Five-membered Ring In Substituent Q Patents (Class 564/189)
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Patent number: 4931591Abstract: Compounds of the formula ##STR1## in which R.sub.1 represents hydrogen or acyl, A represents an optionally N-alkylated .alpha.-amino acid residue which is bonded N-terminally to R.sub.1 and C-terminally to the group --NR.sub.2 --, R.sub.2 represents hydrogen or lower alkyl, R.sub.3 represents hydrogen, lower alkyl, optionally etherified or esterified hydroxy-lower alkyl, cycloalkyl, cycloalkyl-lower alkyl, bicycloalkyl-lower alkyl, tricycloalkyl-lower alkyl, aryl or aryl-lower alkyl, R.sub.4 represents hydroxy or etherified or esterified hydroxy, R.sub.5 represents lower alkyl having 2 or more carbon atoms, optionally etherified or esterified hydroxy-lower alkyl, cycloalkyl, cycloalkyl-lower alkyl, bicycloalkyl, bicycloalkyl-lower alkyl, tricycloalkyl, tricycloalkyl-lower alkyl, aryl, aryl-lower alkyl, optionally substituted carbamoyl, optionally substituted amino, optionally substituted hydroxy or optionally substituted mercapto and R.sub.Type: GrantFiled: July 12, 1989Date of Patent: June 5, 1990Assignee: Ciba-Geigy CorporationInventors: Peter Buhlmayer, Vittorio Rasetti, Walter Fuhrer, James L. Stanton, Richard Goschl
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Patent number: 4898977Abstract: The invention relates to novel processes and intermediates for the preparation of 5-amino-4-hydroxyvaleric acid derivatives of the formula ##STR1## in which R.sup.1 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl or the radical of a natural amino acid, R.sup.2 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl, amino, hydroxy, mercapto, sulphinyl, sulphonyl or the radical of a natural amino acid, and R.sup.3 represents optionally substituted hydroxy or amino, by sigmatropic rearrangement of a suitable allyl ester, halolactonisation of the resulting .gamma.,.delta.-unsaturated acid or of a suitable derivative thereof, exchange of halogen for a nitrogen-containing nucleophile, opening of the lactone ring and freeing of the amino group. Compounds of the formula I are starting materials for the preparation of renin-inhibitors which have an anti-hypertensive action.Type: GrantFiled: August 13, 1987Date of Patent: February 6, 1990Assignee: Ciba-Geigy CorporationInventors: Peter Herold, Christof Angst
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Patent number: 4888353Abstract: Carboxamides represented by the formula (I): ##STR1## wherein Z represents the carbon atoms necessary to complete a 5- to 7-membered ring,R.sup.1, R.sup.2, and R.sup.3 may be the same or different and are selected from the group consisting of a hydrogen atom, a lower alkyl group, a cycloalkyl group, a halogen atom, an amino group, a lower alkylamino group, an alkoxy group, an acylamido group, a sulfonamido group, and a nitro group; andA represents an aminoalkyl moiety and acid addition salts thereof.Type: GrantFiled: May 23, 1986Date of Patent: December 19, 1989Assignee: Erbamont, Inc.Inventors: Daniel Lednicer, Jung-Hui Sun
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Patent number: 4872902Abstract: The invention relates to the novel cyclohexanediones of formula I ##STR1## in which R is hydrogen or C.sub.1 -C.sub.6 -alkyl,A is R.sub.2, OR.sub.3 or NR.sub.3 R.sub.4,R.sub.2 is C.sub.1 -C.sub.6 -alkyl that is unsubstituted or is mono-substituted by C.sub.1 -C.sub.4 -alkoxy or mono- or poly-substituted by halogen, or is C.sub.3 -C.sub.6 -cycloalkyl,R.sub.3 is C.sub.1 -C.sub.6 -alkyl or C.sub.3 -C.sub.6 -cycloalkyl, or is phenyl or benzyl each of which is unsubstituted or is mono-, di- or tri-substituted by R.sub.5,R.sub.4 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.3 -C.sub.6 -cycloalkyl,R.sub.3 and R.sub.4 are, in addition, together with the nitrogen atom to which they are bonded, a pyrrolidine, morpholine or piperidine radical,B is one of the radicals ##STR2## m is 0, 1, 2 or 3, R.sub.5 is halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkylsulphinyl or C.sub.1 -C.sub.Type: GrantFiled: February 8, 1988Date of Patent: October 10, 1989Assignee: Ciba-Geigy CorporationInventor: Hans-Georg Brunner
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Patent number: 4870104Abstract: 11-Haloprostane derivatives of general formula I ##STR1## wherein X is F, Cl or Br,R.sub.1 is the residue CH.sub.2 OH or ##STR2## wherein R.sub.2 means a hydrogen atom, an alkyl, cycloalkyl, aryl, phenacyl or heterocyclic residue,A is a --CH.sub.2 --CH.sub.2 -- or cis-CH.dbd.CH-group,B is a --CH.sub.2 --CH.sub.2 -- or trans-CH.dbd.CH-- or a --C.tbd.C-group,W is an ethylenedioxymethylene group or a hydroxymethylene group,D and E together mean a direct bond orD is a C.sub.1-10 -alkylene group,E is an oxygen or sulfur atom, a direct bond, a --C.tbd.C-bond or a --CR.sub.6 .dbd.CR.sub.7 -group with R.sub.6 and R.sub.7 meaning a hydrogen atom, a chlorine atom or an alkyl group,R.sub.4 is a hydroxy group,R.sub.5 is a hydrogen atom, an alkyl, a cycloalkyl, an aryl or a heterocyclic group, andthe salts thereof with physiologically compatible bases, processes for their preparation, and use thereof as agents inhibiting gastric acid secretion.Type: GrantFiled: November 12, 1986Date of Patent: September 26, 1989Assignee: Schering AktiengesellschaftInventors: Helmut Vorbruggen, Norbert Schwarz, Olaf Loge, Claus-Steffen Sturzebecher, Walter Elger
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Patent number: 4859706Abstract: Carboxamides of the general formula I ##STR1## where R.sup.1 is C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.3 -C.sub.10 -cycloalkyl, C.sub.3 -C.sub.10 -cycloalkyenyl or C.sub.4 -C.sub.10 -cycloalkenylalkyl, and R.sup.2 and R.sup.3 are each hydrogen, halogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.3 -haloalkyl. C.sub.1 -C.sub.3 -haloalkoxy or methylthio, and their use for combating pests.Type: GrantFiled: August 6, 1987Date of Patent: August 22, 1989Assignee: BASF AktiengesellschaftInventors: Rainer Buerstinghaus, Peter Hofmeister, Christoph Kuenast
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Patent number: 4851541Abstract: A process for preparing a 4,5-tri or tetramethylene-4-isothiazoline-3-one comprises cyclizing a 2-alkyl or aralkyl thio-1-cycloalkene-1-carboxamide in the form of its sulfoxide in an organic solvent in the presence of a acid chloride and adding to the resulting 4,5-tri or tetramethylene-4-isothiazoline-3-one hydrochloride a mineral or organic base or water so as to free the 4,5-tri or tetramethylene-4-isothiazoline-3-one in the form of a free base.Type: GrantFiled: June 5, 1986Date of Patent: July 25, 1989Assignee: Centre International de Recherches Dermatologiques (C.I.R.D.)Inventors: Jean Maignan, Serge Restle, Michel Colin
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Patent number: 4837342Abstract: A prostacyclin analogue having the formula: ##STR1## wherein R.sup.1 is --CO.sub.2 R.sup.5 (wherein R.sup.5 is a hydrogen atom, a straight chain or branched alkyl group having from 1 to 12 carbon atoms, an aralkyl group having from 7 to 12 carbon atoms, a cycloalkyl group having from 4 to 7 carbon atoms and unsubstituted or substituted by at least one alkyl group having from 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, or one equivalent of a cation), or --CONR.sup.6 R.sup.7 (wherein each of R.sup.6 and R.sup.7 is a hydrogen atom or an alkyl group having from 1 to 10 carbon atoms, or R.sup.6 and R.sup.7 together with the adjacent nitrogen atom, form a 5- or 6-membered substituted or unsubstituted hetero ring which may contain a hetero atom other than said nitrogen atom); A is --CH.sub.2 CH.sub.2 CH.sub.2 --, CH.sub.2 --O--CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --O--CH.sub.2 -- or --CH.dbd.CHCH.sub.2 CH.sub. 2 --; B is trans --CH.dbd.CH-- or --C.Type: GrantFiled: February 13, 1987Date of Patent: June 6, 1989Assignees: Sagami Chemical Research Center, Toa Eiyo Ltd.Inventors: Masakatsu Shibasaki, Atsuo Takahashi, Tuyoshi Aoki, Kentaro Kogi, Yozo Nishimiya, Takeshi Nara, Takashi Yamaguchi
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Patent number: 4827033Abstract: A naphthenic acid amide having the formula: ##STR1## where R is the hydrocarbon portion of a naphthenic acid,R.sub.1 is H or MeX is O or NH, andn is a number having the value of 1-10.The method of producing such amides is also disclosed.Type: GrantFiled: May 18, 1987Date of Patent: May 2, 1989Assignee: Nalco Chemical CompanyInventors: Sam Ferguson, Darrell D. Reese
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Patent number: 4783480Abstract: A 6-keto-prostaglandin E.sub.1 derivative of the formula: ##STR1## (wherein R.sup.1 represents an amino acid or amino alcohol residue, R.sup.2 represents a single bond or an alkylene group of from 1 to 4 carbon atoms, R.sup.3 represents (i) an alkyl group of from 1 to 8 carbon atoms, (ii) a cycloalkyl group of from 4 to 7 carbon atoms, which may be unsubstituted or substituted by at least one alkyl group of from 1 to 8 carbon atoms or (iii) a phenyl or phenoxy group, which may be unsubstituted or substituted by chlorine, trifluoromethyl or alkyl of from 1 to 3 carbon atoms, provided that when R.sup.2 represents a single bond R.sup.3 does not represent phenoxy)cyclodextrin clathrates thereof and non-toxic salts thereof possess selective cytoprotective activity.Type: GrantFiled: January 28, 1987Date of Patent: November 8, 1988Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Hirohisa Wakatsuka, Tadao Okegawa, Yoshinobu Arai
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Patent number: 4762949Abstract: Synthetically produced substantially pure biologically active compounds having the general formula ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.20 alkyl, alkenyl, aryl, aralkyl, cycloalkyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkenyl, alkylcycloalkenyl, or cycloalkenylalkyl;R.sub.2 is hydrogen, C.sub.1 -C.sub.10 alkyl or an amide-substituted alkyl having up to 10 carbon atoms;R.sub.3 is a cyclic, straight or branched chain hydrocarbon group having 2-12 carbon atoms, particularly --(CH.sub.2).sub.n --, wherein n is 2-12; orR.sub.2 and R.sub.3 are linked together to form an alkylene chain; andR.sub.4 is selected from ##STR2## (substituted or unsubstituted carbamimidoyl), ##STR3## (dimethylpyrimidyl), or ##STR4## (carbamyl) wherein each of R.sub.5, R.sub.6, and R.sub.7 is hydrogen or the same or different C.sub.1 -C.sub.8 alkyl group. The compounds are useful as bactericides for a wide variety of bacteria, including S.pyogenes, B.subtilis, K.pneumoniae, M.avium, B.fragilis, C.perfringens and C.albicans.Type: GrantFiled: January 24, 1983Date of Patent: August 9, 1988Assignee: University of Illinois FoundationInventors: Kenneth L. Rinehart, Jr., Guy T. Carter, Michael T. Cheng
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Patent number: 4760179Abstract: Substituted aminoxy propionamide derivatives corrsponding to the formula ##STR1## said derivatives being useful as color improvers and stabilizers in various polymeric substrates.Type: GrantFiled: April 4, 1986Date of Patent: July 26, 1988Assignee: Ciba-Geigy CorporationInventor: Ramanathan Ravichandran
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Patent number: 4752615Abstract: A compound of the formula: ##STR1## useful as a fungicidal agent against phytopathogenic fungi, particularly their strains resistant to benzimidazole, thiophanate and/or cyclic imide fungicides.Type: GrantFiled: November 13, 1986Date of Patent: June 21, 1988Assignee: Sumitomo Chemical Company, LimitedInventors: Junya Takahashi, Toshiro Kato, Hiroshi Noguchi, Yukio Oguri, Shigeo Yamamoto, Katsuzo Kamoshita
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Patent number: 4716241Abstract: Novel cyclopentane derivatives which are useful as an intermediate for the preparation of N-(L-aspartyl)-N'-(2,2,5,5-tetramethylcyclopentanecarbonyl)-R-1,1-diaminoe thane are represented by the formula (I) ##STR1## wherein R.sub.1 is hydrogen and R.sub.2 is cyano, formyl, carbamoyl, alkanesulfonyloxy, or ##STR2## wherein R.sub.3 and R.sub.4 are the same or different and represent alkyl, substituted alkyl or R.sub.1 and R.sub.2 are combined to be methylsulfinylmethylene, acetoxymethylthiomethylene, halomethylthiomethylene, methylthiomethylene, alkoxy-methylene, or --CH.sub.2 --O--.Type: GrantFiled: February 28, 1986Date of Patent: December 29, 1987Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Takayoshi Yamauchi, Kaneaki Hattori, Shunichi Ikeda, Kentaro Tamaki
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Patent number: 4716175Abstract: Certain substituted amides of saturated fatty acids are potent inhibitors of the enzyme acyl-CoA:cholesterol acyltransferase and are thus useful agents for inhibiting the intestinal absorption of cholesterol.Type: GrantFiled: February 24, 1987Date of Patent: December 29, 1987Assignee: Warner-Lambert CompanyInventors: Milton L. Hoefle, Ann Holmes, Bruce D. Roth
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Patent number: 4708959Abstract: A 4,5-trimethylene-4-isothiazoline-3-one of the formula ##STR1## wherein R.sub.1 represents (i) hydrogen, (ii) alkyl having 1-12 carbon atoms, (iii) alkyl having 2 or 3 carbon atoms and substituted by one or two hydroxy groups, (iv) alkenyl having 3 to 6 carbon atoms, (v) ##STR2## wherein n is 0 or 1, m is 1 or 2, R.sup.1 is hydrogen or lower alkyl having from 1 to 5 carbon atoms and R.sub.2 is hydrogen, lower alkyl, nitro, trifluoromethyl or halogen, (vi) cycloalkyl having 3 to 6 carbon atoms and (vii) ##STR3## wherein R.sub.3 is hydrogen, alkyl having 1-12 carbon atoms or ##STR4## defined above, or the salt thereof with a mineral or organic acid. These compounds are useful as bactericides or fungicides.Type: GrantFiled: July 27, 1983Date of Patent: November 24, 1987Assignee: Centre International de Recherches Dermatologiques (C.I.R.D.)Inventors: Braham Shroot, Jean Maignan
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Patent number: 4701553Abstract: Unsaturated cyclic keto acid may be prepared by cyclizing alken-2-yl dicarboxylic acid anhydride with Lewis acid catalyst in anhydrous Friedel-Craft solvent. Amides of these unsaturated cyclic keto acids useful as friction improvers in lubricating oils, may be prepared by reaction of an amine such as ethanolamine with an unsaturated cyclic keto acid.Type: GrantFiled: January 28, 1983Date of Patent: October 20, 1987Assignee: Texaco Inc., WhiteInventor: Justin C. Powell
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Patent number: 4692553Abstract: Cyclohexenone derivatives of the formula ##STR1## where R.sup.1 is hydrogen, methoxycarbonyl, ethoxycarbonyl, methyl or cyano, R.sup.2 is alkyl, R.sup.3 is alkyl, alkenyl, haloalkenyl, or propargyl, R.sup.4 is hydrogen or alkyl, R.sup.5 is hydrogen, alkyl, acyl, formyl, cycloalkylcarbonyl, methoxyalkylcarbonyl, unsubstituted or substituted benzoyl, alkoxycarbonyl, benzyloxycarbonyl, phenoxycarbonyl, alkylthiocarbonyl, N,N-dialkylcarbamyl, N-alkylcarbamyl, N-cycloalkylcarbamyl, N-alkoxy-N-alkylcarbamyl, unsubstituted or substituted N-phenylcarbamyl, alkylsulfonyl, alkenylsulfonyl, haloalkylsulfonyl, N-alkylsulfamyl, N,N-dialkylsulfamyl, N-acyl-N-alkylsulfamyl, N-alkyl-N-methoxycarbonylsulfamyl, dialkoxyphosphoryl, dialkoxythiophosphoryl, 2-haloalkanoyl, acyloxyacetyl or alkoxyoxalyl, and R.sup.6 is alkyl, halogen, hydroxyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro or amino, and salts of these compounds, and the use of these compounds for controlling unwanted plant growth.Type: GrantFiled: July 26, 1985Date of Patent: September 8, 1987Assignee: BASF AktiengesellschaftInventors: Michael Keil, Ulrich Schirmer, Dieter Jahn, Rainer Becker, Bruno Wuerzer, Norbert Meyer
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Patent number: 4622410Abstract: The present invention relates to intermediates of the general formula: ##STR1## (wherein Y and Z, which may be the same or different, each represents a trans-vinylene group or an ethylene group, R.sup.2 represents a hydrogen atom or a methyl or ethyl group, R.sup.3 represents a single bond or an alkylene group of 1 to 5 carbon atoms, R.sup.4 represents an alkyl group of 1 to 8 carbon atoms, a cycloalkyl group of 4 to 7 carbon atoms unsubstituted or substituted by at least one alkyl group of 1 to 8 carbon atoms or a phenyl or phenoxy group unsubstituted or substituted by at least one halogen atom, trifluoromethyl group or alkyl group of 1 to 4 carbon atoms, R.sup.5 represents a hydroxy- protecting group which can be removed in acidic conditions and W.sup.1 represents a group of the formula: --COOR.sup.1, --CON(R.sup.6).sub.2, --CH.sub.2 OR.sup.5 or --CH(OR.sup.7)CH.sub.2 OR.sup.5 (in which R.sup.1 represents a hydrogen atom or an alkyl group of 1 to 12 carbon atoms, the groups R.sup.Type: GrantFiled: March 18, 1985Date of Patent: November 11, 1986Assignee: Ono Pharmaceutical Co. Ltd.Inventors: Nobuyuki Hamanaka, Hideo Takada, Yoshinobu Arai
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Patent number: 4618687Abstract: A cyclopentenone compound represented by the following formula: ##STR1## has an antitumor effect and can be produced from the antibiotic XK-213.Type: GrantFiled: April 18, 1985Date of Patent: October 21, 1986Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Tadashi Hirata, Hiromitsu Saito, Makoto Morimoto
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Patent number: 4569689Abstract: Aniline derivatives of the formula ##STR1## where R.sup.1 is alkoxy, alkylthio, unsubstituted or substituted cycloalkoxy or the radical --NR.sup.2 R.sup.3, X is --CH.sub.2 --, --CH(OH)-- or --CO--, A is an unsubstituted or substituted alkylene chain, B is unsubstituted or substituted methylene or dimethylene, Z is hydrogen, halogen, alkyl, alkoxy, haloalkyl or haloalkoxy, and n is 1, 2 or 3, are used for controlling undesirable plant growth.Type: GrantFiled: June 14, 1984Date of Patent: February 11, 1986Assignee: BASF AktiengesellschaftInventors: Ulrich Schirmer, Norbert Goetz, Bruno Wuerzer
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Patent number: 4570014Abstract: Novel plant growth regulant composition comprising as an active ingredient at least one cycloalkanecarboxylic acid compound of the formula ##STR1## in which R is hydroxyl, alkoxy, aralkoxy, amino, alkylamino, dialkylamino or the radicalO.sup..crclbar. M.sup..sym.whereinM.sup..sym. is one alkali metal ion equivalent or alkaline earth metal ion equivalent, or an ammonium, alkylammonium, dialkylammonium, trialkylammonium or tetraalkylammonium ion,R.sup.1 is amino or the radical ##STR2## wherein R.sup.2 is hydrogen, alkyl or aryl, orR.sup.1 is the radical --N.sup..sym. H.sub.3 X.sup..crclbar.,wherein X.sup.63 is chloride, bromide or iodide, and n is 1, 2, 3, 4 or 5,in admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent.Type: GrantFiled: December 15, 1981Date of Patent: February 11, 1986Assignee: Bayer AktiengesellschaftInventors: Rolf Schroder, Klaus Lurssen
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Patent number: 4566900Abstract: Aniline derivatives of the formula ##STR1## where R.sup.1, Y, A, Z and n have the meanings given in the description, are used for controlling undesirable plant growth.Type: GrantFiled: December 1, 1982Date of Patent: January 28, 1986Assignee: BASF AktiengesellschaftInventors: Peter Plath, Ulrich Schirmer, Gernot Reissenweber, Bruno Wuerzer, Guenter Retzlaff
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Patent number: 4560786Abstract: .DELTA..sup.8,9 -Prostane derivatives of Formula I ##STR1## wherein R.sub.1 is CH.sub.2 OH or ##STR2## wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, or a heterocyclic residue; or R.sub.1 is ##STR3## wherein R.sub.3 is an acid residue or R.sub.2 ; A is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH;B is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH-- or --C.tbd.C--W is a free or functionally modified hydroxymethylene group or free or functionally modified ##STR4## wherein the OH--group can be in the .alpha.-- or .beta.-- position; D and E jointly are a direct bond orD is straight chain or branched alkylene or alkenylene of 1-10 carbon atoms which can optionally be substituted by fluorine atoms, and E is oxygen, sulfur, a direct bond, --C.tbd.C-- or --CR.sub.6 .dbd.CR.sub.7 --, wherein R.sub.6 and R.sub.7 differ from each other and each is hydrogen, chlorine or alkyl;R.sub.4 is free or functionally modified hydroxy andR.sub.Type: GrantFiled: June 24, 1982Date of Patent: December 24, 1985Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Norbert Schwarz, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Michael-Harold Town
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Patent number: 4552875Abstract: Carbacyclinamides of Formula I ##STR1## wherein R.sub.1 is NHR.sub.4, wherein R.sub.4 is H, --(CH.sub.2).sub.n --R.sub.8 or straight-chained or branched aliphatic groups of 1-10 carbon atoms, cycloalkyl of 3-10 carbon atoms, aryl, or lower mono- or polyhydroxyalkyl of 2-8 carbon atoms, or R.sub.1 is NR.sub.4 R.sub.5 wherein R.sub.4 and R.sub.5 each are straight-chained or branched, lower, mono- or polyhydroxyalkyl of 2-8 carbon atoms, or R.sub.4 and R.sub.5 together with the adjoining N-atom form a 5- or 6-membered heterocycle which can optionally contain additional hetero atoms and can be substituted; or R.sub.1 is NR.sub.4 R.sub.5 wherein R.sub.4 is an aliphatic group of 1-10 carbon atoms, cycloalkyl of 3-10 carbon atoms, and R.sub.5 is straight-chained or branched aliphatic group of 1-10 carbon atoms, cycloalkyl of 3-10 carbon atoms, aryl, or lower, mono- or polyhydroxyalkyl of 2-8 carbon atoms;n is 1-4;R.sub.8 is --CONH.sub.2 or --N(C.sub.1 -C.sub.4 -alkyl).sub.2 ;R.sub.Type: GrantFiled: July 1, 1983Date of Patent: November 12, 1985Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Gerda Mannesmann, Bob Nieuweboer, Michael H. Town
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Patent number: 4539421Abstract: The title compounds correspond to the formula ##STR1## and are useful as stabilizers for organic polymers and lubricating oils to counteract the degradative effects of heat, light and air.Type: GrantFiled: October 11, 1983Date of Patent: September 3, 1985Assignee: Ciba-Geigy CorporationInventors: John D. Spivack, Stephen D. Pastor, Paul Odorisio
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Patent number: 4536598Abstract: A new color-forming 4-(4'-secondary or tertiary-amino)anilino-1-carboxamidonaphthalene dye precursor in a photographic material and process enables formation of a dye image by means of cross-oxidation without the need for a coupling reaction. The color-forming 4-(4'-secondary or tertiary-amino)anilino-1-carboxamidonaphthalene dye precursor is useful in a photographic silver halide material for producing (i) a dye image, or (ii) a dye image and silver image. The exposed photographic material is processed to produce (a) a positive dye image, (b) a negative dye and negative silver image, (c) a negative dye image or (d) a positive dye image and a positive silver image. New naphthoquinoneimide dyes are also described.Type: GrantFiled: March 10, 1983Date of Patent: August 20, 1985Assignee: Eastman Kodak CompanyInventors: James E. Klijanowicz, Csaba A. Kovacs
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Patent number: 4495077Abstract: Amides of unsaturated cyclic keto acids, useful as friction improvers in lubricating oils, may be prepared by reaction of an amine such as ethanolamine with an unsaturated cyclic keto acid.Type: GrantFiled: January 28, 1983Date of Patent: January 22, 1985Assignee: Texaco Inc.Inventors: Justin C. Powell, Stephen A. Levine
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Patent number: 4493844Abstract: 2,2'-Bridged[1,1'-biphenyl]-3-ylmethyl carboxamides and insecticidal compositions containing these carboxamides are useful for the control of a broad range of insects and acarids.Type: GrantFiled: August 19, 1982Date of Patent: January 15, 1985Assignee: FMC CorporationInventor: Ernest L. Plummer
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Patent number: 4487953Abstract: Compounds of Formula (I) ##STR1## wherein the 9-bromine atom can be in the .alpha.- or .beta.-position,R.sub.1 is CH.sub.2 OH or C(O)OR.sub.2, wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, or a heterocyclic residue; or R.sub.1 is C(O)NHR.sub.3 wherein R.sub.3 is an acid residue or R.sub.2 ; andA is --CH.sub.2 --CH.sub.2 -- or cis --CH.dbd.CH--;B is --CH.sub.2 --CH.sub.2 --, trans --CH.dbd.CH--, or --C.tbd.C--;W is a free or functionally modified hydroxymethylene group or a free or functionally modified ##STR2## wherein the OH-group can be in the .alpha.- or .beta.-position; D and E together are a direct bond; orD is straight-chain, branched, or cyclic alkylene of 1-10 carbon atoms, optionally substituted by fluorine atoms; andE is oxygen, sulfur, a direct bond --C.tbd.C--, or --CR.sub.6 .dbd.CR.sub.7 --, wherein R.sub.6 and R.sub.7 are different from each other and each is hydrogen, chlorine, or C.sub.1 -C.sub.4 -alkyl;R.sub.4 is a free or functionally modified hydroxy group;R.sub.Type: GrantFiled: December 6, 1982Date of Patent: December 11, 1984Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Norbert Schwarz, Helmut Vorbrueggen, Walter Elger
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Patent number: 4476061Abstract: The present invention relates to 2'-(ortho-chlorobenzoyl)-4'-chloroglycylanilides, compositions thereof, and their use as medicaments, e.g., as anxiolytic agents.The compounds of the invention have the general formula I ##STR1## in which R represents hydrogen or alkyl,R.sub.1 and R.sub.2 may be identical or different and are selected from hydrogen, alkyl, hydroxyalkyl, alkenyl, and alkynyl, possibly substituted by alkyl, and cycloalkyl having three to six members, possibly substituted by alkyl, with the proviso that, when one of R.sub.1 and R.sub.2 represents hydrogen, the other is not lower alkyl or hydroxyalkyl; and with the further proviso that R.sub.1 and R.sub.2 may not simultaneously represent either hydrogen or lower-alkyl. R.sub.1 and R.sub.2 may furthermore form, with the nitrogen atom to which they are connected, a nitrogen heterocycle possibly containing a second heteroatom selected from oxygen and nitrogen.Type: GrantFiled: August 18, 1982Date of Patent: October 9, 1984Assignee: Pierre Fabre, SAInventors: Gilbert Mouzin, Henri Cousse, Antoine Stenger
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Patent number: 4473694Abstract: Process for the synthesis of hindered polysubstituted .alpha.-amino acetamides which comprises first reacting an .alpha.-haloacetamide with a base to form an intermediate .alpha.-lactam which in turn is reacted with a primary or secondary amine. The product thus obtained can comprise a multifunctional compound having one or more hindered amino moieties. These compounds are highly effective as UV stabilizers in a variety of plastics, especially the alpha monoolefins.Type: GrantFiled: September 29, 1982Date of Patent: September 25, 1984Assignee: The B. F. Goodrich CompanyInventor: John T. Lai
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Patent number: 4466980Abstract: A novel compound selected from the group consisting of 7-(or 6- or 4-)thiaprostaglandin E.sub.1 derivatives of the formula (I). ##STR1## wherein A represents --CH.sub.2 -- or ##STR2## in which n is 0, 1 or 2, provided that only one A cut of three is ##STR3## R.sup.1 -R.sup.7 and G are as defined in the specification, the 15-epimers of said thiaprostaglandin E.sub.1 derivatives, the enatiomers of said thiaprostaglandin E.sub.1 derivatives or their 15-epimers, and mixtures of these compounds.A 7-thiaprostaglandin E.sub.1 derivative and/or its optical isomer may be prepared by reacting a 2-organo-2-cyclopentenone (II) with an organic copper-lithium compound (III) to effect conjugation reaction. A 6-thiaprostaglandin E.sub.1 derivative and/or its optical isomer may be prepared by subjecting an .alpha.,.beta.-unsaturated ketone (IV) and a thiol (V) to the Michael addition reaction.Type: GrantFiled: October 30, 1981Date of Patent: August 21, 1984Assignee: Teijin LimitedInventors: Toshio Tanaka, Takeshi Toru, Takeo Oba, Noriaki Okamura, Kenzo Watanabe, Kiyoshi Bannai, Atsuo Hazato, Seizi Kurozumi, Fukuyoshi Kamimoto, Akira Ohtsu
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Patent number: 4456768Abstract: Prostaglandin and prostacyclin compounds which are fluorine substituted in any one or more of the following positions 4,4; 7,7; 10,10; and 5.Type: GrantFiled: May 1, 1981Date of Patent: June 26, 1984Assignee: The University of ChicagoInventor: Josef Fried
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Patent number: 4454339Abstract: 9-Fluoroprostane derivatives of Formula I ##STR1## wherein R.sub.1 is CH.sub.2 OH or ##STR2## wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, or a heterocyclic residue; or R.sub.1 is the residue ##STR3## wherein R.sub.3 is an acid residue or R.sub.2 and A is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH--,B is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH-- or --C.tbd.C,W is a free or functionally modified hydroxymethylene group wherein the OH-group can be in the .alpha.- or .beta.-position,D and E jointly are a direct bond orD is straight-chain or branched alkylene or alkenylene of 1-10 carbon atoms which can optionally be substituted by fluorine atoms, and E is oxygen or sulfur, a direct bond, --C.tbd.C-- or --CR.sub.6 .dbd.CR.sub.7 -- wherein R.sub.6 and R.sub.7 differ from each other and each is hydrogen, chlorine, or alkyl,R.sub.4 is a free or functionally modified hydroxy group, andR.sub.5 is hydrogen, an optionally substituted aliphatic group, e.g.Type: GrantFiled: July 6, 1982Date of Patent: June 12, 1984Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Norbert Schwarz, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Michael-Harold Town
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Patent number: 4444788Abstract: Compounds of the formula ##STR1## wherein the 9-chlorine atom can be in the .alpha.- or .beta.-position,R.sub.1 is OR.sub.2, or NHR.sub.3 wherein R.sub.3 is H or the acyl group ofa C.sub.1-15 hydrocarbon carboxylic or sulfonic acid;A is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH--,B is --CH.sub.2 --CH.sub.2 --,trans--CH.dbd.CH--, or --C.tbd.C--, ##STR2## wherein the OH-group in each case can be in the .alpha.- or .beta.-position, and can be etherified or esterified by tetrahydropyranyl, tetrahydrofuranyl, .alpha.-ethoxyethyl, trimethylsilyl dimethyl, tert-butylsilyl, tribenzylsilyl, acetyl, propionyl, butyryl or benzoyl;D and E together represent a direct bond orD is a straight-chain or branched alkylene group of 1-10 carbon atoms, optionally substituted by fluorine, andE is oxygen or sulfur or a direct bond, andR.sub.4 is hydroxy or hydroxy etherified or esterified as defined for W above;R.sub.5 is a C.sub.1-10 hydrocarbon aliphatic group; a C.sub.Type: GrantFiled: June 10, 1982Date of Patent: April 24, 1984Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Ekkehard Schillinger
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Patent number: 4430336Abstract: N-Substituted 2-methylnaphthylamides of the general formula ##STR1## where R.sup.1 is ##STR2## R.sup.3 being hydrogen or alkoxy, or R.sup.1 is ##STR3## R.sup.4 and R.sup.5 being unsubstituted or substituted alkyl, or R.sup.4 and R.sup.5 together forming a heterocyclic ring which contains two oxygen atoms and is unsubstituted or substituted by alkyl or aryl,R.sup.2 is alkyl which is unsubstituted or substituted by halogen, alkoxy, imidazolyl, pyrazolyl or oxo (.dbd.O), or is alkenyl, alkynyl, cycloalkenyl or alkoxy, or substituted or unsubstituted phenyl, or substituted or unsubstituted hetaryl andX is hydrogen, methyl or halogen, fungicides containing these compounds, and processes for the preparation of the compounds.Type: GrantFiled: November 18, 1980Date of Patent: February 7, 1984Assignee: BASF AktiengesellschaftInventors: Costin Rentzea, Bernd Zeeh, Ernst-Heinrich Pommer
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Patent number: 4425360Abstract: The present invention provides pyruvic acid oximes of the general formula: ##STR1## wherein R is a hydrogen atom, a C.sub.3 -C.sub.8 cycloalkyl, C.sub.1 -C.sub.6 alkoxy, cinnamyloxy, phenylamino, phenyl-N-alkylamino or phenylthio radical or an aryl or aryloxy radical, the aryl moiety of which can be substituted one or more times by C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, halogen, hydroxyl, trifluoromethyl, amino, acetylamino, nitrile, nitro or methylenedioxy, A is a straight-chained or branched, saturated or unsaturated aliphatic hydrocarbon chain containing up to 10 carbon atoms, which can be substituted one or more times by halogen or hydroxyl, and R.sub.1 is a C.sub.1 -C.sub.8 alkyl radical, which can be substituted one or more times by halogen, hydroxyl, nitrile, phenyl or carboxyl, or is a nitrile or formyl group, with the proviso that when R--A-- is a methyl or ethyl radical, R.sub.1 is not a methyl radical or a nitrile group and when R--A-- is a benzyl radical, R.sub.Type: GrantFiled: September 8, 1981Date of Patent: January 10, 1984Assignee: Boehringer Mannheim GmbHInventors: Hans P. Wolff, Ruth Heerdt, Manfred Hubner, deceased, Hans Kuhnle, Felix H. Schmidt
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Patent number: 4419255Abstract: Lubricating oil characterized by improved friction reduction contains friction reducing amounts of a keto amide prepared by the reaction of an amine and an unsaturated cyclic keto acid bearing pendant alkyl groups.Type: GrantFiled: February 1, 1982Date of Patent: December 6, 1983Assignee: Texaco Inc.Inventors: Benjamin J. Kaufman, Robert A. Sawicki, Stephen A. Levine
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Patent number: 4404372Abstract: 15-Substituted-.omega.-pentanorprostaglandin C-1 tetrazoles, imides and sulfonimides.Their use as anti-secretory agents or as agents for the control of fertility.Type: GrantFiled: June 13, 1977Date of Patent: September 13, 1983Assignee: Pfizer Inc.Inventors: Michael R. Johnson, Thomas K. Schaaf, Hans-Jurgen E. Hess
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Patent number: 4403100Abstract: The present invention provides novel (11R)-11-deoxy-11-alkyl-6-oxo-prostaglandins which are useful for curing and preventing duodenal ulcers and for preventing or treating gastrointestinal cell damage caused by the use of other pharmacological agents.Type: GrantFiled: October 30, 1981Date of Patent: September 6, 1983Assignee: The Upjohn CompanyInventor: Douglas R. Morton, Jr.
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Patent number: 4402981Abstract: N.sub.1 -acyl-N.sub.2 -phenyl-1,3-diaminopropan-2-ols are disclosed which possess ulcer-inhibiting activities.Further disclosed are pharmaceutical compositions which are effective in the treatment and prophylaxis of ulcers and which comprise as a pharmacologically active ulcus-inhibiting ingredient N.sub.1 -acyl-N.sub.2 -phenyl-1,3-diaminopropan-2-ols, or a pharmaceutically acceptable acid addition salt thereof, and a pharmaceutically acceptable diluent.Further disclosed are processes for the preparation of the N.sub.1 -acyl-N.sub.2 -phenyl-1,3-diaminopropan-2-ols.Type: GrantFiled: March 16, 1981Date of Patent: September 6, 1983Assignee: Kali-Chemie Pharma, GmbHInventors: Hans Liepmann, Rolf Hueschens, Wolfgang Milkowski, Horst Zeugner, Henning Heinemann, Klaus-Ullrich Wolf, Insa Hell, Reinhard Hempel
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Patent number: 4380667Abstract: The present invention relates to 2'-(ortho-chlorobenzoyl)-4'-chloroglycylanilides, compositions thereof, and their use as medicaments, e.g., as anxiolytic agents.The compounds of the invention have the general formula I ##STR1## in which R represents hydrogen or alkyl,R.sub.1 and R.sub.2 may be identical or different and are selected from hydrogen, alkyl, hydroxyalkyl, alkenyl, and alkynyl, possibly substituted by alkyl, and cycloalkyl having three to six members, possibly substituted by alkyl, with the proviso that, when one of R.sub.1 and R.sub.2 represents hydrogen, the other is not lower alkyl or hydroxyalkyl; and with the further proviso that R.sub.1 and R.sub.2 may not simultaneously represent either hydrogen or lower alkyl. R.sub.1 and R.sub.2 may furthermore form, with the nitrogen atom to which they are connected, a nitrogen heterocycle possibly containing a second heteroatom selected from oxygen and nitrogen.Type: GrantFiled: September 19, 1979Date of Patent: April 19, 1983Assignee: Pierre Fabre S.A.Inventors: Gilbert Mouzin, Henri Cousse, Antoine Stenger
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Patent number: 4370497Abstract: The present invention relates to the use of telluroxides as mild and selective oxidizing agents serving to oxidize certain functions, notably >C.dbd.S groups, in the presence of other relatively easily oxidized functions which remain unaffected; telluroxides of interest as oxidizing agents include, for example, compounds of the formula: ##STR1## wherein R and R.sup.1, which may be the same or different, each represent an optionally substituted aryl or heterocyclic group; or R and R.sup.1 together with the tellurium atom therebetween represent a heterocyclic ring, which may contain one or more further heteroatoms, and which may carry substituents and/or fused aromatic rings.Type: GrantFiled: August 7, 1980Date of Patent: January 25, 1983Inventors: Derek H. R. Barton, Steven V. Ley, Clive A. Meerholz
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Patent number: 4361440Abstract: Compounds of the general structural formula, ##STR1## in which R.sup.1 is C.sub.1 to C.sub.4 lower alkyl, cycloalkyl or alkylamino and R.sup.2 is H or lower N-alkylcarbamyl are made from corresponding m-aminophenylacetylenic compounds by conventional methods and are useful as selective herbicides.Type: GrantFiled: August 31, 1981Date of Patent: November 30, 1982Assignee: Gulf Oil CorporationInventors: Edward T. Sabourin, Charles M. Selwitz
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Patent number: 4359467Abstract: Prostanoic acid derivatives of the formula ##STR1## wherein R.sub.1 is an acid, ester, amide or hydroxyalkylene group; R.sub.2 and R.sub.3 are H or alkyl; R.sub.4 and R.sub.5 are both CH.sub.3 or one is Cl and the other is CH.sub.3 ; A is CH.sub.2 CH.sub.2 or --CH.dbd.CH; B is CH.sub.2 CH.sub.2, trans- ##STR2## W is free or functionally modified hydroxyalkylene or carbonyl; Z is free or functionally modified hydroxymethylene or carbonyl; X Y is either ##STR3## or, when Z is free or functionally modified hydroxymethylene, ##STR4## or, when Z is free or functionally modified carbonyl, --CH.dbd.CH--, R.sub.12 being H, CH.sub.3, CN or free or functionally modified hydroxy; and physiologically acceptable salts thereof when R.sub.1 is an acid group, possess pharmacological activity, including abortion triggering activity.Type: GrantFiled: April 22, 1981Date of Patent: November 16, 1982Assignee: Schering AktiengesellschaftInventors: Helmut Vorbruggen, Norbert Schwarz, Olaf Loge, Walter Elger
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Patent number: 4355045Abstract: The invention relates to topically anti-inflammatory 1-phenylethanolamine derivatives of the general formula I: ##STR1## or acid-addition salts thereof, to pharmaceutical compositions thereof, and to analogy processes for their manufacture. A representative compound is 1-(4-amino-3,5-dichlorophenyl)-2-[1,1-dimethyl-2-(2-phenylacetamido)ethyla mino]ethanol. The derivatives are useful in particular for the treatment of inflammatory diseases or conditions of the skin.Type: GrantFiled: August 3, 1978Date of Patent: October 19, 1982Assignee: Imperial Chemical Industries LimitedInventors: John Preston, Austin J. Reeve
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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: RE31237Abstract: New derivatives of 2-benzoyl-4-nitro anilides, their preparation and their use as medicaments.The new chemical derivatives of the invention have the general formula ##STR1## in which R represents a linear or branched alkyl group, an alkenyl group, a cycloalkyl group or a benzyl group,R.sub.1 represents a hydrogen atom, an alkyl group or a hydroxy alkyl group,R.sub.2 represents a hydroxy-alkyl, alkenyl or alkynyl group, possibly substituted one or more times by an alkyl radical, or a cycloalkyl group having three to six carbon atoms;R.sub.1 and R.sub.2 may furthermore form, with the nitrogen atom to which they are attached, a nitrogen heterocycle containing possibly a second heteroatom selected from among oxygen and nitrogen;under the condition, however, that when R.sub.2 represents a hydroxy-alkyl group R.sub.1 may not be a hydrogen atom.Use as hypnotic agents for the treatment of insomnia.Type: GrantFiled: February 19, 1982Date of Patent: May 10, 1983Assignee: Pierre Fabre S.A.Inventors: Henri Cousse, Gilbert Mouzin
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Patent number: T103403Abstract: This disclosure describes esters having prostaglandin-like activity of 15-deoxy-16-hydroxy-16-substituted-prostanoic acids formed by replacing the hydroxy group of the C.sub.1 -carboxylic acid substituent with para-acetamidophenoxy, methylsulfonylamido, para-acetylphenoxy, para-phenylphenoxy, C.sub.3 -C.sub.10 cycloalkoxy, arylalkoxy wherein the alkoxy group has from 7-12 carbon atoms, phenoxy or phenoxy substituted with 1-3 chlorine atoms or C.sub.1 -C.sub.3 alkyl, phenacyloxy or phenacyloxy ring-substituted with from 1-3 bromine atoms, a nitro moiety, C.sub.1-C.sub.8 arylalkyl, or arylalkoxy wherein the alkoxy group has from 7-12 carbon atoms; substituted arylamino (C.sub.1 -C.sub.12), substituted-naphthoxy, fluorenoxy, carboxyalkoxy (C.sub.5 -C.sub.Type: GrantFiled: May 3, 1982Date of Patent: September 6, 1983Inventors: Martin J. Weiss, Charles V. Grudzinskas, Middleton B. Floyd, Jr., Sow-Mei L. Chen