The Carbonyl Is Bonded Directly To Nitrogen Of Morpholine Ring Patents (Class 544/176)
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Patent number: 4493823Abstract: 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: GrantFiled: November 10, 1981Date of Patent: January 15, 1985Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Hinrich Moller, Siegfried Wallat, Friedhelm Bartnik, Wolfgang Pittermann
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Patent number: 4486598Abstract: Novel compounds of the following general formula: ##STR1##Type: GrantFiled: February 22, 1982Date of Patent: December 4, 1984Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4456603Abstract: Polyprenyl carboxylic acid amides of the formula ##STR1## process for their preparation and use thereof for treating liver dysfunction are disclosed.Type: GrantFiled: August 4, 1980Date of Patent: June 26, 1984Assignee: Eisai Co., Ltd.Inventors: Isao Yamatsu, Yuichi Inai, Shinya Abe, Hideaki Watanabe, Toshiji Igarashi, Hiroyuki Shiojiri, Yoshio Tanabe, Kumiko Hara
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Patent number: 4442099Abstract: 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: GrantFiled: November 27, 1981Date of Patent: April 10, 1984Assignee: Research CorporationInventors: Kyriacos C. Nicolaou, Nicos A. Petasis, Steven P. Seitz
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Patent number: 4379928Abstract: Alkyl amides have been synthesized from cyclic anhydrides, carboxyl acids and their esters by contacting them with an amine carbamic acid salt.Type: GrantFiled: March 4, 1981Date of Patent: April 12, 1983Assignee: Union Carbide CorporationInventor: Spyros Theodoropulos
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Patent number: 4349690Abstract: The present invention provides novel 9-deoxy-9-methylene-6-keto-PGE derivatives which are useful for platelet aggregation inhibition and gastric cyctoprotection.Type: GrantFiled: April 23, 1981Date of Patent: September 14, 1982Assignee: The Upjohn CompanyInventor: Gordon L. Bundy
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Patent number: 4334073Abstract: 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: GrantFiled: December 1, 1980Date of Patent: June 8, 1982Assignee: Bayer AktiengesellschaftInventor: Hans-Joachim Diehr
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Patent number: 4326055Abstract: 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: GrantFiled: December 15, 1978Date of Patent: April 20, 1982Assignee: Hoffmann-La Roche Inc.Inventor: Peter Loeliger
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Patent number: 4306076Abstract: 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: GrantFiled: December 22, 1980Date of Patent: December 15, 1981Assignee: The Upjohn CompanyInventor: Norman A. Nelson
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Patent number: 4306075Abstract: 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: GrantFiled: December 22, 1980Date of Patent: December 15, 1981Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4302583Abstract: 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: GrantFiled: April 25, 1979Date of Patent: November 24, 1981Assignee: Bayer AktiengesellschaftInventors: Kurt Findeisen, Karl-Heinz Linker
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Patent number: 4302584Abstract: 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: GrantFiled: August 7, 1980Date of Patent: November 24, 1981Assignee: BASF AktiengesellschaftInventor: Klaus Halbritter
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Patent number: 4291041Abstract: 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: GrantFiled: February 2, 1979Date of Patent: September 22, 1981Assignee: The United States of America as represented by the Secretary of AgricultureInventors: Terrence P. McGovern, Carl E. Schreck
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Patent number: 4263039Abstract: 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: GrantFiled: May 31, 1979Date of Patent: April 21, 1981Assignee: Sumitomo Chemical Company, LimitedInventors: Hiroshi Noguchi, Shunichi Hashimoto, Shigeyoshi Kitamura, Takashi Matsuo, Akihiko Mine, Katsuzo Kamoshita
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Patent number: 4252804Abstract: 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: GrantFiled: January 13, 1978Date of Patent: February 24, 1981Assignee: Metabio-JoullieInventors: Maurice Joullie, Gabriel Maillard, Lucien Lakah, Christian J. M. Warolin
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Patent number: 4249021Abstract: 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: GrantFiled: February 26, 1979Date of Patent: February 3, 1981Assignee: Merck & Co., Inc.Inventors: Edward J. Cragoe, Jr., Haydn W. R. Williams, Otto W. Woltersdorf, Jr.
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Patent number: 4232017Abstract: 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: GrantFiled: May 22, 1979Date of Patent: November 4, 1980Assignee: Gruppo Lepetit S.p.A.Inventors: Giorgio Winters, Nunzio Di Mola
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Patent number: 4226988Abstract: Novel compounds are disclosed having a physiological cooling action on the skin. The compounds are N-substituted p-methane 3-carboxamides.Type: GrantFiled: January 18, 1979Date of Patent: October 7, 1980Assignee: Wilkinson Sword LimitedInventors: Hugh R. Watson, David G. Rowsell, David J. Spring
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Patent number: 4188491Abstract: 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: GrantFiled: March 24, 1978Date of Patent: February 12, 1980Assignee: The Boots Company LimitedInventors: John S. Nicholson, John L. Turner
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Patent number: 4173706Abstract: 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: GrantFiled: April 6, 1978Date of Patent: November 6, 1979Assignee: Institute National de Recherche Chimique AppliqueeInventors: Francois Mathey, Jean Bensoam
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Patent number: 4172146Abstract: 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: GrantFiled: March 15, 1976Date of Patent: October 23, 1979Assignee: Ciba-Geigy CorporationInventor: Friedrich Karrer
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Patent number: 4169108Abstract: 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: GrantFiled: August 16, 1973Date of Patent: September 25, 1979Assignee: Sterling Drug Inc.Inventor: Denis M. Bailey
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Patent number: 4168383Abstract: 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: GrantFiled: June 23, 1978Date of Patent: September 18, 1979Assignee: The Upjohn CompanyInventor: Herman W. Smith
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Patent number: 4168278Abstract: 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: GrantFiled: July 21, 1978Date of Patent: September 18, 1979Assignee: The Dow Chemical CompanyInventor: Harry A. Smith
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Patent number: 4139626Abstract: 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: GrantFiled: January 10, 1977Date of Patent: February 13, 1979Assignee: Syntex (U.S.A.) Inc.Inventor: Colin Beard
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Patent number: 4128712Abstract: 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: GrantFiled: April 7, 1978Date of Patent: December 5, 1978Assignee: The Upjohn CompanyInventor: Gordon L. Bundy
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Patent number: 4115570Abstract: 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: GrantFiled: February 28, 1975Date of Patent: September 19, 1978Assignee: Istituto Chemioterapico Italiano, S.p.A.Inventor: Aldo Garzia
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Patent number: 4105790Abstract: 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: GrantFiled: November 9, 1976Date of Patent: August 8, 1978Assignee: Imperial Chemical Industries LimitedInventors: Clifford R. Hughes, Stephen J. Jackson, John Preston, Peter L. Walton
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Patent number: 4096267Abstract: [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: GrantFiled: June 10, 1975Date of Patent: June 20, 1978Assignee: Merck & Co., Inc.Inventors: Edward J. Cragoe, Jr., Otto W. Woltersdorf, Jr.
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Patent number: 4072710Abstract: 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: GrantFiled: November 7, 1975Date of Patent: February 7, 1978Inventor: Antonio Luis Palomo Coll
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Patent number: 4062841Abstract: 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: GrantFiled: November 23, 1976Date of Patent: December 13, 1977Assignee: The United States of America as represented by the Secretary of AgricultureInventors: Robert R. Mod, James A. Harris, Jett C. Arthur, Jr., Frank C. Magne, Gene Sumrell, Arthur F. Novak