents an acrylic acid radical or an acrylic acid nitrile radical of the formulae ##STR2## wherein R.sup.5 represents hydrogen, an alkyl radical having 1-5 carbon atoms, an aryl radical or aryl-lower alkyl radical either unsubstituted or substituted by lower alkyl or alkoxy, R.sup.6 represents hydrogen or an alkyl radical having 1-8 carbon atoms, R.sup.7 represents hydrogen, a lower alkyl radical or an aryl-lower alkyl radical, R.sup.3 and R.sup.4 represent together with the nitrogen atom a heterocyclic ring with 5-7 members being optionally substituted by C.sub.1 -C.sub.4 alkyl, in which ring one carbon atom may be replaced by one oxygen atom, sulfur atom or one further nitrogen atom, the latter may be substituted, or wherein R.sup.3 represents hydrogen and R.sup.
    Type: Grant
    Filed: August 10, 1978
    Date of Patent: March 4, 1980
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Werner Fritsch, Ulrich Stache, Ernst Lindner
  • Patent number: 4182761
    Abstract: Acyloxy-substituted aryloxyalkyl diketones, useful as anti-viral agents, are prepared either by esterification of the corresponding hydroxy-substituted compounds or by reacting a haloalkyl diketone with an alkali metal salt of an acyloxy-substituted phenol.
    Type: Grant
    Filed: June 7, 1978
    Date of Patent: January 8, 1980
    Assignee: Sterling Drug Inc.
    Inventors: Joseph C. Collins, Guy D. Diana
  • Patent number: 4175947
    Abstract: Phenoxy-phenoxypropionic acid derivatives of the formula ##STR1## wherein R is hydrogen or halogen, and R.sub.1 is substituted alkyl, cyclohexenyl, phenylalkenyl or (substituted) alkinyl, are interesting selective herbicides having a special activity against weed grasses. They are obtained for example by reaction of corresponding phenoxypropionic acid halides with hydroxy compounds of the formula HO--R.sub.1.
    Type: Grant
    Filed: April 21, 1977
    Date of Patent: November 27, 1979
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Manfred Koch, Reinhard Handte, Gerhard Horlein, Hermann Bieringer, Peter Langeluddeke
  • Patent number: 4172945
    Abstract: Compounds are provided having the structure ##STR1## wherein n is 1, 2 or 3, m is 0, 1 or 2, R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 may be the same or different and can be hydrogen, lower alkyl, halo-lower alkyl, acyl, lower alkoxy-carbonyl ##STR2## amido ##STR3## or lower alkoxyalkylene, X is a straight or branched bivalent aliphatic radical and Y is ##STR4## These compounds are useful in the treatment of hypertension.
    Type: Grant
    Filed: July 27, 1978
    Date of Patent: October 30, 1979
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Frederic P. Hauck, Joseph E. Sundeen, Joyce Reid
  • Patent number: 4170653
    Abstract: Disclosed herein are compounds of the formula ##STR1## in which Ar is phenyl or 1-naphthyl; R.sup.1 is hydrogen or lower alkyl; and R.sup.2 and R.sup.3 together with the nitrogen atom to which they are joined form a heterocyclic amine radical selected from the group consisting of 1-pyrrolidinyl, piperidino, morpholino and 4-(lower alkyl)-1-piperazinyl. The compounds are antidepressant agents and methods for their preparation and use also are disclosed.
    Type: Grant
    Filed: September 1, 1977
    Date of Patent: October 9, 1979
    Assignee: Ayerst McKenna and Harrison Limited
    Inventors: Jean-Marie Ferland, Real Laliberte, Wilbur Lippmann, Thomas A. Pugsley
  • Patent number: 4167490
    Abstract: Flexible filters capable of transmitting radiation in the spectral range of 315 to 380 nm and absorbing radiation in the spectral range of 400 to 550 nm consist essentially of a thin flexible film, e.g., polyethylene terephthalate containing or having coated thereon a dye in a concentration of 15 to 60 mg/dm.sup.2 and optionally, as a component of the coating, a thermoplastic organic binder, e.g., cellulose acetate butyrate, present in the coating with the dye, said dye being of the formula: ##STR1## where R.sub.1 is lower alkyl of 1 to 5 carbon atoms; R.sub.2 and R.sub.3, which may be the same or different, are selected from the group consisting of R.sub.1, 2-cyanoethyl, 2-hydroxyethyl and ##STR2## or form a saturated 5- or 6- membered ring; R.sub.4 is taken from the class consisting of lower alkyl of 1 to 5 carbon atoms, aryl or alkaryl of 6 to 9 carbon atoms, and aralkyl.
    Type: Grant
    Filed: December 22, 1975
    Date of Patent: September 11, 1979
    Assignee: E. I. DuPont de Nemours and Company
    Inventor: Catharine E. Looney
  • Patent number: 4160099
    Abstract: Labile quaternary ammonium salts of the following formula (I) and (II) are provided: ##STR1## wherein ##STR2## represents a tertiary aliphatic amine; wherein ##STR3## represents an unsaturated amine; wherein R represents a member selected from the group consisting of a hydrogen atom, a C.sub.1 -C.sub.8 open chain or cyclo alkyl group, a C.sub.1 -C.sub.8 alkoxyalkyl group, a C.sub.1 -C.sub.8 acyloxyalkyl group, a C.sub.1 -C.sub.8 haloalkyl group, a C.sub.1 -C.sub.8 carboxyalkyl group, a C.sub.2 -C.sub.8 alkenylphenyl group, an aryl group, and a substituted aryl group, whose substituents are selected from the group consisting of a halogen atom, an O-lower alkyl (C.sub.1 -C.sub.4) group, an O-acyl group, a nitro group, a carboxyl group, and a carboethoxy group; wherein R.sub.1 which may be the same or different, represents any member defined by R above with the proviso that R.sub.
    Type: Grant
    Filed: September 20, 1976
    Date of Patent: July 3, 1979
    Assignee: Interx Research Corporation
    Inventor: Nicolae S. Bodor
  • Patent number: 4156723
    Abstract: Compounds are provided having the structure ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 or R.sub.4 is hydrogen or acyl, and R.sub.5 is hydrogen or acyl, X is a straight or branched bivalent alkylene radical and Y is ##STR2## These compounds are useful in the treatment of hypertension.
    Type: Grant
    Filed: August 4, 1977
    Date of Patent: May 29, 1979
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Frederic P. Hauck, Michael E. Condon, Joyce Reid
  • Patent number: 4150137
    Abstract: The present invention relates to phenylacetic acid ester derivatives of the following general formula: ##STR1## wherein, R is selected from the group consisting of lower alkyl (other than ethyl) and substituted lower alkyl, and R' may be a hydrogen or methyl.The compounds obtained by the present invention possess a high degree of analgetic ,antipyretic and anti-inflammatory activites and cause little side effects on the gastro-intestinal tracts, when administered orally and topically, and they may be useful as oral and topical analgetics, antipyretics and antiinflammatory agents.
    Type: Grant
    Filed: October 25, 1977
    Date of Patent: April 17, 1979
    Assignee: Hisamitsu Pharmaceutical Co. Inc.
    Inventors: Kanji Noda, Akira Nakagawa, Yuji Ishikura, Hiroyuki Ide