The Carbonyl Is Bonded Directly To Nitrogen Of Morpholine Ring Patents (Class 544/176)
  • Patent number: 4493823
    Abstract: This invention relates to topical cosmetic preparations. More particularly, this invention relates to a topical cosmetic preparation for the treatment of oily hair and seborrheic skin which comprises an effective amount of at least one compound of the formula ##STR1## wherein R.sub.1, R.sub.2, and R.sub.3, any of which may be the same or different, each represent hydrogen, hydroxyl, or --OR.sub.4, where R.sub.4 is an alkyl of from 1 to 6 carbon atoms or a substituted or unsubstituted benzyl, or two of the groups R.sub.1, R.sub.2, and R.sub.3 represent methylenedioxy; X is a substituted or unsubstituted alkylene of from 1 to 3 carbon atoms; and Y is --COOH, --CN, --CONR.sub.5 R.sub.6, or --COOR.sub.7, where R.sub.5 and R.sub.6 each represent hydrogen, alkyl of from 1 to 6 carbon atoms, or substituted or unsubstituted aryl, or aralkyl, or together with the nitrogen atom R.sub.5 and R.sub.6 represent a heterocycle, and R.sub.7 is an alkyl of from 1 to 6 carbon atoms or a substituted or unsubstituted aralkyl.
    Type: Grant
    Filed: November 10, 1981
    Date of Patent: January 15, 1985
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Hinrich Moller, Siegfried Wallat, Friedhelm Bartnik, Wolfgang Pittermann
  • 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: 4456603
    Abstract: Polyprenyl carboxylic acid amides of the formula ##STR1## process for their preparation and use thereof for treating liver dysfunction are disclosed.
    Type: Grant
    Filed: August 4, 1980
    Date of Patent: June 26, 1984
    Assignee: Eisai Co., Ltd.
    Inventors: Isao Yamatsu, Yuichi Inai, Shinya Abe, Hideaki Watanabe, Toshiji Igarashi, Hiroyuki Shiojiri, Yoshio Tanabe, Kumiko Hara
  • Patent number: 4442099
    Abstract: A compound of the formula ##STR1## wherein n is an integer from 2 to 4; m is an integer from 3 to 5; R is OM, OR.sub.1 or NR.sub.2 R.sub.3 where M is a pharmaceutically acceptable cation;R.sub.1, R.sub.2 and R.sub.3 are the same or different and selected from the group consisting of hydrogen, C.sub.1 -C.sub.12 branched, unbranched or cyclic alkyl, aryl and aralkyl; or R.sub.2 and R.sub.3 taken together form a group of the formula ##STR2## can be used as an inhibitor of the lipoxygenase pathway of the arachidonic acid cascade in animals.
    Type: Grant
    Filed: November 27, 1981
    Date of Patent: April 10, 1984
    Assignee: Research Corporation
    Inventors: Kyriacos C. Nicolaou, Nicos A. Petasis, Steven P. Seitz
  • Patent number: 4379928
    Abstract: Alkyl amides have been synthesized from cyclic anhydrides, carboxyl acids and their esters by contacting them with an amine carbamic acid salt.
    Type: Grant
    Filed: March 4, 1981
    Date of Patent: April 12, 1983
    Assignee: Union Carbide Corporation
    Inventor: Spyros Theodoropulos
  • Patent number: 4349690
    Abstract: The present invention provides novel 9-deoxy-9-methylene-6-keto-PGE derivatives which are useful for platelet aggregation inhibition and gastric cyctoprotection.
    Type: Grant
    Filed: April 23, 1981
    Date of Patent: September 14, 1982
    Assignee: The Upjohn Company
    Inventor: Gordon L. Bundy
  • Patent number: 4334073
    Abstract: Process for the preparation of an alpha-hydroxycarboxylic acid amide compound of the formula ##STR1## wherein R.sup.1 is hydrogen or alkyl; andR.sup.2 and R.sup.3 are individually selected from hydrogen, alkyl, alkenyl, alkynyl, aralkyl, cycloalkyl or aryl, each of which may be optionally substituted, or a nitrogen-containing heterocyclic radical; orR.sup.2 and R.sup.3, together with the nitrogen atom to which they are bonded, represent an optionally benzo-fused monocyclic or bicyclic ring, which ring may be substituted and may be partially unsaturated,which process comprises reacting in a first stage an alpha-halocarboxylic acid amide of the formula ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 are identified as above; andHal is chlorine or bromine,with an alkali metal acetate or alkaline earth metal acetate in the presence of a quaternary ammonium salt at a temperature between 20.degree. and 200.degree. C.
    Type: Grant
    Filed: December 1, 1980
    Date of Patent: June 8, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hans-Joachim Diehr
  • Patent number: 4326055
    Abstract: This invention is directed to 5,6,7,8-tetrahydro-naphthyl or indanyl stilbene derivatives which are useful as tumor inhibiting agents, in the treatment of neoplasms, dermatological conditions and rheumatic illnesses.
    Type: Grant
    Filed: December 15, 1978
    Date of Patent: April 20, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Peter Loeliger
  • 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: 4302583
    Abstract: Novel process for the preparation of a monomeric acyl cyanide of the general formula ##STR1## in which R represents optionally substituted alkyl with up to 8 carbon atoms, optionally substituted cycloalkyl with 3 to 12 carbon atoms, optionally substituted aryl or an optionally substituted 5-membered or 6-membered heterocyclic radical, which optionally can be fused with a benzene ring,which process comprises heating the corresponding dimeric acyl cyanide of the general formula ##STR2## in which R has the meaning stated above, to a temperature of from 50.degree. to 300.degree. C. in the presence of a compound having a basic reaction and rapidly removing the monomeric acyl cyanide (I) formed from the reaction mixture.
    Type: Grant
    Filed: April 25, 1979
    Date of Patent: November 24, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Kurt Findeisen, Karl-Heinz Linker
  • Patent number: 4302584
    Abstract: A process for the preparation of 3,3-dimethyl-pent-3-enoic acid amides of the formula I ##STR1## where R.sup.1 and R.sup.2 may be identical or different and each is alkyl of 1 to 4 carbon atoms, or R.sup.1 and R.sup.2 together with the nitrogen on which they are present as substituents form a 5-membered or 6-membered saturated ring which may contain a further hetero-atom,wherein an acetamido-acetal or ketene-acetal-aminal is reacted with 3-methyl-but-2-en-1-ol at from 80.degree. to 220.degree. C., in the presence or absence of an inert organic solvent. The products are valuable intermediates for the preparation of insecticidal cyclopropanecarboxylic acid esters.
    Type: Grant
    Filed: August 7, 1980
    Date of Patent: November 24, 1981
    Assignee: BASF Aktiengesellschaft
    Inventor: Klaus Halbritter
  • Patent number: 4291041
    Abstract: A number of alicyclic carboxamides of the formula ##STR1## wherein n, R.sup.1, R.sup.2, and R.sup.3 are defined hereinbelow have been found to be useful insect repellents.
    Type: Grant
    Filed: February 2, 1979
    Date of Patent: September 22, 1981
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventors: Terrence P. McGovern, Carl E. Schreck
  • Patent number: 4263039
    Abstract: A herbicidal composition which comprises as an active ingredient a m-phenoxybenzamide compound of the formula: ##STR1## wherein X, which may be the same or different, is a halogen atom or a lower alkyl or lower alkoxy group, n is zero or an integer of 1 to 5 and R is a group of the formula: ##STR2## (in which R.sub.1 is a hydrogen atom or a lower alkyl or lower alkenyl group and R.sub.2 is a lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy, lower cycloalkyl, lower haloalkyl, lower alkoxy-substituted lower alkyl, lower cyanoalkyl, lower alkylamino-substituted lower alkyl or benzyl group) or an ethylenimino, pyrrolidino, dimethylpyrrolidino, piperidino, methylpiperidino, hexamethylenimino, morpholino or dimethylmorpholino group.
    Type: Grant
    Filed: May 31, 1979
    Date of Patent: April 21, 1981
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hiroshi Noguchi, Shunichi Hashimoto, Shigeyoshi Kitamura, Takashi Matsuo, Akihiko Mine, Katsuzo Kamoshita
  • 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: 4249021
    Abstract: Substituted 1-oxo-2,2-disubstituted-5-indanacetic acids and their salts, esters and amides are disclosed. The products display a dual pharmaceutical utility in that they exhibit diuretic, saluretic and uricosuric activity.
    Type: Grant
    Filed: February 26, 1979
    Date of Patent: February 3, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Edward J. Cragoe, Jr., Haydn W. R. Williams, Otto W. Woltersdorf, Jr.
  • Patent number: 4232017
    Abstract: New tricyclic ortho-fused heterocyclic compounds of formula ##STR1## wherein A is the group ##STR2## or the group ##STR3## in which R represents hydrogen, (C.sub.1-4)alkyl, phenyl or tolyl and R.sub.1 and may be (C.sub.1-4)alkyl, phenyl or tolyl, R.sub.2 is selected from (C.sub.1-4)alkyl, (C.sub.2-4)alkanoylmethyl, carbo(C.sub.1-3)alkoxymethyl, hydroxy(C.sub.2-4)alkyl, halo(C.sub.2-4)alkyl and a group ##STR4## wherein R.sub.3 is an alkylene group from 2 to 4 carbon atoms and R.sub.4 and R.sub.5 independently represent hydrogen or (C.sub.1-4)alkyl or, taken together with the nitrogen atom, a fully hydrogenated 5 or 6 membered heterocyclic radical which may contain a further heteroatom selected from O, N and S and be optionally substituted by a (C.sub.1-4)alkyl or phenyl group, or R.sub.2 may represent, nil the dotted lines x and y may represent nil or additional bonds; with the proviso that, when the symbol R.sub.
    Type: Grant
    Filed: May 22, 1979
    Date of Patent: November 4, 1980
    Assignee: Gruppo Lepetit S.p.A.
    Inventors: Giorgio Winters, Nunzio Di Mola
  • Patent number: 4226988
    Abstract: Novel compounds are disclosed having a physiological cooling action on the skin. The compounds are N-substituted p-methane 3-carboxamides.
    Type: Grant
    Filed: January 18, 1979
    Date of Patent: October 7, 1980
    Assignee: Wilkinson Sword Limited
    Inventors: Hugh R. Watson, David G. Rowsell, David J. Spring
  • Patent number: 4188491
    Abstract: A process is disclosed for preparing arylpropionic acids of formula Ar--CH(CH.sub.3)--COOH, by reacting an aryl Grignard reagent with a metal pyruvate or with a pyruvamide, to form a hydroxy acid of formula Ar--C(OH)(CH.sub.3)--COOH or its amide, and converting the acid or amide to the product.
    Type: Grant
    Filed: March 24, 1978
    Date of Patent: February 12, 1980
    Assignee: The Boots Company Limited
    Inventors: John S. Nicholson, John L. Turner
  • Patent number: 4173706
    Abstract: A novel process for producing fluorinated organic compounds containing a difluoromethylene group, essentially characterized by reacting organic compounds containing a carbonyl function with molybdenum hexafluoride at room temperature and under atmospheric pressure.
    Type: Grant
    Filed: April 6, 1978
    Date of Patent: November 6, 1979
    Assignee: Institute National de Recherche Chimique Appliquee
    Inventors: Francois Mathey, Jean Bensoam
  • Patent number: 4172146
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 represents cyclohexyl, cyclohexyloxy or the group ##STR2## in which Y represents ##STR3## or the direct bond, Z represents ##STR4## BEING BONDED TO THE PHENYL NUCLEUS, R.sub.2 represents hydrogen, C.sub.1 -C.sub.3 -alkyl, R.sub.3 represents --COOH, (C.sub.1 -C.sub.5 -alkoxy)carbonyl, (C.sub.3 -C.sub.5 -alkenyloxy)carbonyl, (C.sub.3 -C.sub.5 -alkinyloxy)carbonyl, cyclohexyloxycarbonyl, phenoxycarbonyl, (C.sub.3 -C.sub.5 -haloalkenyloxy)carbonyl, the cyano group, a carbamoyl group which is mono- or disubstituted by C.sub.1 -C.sub.5 -alkyl, C.sub.3 -C.sub.5 -alkenyl or C.sub.3 -C.sub.5 -alkinyl, it being possible for the substituents of the carbamoyl group together with the nitrogen atom to which they are bonded to form a saturated 5- or 6-membered heterocyclic ring which can contain in addition an oxygen, a sulphur, or a further nitrogen atom, R.sub.4 represents hydrogen, methyl, or ethyl, R.sub.5 represents C.sub.1 -C.sub.3 -alkyl, formyl, or acetyl, R.sub.
    Type: Grant
    Filed: March 15, 1976
    Date of Patent: October 23, 1979
    Assignee: Ciba-Geigy Corporation
    Inventor: Friedrich Karrer
  • Patent number: 4169108
    Abstract: Aminoalkylnaphthols and esters thereof, useful as cardiotonic agents, prepared from the corresponding RO-naphthalenealkylamines, certain of which are also useful as cardiotonic agents, are disclosed.
    Type: Grant
    Filed: August 16, 1973
    Date of Patent: September 25, 1979
    Assignee: Sterling Drug Inc.
    Inventor: Denis M. Bailey
  • Patent number: 4168383
    Abstract: The present invention provides amides of 6-hydroxy-PGE.sub.1 compounds which are useful pharmacological agents. These analogs are useful as prostacyclin-like drugs.
    Type: Grant
    Filed: June 23, 1978
    Date of Patent: September 18, 1979
    Assignee: The Upjohn Company
    Inventor: Herman W. Smith
  • Patent number: 4168278
    Abstract: One-to-one adducts of primary or secondary amines with .epsilon.-caprolactam are made by heating the reactants in the presence of water at a temperature of between about 170.degree. and 320.degree. C.
    Type: Grant
    Filed: July 21, 1978
    Date of Patent: September 18, 1979
    Assignee: The Dow Chemical Company
    Inventor: Harry A. Smith
  • Patent number: 4139626
    Abstract: Benzene ring substituted benzimidazole-2-carbamate derivatives represented by the formula: ##STR1## where R is a lower alkyl group having 1 to 4 carbon atoms; ##STR2## is a 5, 6, 7 or 8 membered heterocyclic ring containing 1 to 2 hetero atoms; the ##STR3## substitution being at the 5(6)-position; and the pharmaceutically acceptable salts thereof.The compounds are useful as pesticides, particularly as anthelmintic and antifungal agents.
    Type: Grant
    Filed: January 10, 1977
    Date of Patent: February 13, 1979
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Colin Beard
  • Patent number: 4128712
    Abstract: The present invention relates to novel 9-deoxy-9-methylene-PGF.sub.1 -morpholinylamides. These compounds are useful pharmacological agents, and are useful for the same purposes as the corresponding 9-deoxy-9-methylene-PGF-type acids.
    Type: Grant
    Filed: April 7, 1978
    Date of Patent: December 5, 1978
    Assignee: The Upjohn Company
    Inventor: Gordon L. Bundy
  • Patent number: 4115570
    Abstract: Compounds of the formula ##STR1## wherein A is alkylene, R.sub.1, R.sub.2, and R.sub.3 are hydrogen or lower alkoxy, and R.sub.4 is ##STR2## in which R.sub.5 and R.sub.6 are hydrogen or lower alkyl, with the proviso that at least one of R.sub.5 and R.sub.6 is lower alkyl, and >X is oxygen, ##STR3## or >N--R.sub.7 wherein R.sub.7 and R.sub.8 are hydrogen or lower alkyl, depress the activity of the central nervous system when administered to a living animal.
    Type: Grant
    Filed: February 28, 1975
    Date of Patent: September 19, 1978
    Assignee: Istituto Chemioterapico Italiano, S.p.A.
    Inventor: Aldo Garzia
  • Patent number: 4105790
    Abstract: The invention concerns .alpha.-aminoacyl derivatives of phenyl-, phenoxy-, thiophenoxy- and phenylsulphinylalkanoic acids together with their amides, esters and pharmaceutically acceptable salts; processes for their preparation; and pharmaceutical compositions for therapeutic use in inhibiting the formation of thrombi and also in reducing the persistence of thrombi formed in the blood of warm blooded animals. Representative compounds of the invention are methyl 4-(aminoacetyl)phenoxyacetate, 4-(aminoacetyl)phenoxyacetic acid and methyl 4-(aminoacetyl)-thiophenoxyacetate, preferably as their hydrochlorides.
    Type: Grant
    Filed: November 9, 1976
    Date of Patent: August 8, 1978
    Assignee: Imperial Chemical Industries Limited
    Inventors: Clifford R. Hughes, Stephen J. Jackson, John Preston, Peter L. Walton
  • Patent number: 4096267
    Abstract: [1-Oxo-2-aryl or thienyl-2-substituted-5-indanyloxy (or thio)]aklanoic acid, derivatives thereof, their salts, esters and amides are disclosed. The products display a dual pharmaceutical utility in that they exhibit diuretic, saluretic and uricosuric activity. Also disclosed are processes for the preparation of such [1-oxo-2-aryl or thienyl-2-substituted-5-indanyloxy (or thio)]alkanoic acids, pharmaceutical compositions comprising therapeutically effective amounts of such compounds and methods of treatment comprising administering such compounds and compositions.
    Type: Grant
    Filed: June 10, 1975
    Date of Patent: June 20, 1978
    Assignee: Merck & Co., Inc.
    Inventors: Edward J. Cragoe, Jr., Otto W. Woltersdorf, Jr.
  • Patent number: 4072710
    Abstract: A process for preparing acid chlorides, wherein a silyl ester having an aliphatic, aromatic, alkanoaromatic or heterocyclic group which may support substituents, and having a low molecular weight alkyl or phenyl group is reacted with thionyl chloride in an inert solvent at a temperature of from -15.degree. to 50.degree. C, preferably from 10.degree. to 50.degree. C.
    Type: Grant
    Filed: November 7, 1975
    Date of Patent: February 7, 1978
    Inventor: Antonio Luis Palomo Coll
  • Patent number: 4062841
    Abstract: Acetylthio amides and esters were prepared by the free radical addition of thiolacetic acid to the terminal and nonterminal double bonds of N-substituted fatty amides and fatty esters. The free radical additions of the thiolacetic acid to the unsaturated compounds were initiated by irradiation using cobalt-60. The process using irradiation with cobalt-60 was also used to bring about the addition of bromotrichloromethane to N-substituted fatty amides and fatty esters to produce halogen-containing amides and esters. These new sulfur or halogen-containing compounds were found to have antimicrobial activity and to possess properties making them useful as antimicrobial agents.
    Type: Grant
    Filed: November 23, 1976
    Date of Patent: December 13, 1977
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventors: Robert R. Mod, James A. Harris, Jett C. Arthur, Jr., Frank C. Magne, Gene Sumrell, Arthur F. Novak