Carbocyclic Ring Bonded Directly To The -c(=x)- (e.g., 3-benzoyl Pyrrolidine, Etc.) Patents (Class 548/539)
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Patent number: 5171355Abstract: The novel N-acylpyrrolidine derivatives of the formula ##STR1## in which the substituents R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and the index m have the meaning given in the description, are outstandingly suitable for combating nematodes and undesired plant growth.Type: GrantFiled: September 4, 1991Date of Patent: December 15, 1992Assignee: Bayer AktiengesellschaftInventors: Michael Negele, Bernd Baasner, Heinz-Jurgen Bertram, Jurgen Hartwig
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Patent number: 5158970Abstract: New proline derivatives of the general formula: ##STR1## wherein R stands for a lower alkyl group and X for a N-terminal protective group conventional in amino acid chemistry or an acyl group derived from an amino acid with a protective group at the N-terminal. They have inhibitory activity against prolylendopeptidase and are relatively chemically stable as compared with known compounds of this type.Type: GrantFiled: February 8, 1990Date of Patent: October 27, 1992Assignee: Kabushiki Kaisha Yakult HonshaInventors: Takayuki Shioiri, Yasumasa Hamada, Naoko Irako, Kunio Kado
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Patent number: 5157047Abstract: Bis- and tris(trifluoromethyl)arylpyrrole compounds which are effective for the control of insects and acarids are described. A method for the insecticidal and acaricidal use of said compounds and methods for the preparation of said compounds are presented.Type: GrantFiled: October 18, 1990Date of Patent: October 20, 1992Assignee: American Cyanamid CompanyInventors: Venkataraman Kameswaran, Victor M. Kamhi
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Patent number: 5102896Abstract: 1-acyl-2-pyrrolidinones of general formula (I) ##STR1## wherein R is selected from the group consisting of: phenyl substituted with halogen-substituted lower (C.sub.1 -C.sub.4) alkyl;phenylalkyl wherein the alkyl moiety has 2-4 carbon atoms;phenylalkenyl wherein the alkenyl moiety has 2-4 carbon atoms and the phenyl moiety is substituted with halogen-substituted lower (C.sub.1 -C.sub.4)alkyl;N-substituted pyrrolidin-2-yl; andpyrid-3-yl are potent enhancers of learning and memory.Orally or parenterally administrable pharmaceutical compositions in unit dosage form comprise from about 100 to 500 mg of one of the compound of formula (I).Type: GrantFiled: June 11, 1990Date of Patent: April 7, 1992Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.Inventors: Fabio Giannessi, Orlando Ghirardi, Domenico Misiti, Maria O. Tinti
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Patent number: 5099032Abstract: A process for the preparation of enantiomerically homogeneous aminopyrrolidinyl naphthyridine carboxylic acids and quinolone carboxylic acids, and for the preparation of intermediates that are useful in the production of these carboxylic acids.Type: GrantFiled: June 1, 1990Date of Patent: March 24, 1992Assignee: Abbott LaboratoriesInventor: Daniel Tim-Wo Chu
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Patent number: 5091407Abstract: Fungicidally active compounds of the formula ##STR1## and steroisomers thereof, wherein A is the group .dbd.CW--or a nitrogen atom, B is the group .dbd.CX--or a nitrogen atom, D is the group .dbd.CY--or a nitrogen atom, and E is the group .dbd.CZ--or a nitrogen atom, wherein W, X, Y and Z, which may be the same or different, are, for example, hydrogen, halogen, nitro, nitrile, or other defined groups and wherein R.sup.1 and R.sup.2 are alkyl, cycloalkyl, alkenyl, alkynyl, optionally substituted aryl, optionally substituted aralkyl, cycloalkyl groups, or optionally substituted heteroaromatic, and V is oxygen or sulfur.Type: GrantFiled: November 24, 1989Date of Patent: February 25, 1992Assignee: Imperial Chemical Industries PLCInventors: Paul deFraine, Brian K. Snell, Kevin Beautement, Vivienne M. Anthony, John M. Clough
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Patent number: 5086054Abstract: Novel arylcycloalkanepolyalkylamines useful as anti-psychotic, anti-ischemia, anti-stroke, anti-dementia and anti-convulsant agents. These arylcycloalkanepolyalkylamines are selective high-affinity ligands to the sigma binding-sites containing three basic units: arylcycloalkyl group, an amine group and an intermediate chain. Their preparation and use for treatment of psychoses, ischemia, stroke, dementia and convulsions are also disclosed.Type: GrantFiled: July 31, 1990Date of Patent: February 4, 1992Assignee: SRI InternationalInventor: Daniel W. Parish
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Patent number: 5082950Abstract: 5-Aroyl-2,3-dihydro-1H-pyrrolizine-1,1-dicarboxylates of the formula ##STR1## are prepared from 2-aroylpyrroles. Hydrolysis and mono-decarboxylation of these compounds affords ketorolac and related compounds.Type: GrantFiled: October 12, 1990Date of Patent: January 21, 1992Assignee: Syntex (U.S.A.) Inc.Inventors: Joseph M. Muchowski, In-Seop Cho
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Patent number: 5082951Abstract: 5-Aroyl-2,3-dihydro-1H-pyrrolizine-1,1-dicarboxylates of the formula ##STR1## are prepared from 2-aroylpyrroles. Hydrolysis and mono-decarboxylation of these compounds affords ketorolac and related compounds.Type: GrantFiled: October 12, 1990Date of Patent: January 21, 1992Assignee: Syntex (U.S.A.) Inc.Inventors: Joseph M. Muchowski, In-Seop Cho
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Patent number: 5079248Abstract: A series of [N-alkyl-N-(nitro-, alkylsulphonamido, or amino-phenalkyl) amino]-alkyl, alkoxy or alkylthio phenyl derivatives having utility as anti-arrhythmic agents.Type: GrantFiled: June 20, 1990Date of Patent: January 7, 1992Assignee: Pfizer Inc.Inventors: Peter E. Cross, Geoffrey N. Thomas, John E. Arrowsmith
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Patent number: 5077288Abstract: The invention relates to the compounds of general formula I: ##STR1## in which: m represents an integer from 2 to 4,n and p, which may be identical or different, each represent an integer from 1 to 3,q represents 0 or 1, andR represents:either a group of formula (A): ##STR2## or a radical of formula (B): ##STR3## or a 2,4-dioxo-1,2,3,4-tetrahydroquinazolinyl radical, on condition, however, that, in this case, n and p do not simultaneously represent the number 2,or a benzhydryloxy group,or a 1-oxophthalazinyl radical,or a 5-oxothiazolo[3,2-A]pyrimidinyl radical,or a group of formula C: ##STR4## their possible stereoisomers and their addition salts with a pharmaceutically acceptable inorganic or organic acid.The compounds of formula I are medicinal products with useful 5-HT.sub.2 - and .alpha..sub.1 -antagonistic activities.Type: GrantFiled: March 20, 1990Date of Patent: December 31, 1991Assignee: Adir et CompagnieInventors: Gilbert Lavielle, Francis Colpaert, Michel Laubie
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Patent number: 5073188Abstract: Compounds of the formula ##STR1## wherein x is a hydrogen atom, a halogen atom, a trihalomethyl group, an alkyl group, or a cyano group,Y is a hydrogen atom or a halogen atom,R.sup.1 is a hydrogen atom, a hydroxy group, an alkoxy group, or an optionally-substituted alkyl group, andR.sup.2 is a hydrogen atom or an optionally-substituted alkyl group, or R.sup.1 and R.sup.2 can be taken together to form a heterocyclic ring,and compositions containing these compounds exhibit herbicidal activity.Type: GrantFiled: September 8, 1987Date of Patent: December 17, 1991Assignee: Rohm and Haas CompanyInventor: Wayne O. Johnson
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Patent number: 5051444Abstract: The present invention relates to pyrrolidine derivatives of the formula ##STR1## wherein R.sup.1 and R.sup.2 are defined as herein. The compounds are useful as anti-amnestic agent.Type: GrantFiled: September 18, 1989Date of Patent: September 24, 1991Assignee: Sumitomo Pharmaceuticals Company, LimitedInventors: Katsumi Tamoto, Renzo Ohuchi, Keiichi Ono
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Patent number: 5049578Abstract: Antihypercholesterolemic activity is exhibited by novel compounds of the formula ##STR1## wherein: Z is ##STR2## X is lower alkyl or lower alenyl; R.sup.1 is aryl or alkyl;R.sup.2 and R.sup.3 are the same or different and are hydrogen, or lower alkyl or aryl, or R.sup.2 and R.sup.3 taken together to form a cycloalkyl group; andR.sup.4 is hydrogen, lower alkyl, or alkali metal (such as sodium, lithium, or potassium) or a radical such as ammonium.Methods of use and novel intermediates of these compounds are also provided.Type: GrantFiled: March 9, 1990Date of Patent: September 17, 1991Assignee: E. R. Squibb & Sons, Inc.Inventors: Ravi K. Varma, Eric M. Gordon
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Patent number: 5041442Abstract: This invention is directed to compounds of formula (I): ##STR1## wherein R.sup.1 is thiocyano, --CH.sub.2 CN, --NH.sub.2, --NHR.sup.5, or --CH.sub.2 OR.sup.5 where R.sup.5 is lower alkyl;R.sup.2 is hydrogen, halo, lower alkyl, or lower alkylthio;R.sup.3 is hydrogen, halo, lower alkyl, lower alkylthio, or thiocyano;R.sup.4 is hydrogen, halo, lower alkyl, lower alkoxy, lower alkylthio, or lower alkylsulfonyl; andY is --O--CH.sub.2 --, --S--CH.sub.2 --, --CH.dbd.CH--, or --(CH.sub.2).sub.n -- where n is 0, 1, 2, 3 or 4;or a pharmaceutically acceptable salt thereof. These compounds are useful in treating mammals having disease-states characterized by excessive gastric acid secretion.Type: GrantFiled: July 31, 1990Date of Patent: August 20, 1991Assignee: Syntex (U.S.A.) Inc.Inventors: Ruth S. Romero, Fidencio Franco, Armando C. Castaneda, Joseph M. Muchowski
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Patent number: 5036153Abstract: (R,R)-2,5-Diazabicyclo[ 2.2.1]heptanes are prepared from a compound of the formula ##STR1## wherein X and R.sub.2 are as defined herein, by heating with tosylchloride in pyridine, reacting the formed compound of the formula ##STR2## with a C.sub.1 -C.sub.6 alkylamine or ammonia, and reducing or hydrolyzing the formed compound of the formula ##STR3## wherein R.sub.1 is hydrogen or C.sub.1 -C.sub.6 alkyl.Type: GrantFiled: October 18, 1989Date of Patent: July 30, 1991Inventors: Tamim F. Braish, Darrell E. Fox
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Patent number: 5028604Abstract: Novel condensed benzene derivatives having prolyl endopeptidase inhibitory, anti-hypoxic, and anti-amnesic activities are disclosed. The compounds are represented by the following (I), ##STR1## wherein A represents a methylene, ethylene, or propylene group, B represents a methylene or ethylene group, m denotes an integer of 0-5, X and Y, which may be same or different, individually represent a methylene group or sulfur atom, R.sup.1 represents a hydrogen atom, a carboxyl, lower alkyloxycarbonyl, hydroxymethyl, or formyl group, R.sup.2 represents a hydrogen atom, a halogen atom, a lower alkyl, lower alkoxy, nitro, or amino group, R.sup.3 represents a hydrogen atom or a lower alkyl group, and the dotted line may optionally be present. They are useful as a medicine for treating or preventing cerebral circulation disorder, cerebral metabolism disorder, or memory disturbance.Type: GrantFiled: December 1, 1989Date of Patent: July 2, 1991Assignee: Zeria Pharmaceutical Co., Ltd.Inventors: Motoki Torizuka, Tomoji Aotsuka, Mitsuo Soeda, Kuniyoshi Ogura, Yoshiaki Tanaka, Hisayoshi Kato, Naoki Nakata, Naoyoshi Miura, Hikari Morita
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Patent number: 5021414Abstract: A phenol derivative of the formulaNU--A--X--R.sup.1wherein NU is a defined bis-phenolic nucleus including a hydroxyphenyl-hydroxynaphthyl; hydroxyphenyl-hydroxyindanyl, hydroxyphenyl-hydroxybenzothienyl or di-hydroxyphenyl-ethylene or vinylene nucleus;wherein A is alkylene, alkenylene or alkynylene which may be interrupted by phenylene or other linkages,wherein R.sup.1 is hydrogen, or alkyl, alkenyl, cycloalkyl, halogenoalkyl, aryl or arylalkyl, or R.sup.1 is joined to R.sup.2, and wherein X is --CONR.sup.2 --, --CSNR.sup.2 --, --NR.sup.12 CO--, --NR.sup.12 CS--, --NR.sup.12 CONR.sup.2 --, ##STR1## --SO.sub.2 NR.sup.2 -- or --CO--, or, when R.sup.1 is not hydrogen, is --NR.sup.12 COO--, --S--, --SO-- or --SO.sub.2 --,wherein R.sup.2 is hydrogen or alkyl, or R.sup.1 and R.sup.2 together form alkylene;wherein R.sup.12 is hydrogen or alkyl, and wherein R.sup.22 is hydrogen, cyano or nitro;or a salt thereof when appropriate.Type: GrantFiled: December 18, 1989Date of Patent: June 4, 1991Assignee: Imperial Chemical Industries PLCInventors: William R. Pilgrim, Derek W. Young, Brian S. Tait, Graham C. Crawley, Philip N. Edwards, George B. Hill
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Patent number: 5017610Abstract: A derivative of general formula: ##STR1## wherein Y is --SO.sub.2 -- or ##STR2## (i) R.sup.1 and R.sup.2, which may be the same or different, each represent, (1) --H, (2) C1-16 alkyl or (3) the formula: --X-- .circle.A --(R.sup.4).sub.n wherein X is a single-bond, --SO.sub.2 --, C1-4 alkylene, C1-4 alkylene substituted by ##STR3## -- .circle.A -- is carbocyclic or heterocyclic ring, n is 1.about.5, R.sup.4 is (1) --H or C1-8 alkyl, (2) C1-14 alkoxy, (3) C1-6 alkylthio, (4) --OH, halogen, --NO.sub.2 or trihalomethyl, (5) the formula: --NR.sup.41 R.sup.42 wherein R.sup.41 and R.sup.42 each represents halogen or C1-4 alkyl, (6) tetrazole, (7) --SO.sub.3 H or --CH.sub.2 OH, (8) the formula: --SO.sub.2 NR.sup.41 R.sup.42 (9) the formula: --Z.sup.41 --COOR.sup.43 wherein Z.sup.41 is single-bond, C1-4 alkylene or C2-4 alkenylene, R.sup.43 is --H, C1-4 alkyl or benzyl, (10) the formula: --CONR.sup.41 R.sup.42 (11) the formula: --COO--Z.sup.42 --COOR.sup.43 wherein Z.sup.42 is C1-4 alkylene, R.sup.Type: GrantFiled: June 12, 1989Date of Patent: May 21, 1991Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Katsuhiro Imaki, Yoshinobu Arai, Tadao Okegawa
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Patent number: 5003081Abstract: Pyrrole derivatives of the formula ##STR1## or the tautomers thereof, where R.sup.1 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, hetaryl or amino, it being possible for these radicals to be substituted,R.sup.2 is hydrogen, alkyl, benzyl, alkenyl, cycloalkyl or phenylR.sup.3 is hydrogen, alkyl, benzyl or alkenyl, or R.sup.2 and R.sup.3 together are ##STR2## where T.sup.1, T.sup.2 and T.sup.3 have the meanings mentioned in the description, or R.sup.2 and R.sup.3 together with the nitrogen connecting them are a heterocyclic radical,R.sup.4 is cyano, or carbamoyl or thiocarbamoyl, each of which can be substituted, or --C(NH.sub.2).dbd.N--OH,R.sup.5 is halogen, hydroxyl, alkanoyloxy or benzoyloxy andR.sup.6 is hydrogen, alkyl, phenyl, cyano, halogen, nitro, hydroxysulfonyl, alkanoyl, benzoyl or ##STR3## where T.sup.4 is alkyl or phenyl and T.sup.5 is the radical of an active methylene compound, hydroxyimino or the radical of a primary amine,with the proviso that R.sup.1, R.sup.2 and R.sup.Type: GrantFiled: January 8, 1990Date of Patent: March 26, 1991Assignee: BASF AktiengesellschaftInventors: Juergen Pfister, Matthias Wiesenfeldt, Karl-Heinz Etzbach
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Patent number: 4988822Abstract: 5-Aroyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1,1-dicarboxylates of the formula ##STR1## are prepared from 2-halopyrroles. Hydrolysis and .beta.-decarboxylation of these compounds affords ketorolac and related compounds.Type: GrantFiled: July 27, 1989Date of Patent: January 29, 1991Assignee: Syntex (U.S.A.) Inc.Inventors: Joseph M. Muchowski, Robert Greenhouse
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Patent number: 4985435Abstract: 2-Substituted-1-naphthols are 5-lipoxygenase inhibitors which make them useful in the treatment of inflammation, obstructive lung diseases and/or psoriasis. Useful 2-substituent groups are alkyls, alkenyls, alkynyls, cycloalkyls, cycloalkenyls, the groups CH.sub.2 --C.tbd.C--(CH.sub.2).sub.m R.sup.5 and CH.dbd.CH--(CH.sub.2).sub.n R.sup.5 (where m is 1-4, n is 0-3 and R.sup.5 includes phenyl, COOR.sup.9, where R.sup.9 is H or alkyl of 1-4 carbons, AR.sup.6 l (where A is a methylene chain and R.sup.6 is a variety of groups including Cl, Br, I, CHO, CN, COOR.sup.9, NH.sub.2, SC(NH)NH.sub.2, phenyl, P(O)(OR.sup.9).sub.2, etc.), and CHR.sup.7 R.sup.21 (where R.sup.7 is a variety of aromatic and heterocyclic groups and R.sup.21 is H, optionally substituted phenyl and a variety of heterocyclic groups).Type: GrantFiled: March 16, 1989Date of Patent: January 15, 1991Assignee: E. I. Du Pont de Nemours and CompanyInventor: Douglas G. Batt
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Patent number: 4983624Abstract: A novel prolinal derivative of general formula: ##STR1## [whereinA represents a group of the general formula: ##STR2## (wherein one of R.sup.1 and R.sup.2 represents hydrogen atom and the other represents alkyl group of from 2 to 5 carbon atoms, alkoxy group of from 1 to 5 carbon atom(s), phenyl group, benzyl group, cycloalkyl group of from 4 to 6 carbon atoms or (cycloalkyl group of from 4 to 6 carbon atoms) - methyl group or R.sup.1 and R.sup.2 each represents, same or different, alkyl group of from 1 to 4 carbon atom(s).)or a group of the general formula: ##STR3## (wherein m represents an integer of from 3 to 6.) n represents an integer of from 3 to 10.D represents carbocyclic or heterocyclic ring unsubstituted or substituted by from one to three of halogen atom, nitro group, trifluoromethyl group, alkyl or akloxy group of from 1 to 4 carbon atom(s).]possess inhibitory activity on prolyl endopeptidase, and therefore be useful for treating and/or preventing agent for amnesia.Type: GrantFiled: December 29, 1987Date of Patent: January 8, 1991Assignee: Ono Pharmaceutical Co., LtdInventors: Masaaki Toda, Shuichi Ohuchida, Hiroyuki Ohno
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Patent number: 4977275Abstract: A pyrrole derivative having excellent anti-microbial activities is disclosed. This compound is represented by the following formula (I): ##STR1## wherein X.sub.1 and X.sub.2 are the same or different and mean individually a halogen atom, R.sub.1 denotes an alkyl, cycloalkyl, haloalkyl, alkenyl, substituted or unsubstituted phenyl, substituted or unsubstituted aralkyl group or a group --COR.sub.3 in which R.sub.3 is an alkyl group having at least five carbon atoms or a cycloalkyl, haloalkyl, alkenyl, substituted or unsubstituted phenyl, substituted or unsubstituted aralkyl, or heterocyclic group, and R.sub.2 stands for a hydrogen or halogen atom or an alkyl group, with a proviso that R.sub.1 is other than a hydrogen atom or methyl group when X.sub.1, X.sub.2 and R.sub.2 are each a bromine atom.Type: GrantFiled: April 5, 1989Date of Patent: December 11, 1990Assignee: SS Pharmaceutical Co., Ltd.Inventors: Hiroshi Hasegawa, Kinichi Mogi, Noriaki Shioiri, Susumu Sato, Tatsuhiko Katori
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Patent number: 4977180Abstract: A novel prolinal derivative of general formula: ##STR1## wherein A represents alkylene group of from 1 to 4 carbon atom(s) or saturated hydrocarbon ring of from 3 to 7 carbon atoms, n represents a number 2, 3 or 4, D represents carbocyclic or heterocyclic ring unsubstituted or substituted by from one to three of halogen atom, alkyl or alkoxy group of from 1 to 4 carbon atom(s), nitro group or trifluromethyl group posses inhibitory activity on prolyl endopeptidase, and therefore are useful for treating and/or preventing agent for amnesia.Type: GrantFiled: February 3, 1988Date of Patent: December 11, 1990Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Masaaki Toda, Shuichi Ohuchida, Hiroyuki Ohno
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Patent number: 4975444Abstract: Compounds of the formula ##STR1## wherein A is a carbocyclic, saturated or unsaturated ring; R.sup.1 is hydrogen or alkyl; R and R.sup.4 are each alkyl, cycloalkyl, benzyl or a readily hydrolyzable ester group; Y is a bond or a straight or branch alkylene; R.sup.2 is hydrogen, aryl, heterocyclic, R.sup.6 CONR.sup.5, R.sup.7 NR.sup.5 CO, R.sup.7 NR.sup.5 SO.sub.2 --or R.sup.8 SO.sub.2 NR.sup.5 --where R.sup.5 is hydrogen, alkyl or aralkyl; R.sup.6 is alkyl, aryl, aralkyl, heterocyclic, heterocyclyalkyl or a group of the formula ##STR2## where R.sup.9 is hydrogen, hydroxy, alkoxy, alkyl, hydroxyalkyl, aralkyl, alkylene, heterocyclic, heterocyclylalkyl, R.sup.12 CONH--, R.sup.12 SO.sub.2 NH-- or (R.sup.13).sub.2 N--; R.sup.10 and R.sup.11 are each hydrogen or alkyl; or R.sup.10 is hydrogen and R.sup.11 is aminoalkyl, imidazolylmethyl, aryl, aralkyl, aralkoxyalkoxy, hydroxyalkyl or methylthioalkyl; or R.sup.10 and R.sup.Type: GrantFiled: August 25, 1989Date of Patent: December 4, 1990Assignee: Pfizer Inc.Inventors: John C. Danilewicz, Keith James, Ryszard J. Kobylecki
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Patent number: 4968677Abstract: 1-Aryl-2-naphthoylamines of formula I are described ##STR1## wherein R.sub.1 is halogen, nitro, cyano, C.sub.1 -C.sub.6 alkyl that is unsubstituted or mono- or poly-substituted by halogen and/or C.sub.1 -C.sub.3 alkoxy, or is C.sub.3 -C.sub.6 cycloalkyl, OR.sub.4, NR.sub.5 R.sub.6, CO2R.sub.5, CONR.sub.5 R.sub.6 or NHCOR.sub.7, or wherein two adjacent positions in the nucleus are bridged by a methylenedioxy or ethylenedioxy group that is unsubstituted or mono- or poly-substituted by fluorine, wherein further R.sub.4 is hydrogen or C.sub.1 -C.sub.6 alkyl that is unsubstituted or substituted by C.sub.1 -C.sub.3 alkoxy or mono- or poly-substituted by halogen, or is C.sub.3 -C.sub.4 alkenyl, 2-propynyl, 3-halo-2-propynyl, ##STR2## or COR.sub.7, each of R.sub.5 and R.sub.6, independently of the other, is H or C.sub.1 -C.sub.4 alkyl, R.sub.7 is C.sub.1 -C.sub.Type: GrantFiled: June 14, 1989Date of Patent: November 6, 1990Assignee: Ciba-Geigy CorporationInventor: Peter Riebli
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Patent number: 4966901Abstract: Pyrrole derivatives of the general formula I ##STR1## wherein R denotes alkyl which is substituted by --NH.sub.2 or acylamino, R.sup.1 and R.sup.2 independently of one another denote hydrogen or alkyl having 1 to 4 carbon atoms, R.sup.3 denotes hydrogen, alkyl having 1 to 4 carbon atoms or a carboxylic acid grouping, R.sup.Type: GrantFiled: May 23, 1989Date of Patent: October 30, 1990Assignee: Cassella AktiengesellschaftInventors: Gerhard Zoller, Rudi Beyerle, Ursula Schindler
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Patent number: 4958030Abstract: 3-Phenylpyrrole derivatives of formula I ##STR1## wherein X is cyano, --CO--R.sub.3, --CO--OR.sub.3 or ##STR2## R.sub.1 and R.sub.2 are each independently of the other hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, nitro, cyano, halogen or C.sub.1 -C.sub.6 haloalkyl, orR.sub.1 and R.sub.2, when taken together, are methylenedioxy or difluoromethylenedioxy,R.sub.3 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, phenyl or benzyl, or phenyl or benzyl which are each substituted by halogen, methyl, methoxy or methylthio, andR.sub.4 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.Type: GrantFiled: October 11, 1989Date of Patent: September 18, 1990Assignee: Ciba-Geigy CorporationInventors: Rudolf W. Pfluger, Jean Indermuhle, Franz Felix
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Patent number: 4948804Abstract: Compounds useful in the treatment of patients suffering from intellectual or nervous asthenias, memory failures, senescence or mental strain of the formula (I): ##STR1## in which R' represents hydrogen, linear, branched or cyclic alkyl containing up to 12 carbon atoms, alkenyl containing from 2 to 8 carbon atoms, acyl containing from 1 to 6 carbon atoms or aralkyl containing from 7 to 15 carbon atoms and R represents aryl containing up to 14 carbon atoms, optionally substituted, or a mono- or polycryclic heterocyclic aromatic radical, optionally substituted; also therapeutic compositions containing those compounds and method of use.Type: GrantFiled: June 24, 1988Date of Patent: August 14, 1990Assignee: Roussel UclafInventors: Giulio Galliani, Fernando Barzaghi, Carlo Zirotti, Emilio Toja
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Patent number: 4943310Abstract: The invention relates to new 4-benzoyl-3-hydroxy-5-oxo-3-cyclohexenecarboxylic acid derivatives of general formula I ##STR1## in which A, B, R.sup.1, R.sup.2, R.sup.2 and R.sup.3 have the meanings given in the description, and their use as plant growth regulants.Type: GrantFiled: December 16, 1988Date of Patent: July 24, 1990Assignee: Schering AktiengesellschaftInventors: Alfred Angermann, Helga Franke, Gerhard Johann
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Patent number: 4940696Abstract: A benzonaphthalene compound has the formula ##STR1## wherein R.sub.1 represents ##STR2## or (ii) --CH.sub.2 OH; R.sub.6 represents ##STR3## or OR.sub.7 wherein R.sub.7 represents hydrogen, alkyl having 1-20 carbon atoms, monohydroxyalkyl or polyhydroxyalkyl, r' or r" represent hydrogen, lower alkyl, mono or polyhydroxyalkyl, aryl or a residue of an amino acid or a sugar, or together form a heterocycle; R.sub.2 represents hydrogen, alkyl having 1-15 carbon atoms, alkoxy having 1-4 carbon atoms or a cycloaliphatic radical; R.sub.3 represents hydrogen, hydroxy, alkyl having 1-4 carbon atoms, alkoxy having 1-10 carbon atoms, a cycloaliphatic radical, a thiocycloaliphatic radical or --O--Si(CH.sub.3).sub.2 --R.sub.8 wherein R.sub.8 represents lower alkyl; and R.sub.4 and R.sub.5 represent hydrogen, lower alkyl, hydroxy or lower acyloxy.This compound is useful in the topical and systemic treatment of dermatologic diseases and in the treatment of the degeneration of conjunctive tissues.Type: GrantFiled: November 16, 1987Date of Patent: July 10, 1990Assignee: Centre International de Recherches Dermatologioues (CIRD)Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
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Patent number: 4933467Abstract: Cyclic imides are prepared by reacting carbon monoxide with an ortho dihalide aromatic compound or a cis-1,2-vinyl dihalide and an amide in the presence of palladium catalyst and a base. The process is preferably conducted in the presence of a dipolar aprotic solvent as a liquid reaction medium.Type: GrantFiled: September 11, 1989Date of Patent: June 12, 1990Assignee: Eastman Kodak CompanyInventors: Robert J. Perry, S. R. Turner
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Patent number: 4933460Abstract: Novel 3-(piperidinyl)- and 3-(pyrrolidinyl)-1H-indazoles, intermediates and processes for the preparation thereof, and methods for treating psychoses, treating depression, alleviating pain, treating convulsions and treating hypertension utilizing compounds or compositions thereof are disclosed.Type: GrantFiled: May 13, 1989Date of Patent: June 12, 1990Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventor: Joseph T. Strupczewski
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Patent number: 4933468Abstract: Amide-imides are prepared by reacting carbon monoxide with an ortho dihalide aromatic compound or a cis-1,2-vinyl dihalide having an isolated halogen function, and with an amine, in the presence of palladium catalyst and a base. The process is preferably conducted in the presence of a dipolar aprotic solvent as a liquid reaction medium.Type: GrantFiled: September 11, 1989Date of Patent: June 12, 1990Assignee: Eastman Kodak CompanyInventors: Robert J. Perry, S. Richard Turner
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Patent number: 4933466Abstract: Cyclic imides are prepared by reacting carbon monoxide with an ortho dihalide aromatic compound or a cis-1,2-vinyl dihalide and an amine in the presence of palladium catalyst and a base. The process is preferably conducted in the presence of a dipolar aprotic solvent as a liquid reaction medium.Acyclic imides are prepared by reacting CO with an activated halide and an amide (primary or secondary) in the presence of a Pd catalyst and a base.Type: GrantFiled: January 17, 1989Date of Patent: June 12, 1990Assignee: Eastman Kodak CompanyInventors: Robert J. Perry, Sam R. Turner
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Patent number: 4921863Abstract: Cyclic amine derivatives of the formula: ##STR1## or the pharmacologically acceptable salts thereof, wherein the symbols are as defined in the specification, as effective in relieving, curing or preventing mental symptoms due to cerebral vascular disorders.Type: GrantFiled: February 17, 1988Date of Patent: May 1, 1990Assignee: Eisai Co., Ltd.Inventors: Hachiro Sugimoto, Takaharu Nakamura, Norio Karibe, Isao Saito, Kunizou Higurashi, Masahiro Yonaga, Takeru Kaneko, Takahiro Nakazawa, Masataka Ueno, Kiyomi Yamatsu
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Patent number: 4912232Abstract: The invention is a process for the preparation of a N-hydrocarbylcarbonyl-5-(1-hydrocarbylcarbonyloxy)hydrocarbylpyrrolidin-2- one which comprises contacting in an inert nonpolar organic solvent a hydrocarbyloxycarbonylpyrrolidin-2-one with(a) an agent which forms a nitrogen-metal or nitrogen-metalloid bond;(b) a reducing agent;(c) an alkylating agent; and(d) an acylating agent;under conditions such that a N-hydrocarbylcarbonyl-5-(1-hydrocarbylcarbonyloxy)hydrocarbylpyrrolidin-2- one is prepared.Type: GrantFiled: August 4, 1987Date of Patent: March 27, 1990Assignee: Dow Chemical CompanyInventors: Michael J. Mullins, Edmund P. Woo
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Patent number: 4904661Abstract: A phenol derivative of the formulaNU--A--X--R.sup.1wherein NU is a defined bis-phenolic nucleus including a hydroxyphenyl-hydroxynaphthyl; hydroxyphenyl-hydroxyindanyl, hydroxyphenyl-hydroxybenzothienyl or di-hydroxyphenyl-ethylene or vinylene nucleus;wherein A is alkylene, alkenylene or alkynylene which may be interrupted by phenylene or other linkages,wherein R.sup.1 is hydrogen, or alkyl, alkenyl, cycloalkyl, halogenoalkyl, aryl or arylalkyl, or R.sup.1 is joined to R.sup.2, and wherein X is --CONR.sup.2 --, --CSNR.sup.2 --, --NR.sup.12 CO--, --NR.sup.12 CS--, --NR.sup.12 CONR.sup.2 --, ##STR1## --SO.sub.2 NR.sup.2 -- or --CO--, or, when R.sup.1 is not hydrogen, is --NR.sup.12 COO--, --S--, --SO-- or --SO.sub.2 --, wherein R.sup.2 is hydrogen or alkyl, or R.sup.1 and R.sup.2 together form alkylene;wherein R.sup.12 is hydrogen or alkyl, and wherein R.sup.22 is hydrogen, cyano or nitro;or a salt thereof when appropriate.Type: GrantFiled: December 16, 1987Date of Patent: February 27, 1990Assignee: Imperial Chemical Industries PLCInventors: William R. Pilgrim, Derek W. Young, Brian S. Tait, Graham C. Crawley, Philip N. Edwards, George B. Hill
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Patent number: 4880827Abstract: Pyrrolidine derivatives having inhibitory action for proline-specific endopeptidase which are useful for anti-amnestic agent. The disclosed pyrrolidine derivatives as well as their acid addition salts can be administered orally or parenterally in the form of conventional pharmaceutical preparations. For instance, they can be administered orally in the form of conventional solid pharmaceutical preparations such as tablets, capsules, syrups and suspensions. Alternatively, they can be administered parenterally by injection in the form of conventional liquid pharmaceutical preparations such as solutions, emulsions, suspensions, etc. Also, they may be directly applied to rectum in the form of suppository. Further, the preparations may contain physiologically acceptable carriers, excipients, activators, binding agents, stabilizers, etc. In the case of injections, physiologically acceptable buffers, solubilizing agents or isotonic agents may be incorporated therein. Methods of production are also disclosed.Type: GrantFiled: March 13, 1987Date of Patent: November 14, 1989Assignee: Sumitomo Pharmaceuticals Company, Ltd.Inventors: Katsumi Tamoto, Renzo Ohuchi, Keiichi Ono
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Patent number: 4871857Abstract: Compounds having the formula ##STR1## wherein R is halogen; C.sub.1-C.sub.2 alkyl; C.sub.1-C.sub.2 alkoxy; nitro; cyano; C.sub.1-C.sub.2 haloalkyl; or R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1-C.sub.2 alkyl; R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.1 and R.sup.2 together are alkylene having 2-5 carbon atoms; R.sup.3 is hydrogen or C.sub.1 -C.sub.4 aklyl; R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.3 and R.sup.4 together are carbonyl; and R.sup.5 and R.sup.6 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.m -- wherein m is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.c R.sup.d wherein R.sup.c and R.sup.d independently are hydrogen or C.sub.1 -C.sub.Type: GrantFiled: November 7, 1988Date of Patent: October 3, 1989Assignee: Stuaffer Chemical CompanyInventor: Jeff K. Curtis
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Patent number: 4871856Abstract: Compounds having the formula ##STR1## wherein R is halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; or R.sup.a SO.sub.n --wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl; R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.1 and R.sup.2 together are alkylene having 2-5 carbon atoms; R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.3 and R.sup.4 together are carbonyl; and R.sup.5 and R.sup.6 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.m --wherein m is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 - C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.c R.sup.d wherein R.sup.c and R.sup.d independently are hydrogen or C.sub.1 -C.Type: GrantFiled: November 7, 1988Date of Patent: October 3, 1989Assignee: Stauffer Chemical CompanyInventor: Jeff K. Curtis
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Patent number: 4851426Abstract: Novel esters of the general formula ##STR1## in which ##STR2## is the acyl residue of a non-steroidal anti-inflammatory compound containing a carboxylic acid function. The novel esters are prepared by reacting an acide R--COOH when R is as above, with 1-haloethyl ethyl carbonate. There are also provided pharmaceutical compositions containing any of the said novel esters.Type: GrantFiled: February 12, 1986Date of Patent: July 25, 1989Assignee: Teva Pharmaceutical Industries, Ltd.Inventors: David Ladkani, Haim Yellin, Ben Z. Weiner, David Avnir
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Patent number: 4833155Abstract: 3-[.omega.-(3,5-Di-t-butyl-4-hydroxyphenyl)alkanoyl]-pyrroles and their de-oxy analogs, for example, 3-(3,5-di-t-butyl-4-hydroxybenzyl)pyrrole, 2-chloro-4-(3,5-di-t-butyl-4-hydroxybenzoyl)pyrrole, 3-(3,5-di-t-butyl-4-hydroxybenzoyl)pyrrole and 3-[2-(3,5-di-t-butyl-4-hydroxyphenyl)-1-oxoethyl]pyrrole, have high pharmacological potency as anti-inflammatory, analgesic and antipyretic agents.Type: GrantFiled: November 25, 1986Date of Patent: May 23, 1989Assignee: Syntex (U.S.A.) Inc.Inventors: Joseph M. Muchowski, Robert Greenhouse, John Young, D. V. Krishna Murthy
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Patent number: 4808720Abstract: Compounds having the formula ##STR1## wherein R is halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; or R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl; R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.1 and R.sup.2 together are alkylene having 2-5 carbon atoms; R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.3 and R.sup.4 together are carbonyl; and R.sup.5 and R.sup.6 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethyoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.m -- wherein m is the integer 0, 1 or 2; and R.sup.b is (a) C.sub. 1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.c R.sup.d wherein R.sup.c and R.sup.d independently are hydrogen or C.sub.Type: GrantFiled: March 13, 1987Date of Patent: February 28, 1989Assignee: Stauffer Chemical CompanyInventor: Jeff K. Curtis
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Patent number: 4803268Abstract: The present invention relates to a novel, optimized process for the preparation of cyclohexanedionecarboxylic acid derivatives of formula I which can be carried out in a single vessel affording a very good yield, which process comprises heating a reactive carboxylic acid derivative of formula III ##STR1## wherein X is a halide, an alkylsulfonic or arylsulfonic acid radical or the molecular radical ##STR2## which is necessary to form an anhydride and R.sub.1 is alkyl or cycloalkyl, with an alkali metal cyanide or copper cyanide, in an inert organic solvent, to give a mixture, then adding in succession to said mixture, at a temperature in the range from 0.degree. C.Type: GrantFiled: January 29, 1987Date of Patent: February 7, 1989Assignee: Ciba-Geigy CorporationInventors: Hans-Georg Brunner, Urs Muller
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Patent number: 4800203Abstract: There are described pyrrolo[1,2-b]cinnolines having the formula ##STR1## where R.sub.1 when present is hydrogen, loweralkyl, arylloweralkyl or --CH.sub.2 CO.sub.2 C.sub.2 H.sub.5 ; R.sub.2 is hydrogen, loweralkyl, arylloweralkyl, chlorine, bromine, iodine, formyl, nitro, --Ch.dbd.CR.sub.3 R.sub.4 or --CH.sub.2 CHR.sub.3 R.sub.4, R.sub.3 and R.sub.4 being independently hydrogen, loweralkyl, aryl or arylloweralkyl; X is oxygen, amino, loweralkylamino, arylloweralkylamino or methoxy; and Y is hydrogen, fluorine, chlorine, bromine, iodine, trifluoromethyl or nitro, and pharmaceutically acceptable acid addition salts thereof which are useful as analgesic agents and as enhancers of cholinergic function and hence for the treatment of memory dysfunctions and senile dementia's such as Alzheimer's disease characterized by diminished cholinergic function.Type: GrantFiled: September 24, 1987Date of Patent: January 24, 1989Assignee: Hoechst-Roussel Pharmaceuticals, Inc.Inventors: R. Russell Hamer, Richard C. Effland, Joseph T. Klein
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Patent number: 4798901Abstract: Novel pyrrole derivatives of the formula ##STR1## wherein one of R.sub.2 and R.sub.3 is ##STR2## and the other of R.sub.2 and R.sub.3 as well as R.sub.4 and R.sub.5 are individually selected from the group consisting of hydrogen, halogen, alkyl of 1 to 18 carbon atoms, aryl of 6 to 14 carbon atoms, aralkyl of 7 to 18 carbon atoms, --CN, --CF.sub.3, --NO.sub.2, --COOAlk and Alk is alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, ##STR3## n is 0, 1 or 2, R', R.sub.1 ' and R.sub.2 ' are alkyl of 1 to 8 carbon atoms and R.sub.4 and R.sub.5 taken together with the carbon atoms to which they are attached may form an optionally further unsaturated carbon homocycle of up to 8 carbon atoms, Z is selected from the group consisting of hydrogen, --CN, --C.tbd.CH, --CF.sub.3 and alkyl of 1 to 3 carbon atoms, A is the residue of a pyrethrinoid acid, R.sub.Type: GrantFiled: December 2, 1987Date of Patent: January 17, 1989Assignee: Roussel UclafInventors: Jean Tessier, Jean-Pierre Demoute, Laurent Taliani
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Patent number: 4797152Abstract: Novel cyclohexenonecarboxylic acid derivatives exhibit herbicidal and plant growth regulating activity.The cyclohexanedionecarboxylic derivatives are of the formula I ##STR1## wherein A is an aliphatic or aromatic alcohol, or is an amino group which may be substituted by halogen, lower alkoxy, lower alkylthio, nitro or cyano, or is a heterocyclic amino group which is unsubstituted or substituted,R is C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl, each unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio,R.sub.1 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl or C.sub.3 -C.sub.6 alkylnyl,B is an aliphatic or aromatic radical or is an aliphatic or aromatic carbonyl or sulfonyl group which may be substitued by halogen, lower alkoxy, lower alkylthio, nitro or cyano.The compounds are suitable for selectively controlling grasses in crops of useful plants.Type: GrantFiled: November 14, 1986Date of Patent: January 10, 1989Assignee: Ciba-Geigy CorporationInventor: Hans-Georg Brunner
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Patent number: 4760061Abstract: Mono- or bis-complex esters or ethers of a phenol derivative of the formulaNU--A--X--R.sup.1wherein NU is a defined mono- or bis-phenolic nucleus including a hydroxyphenyl-hydroxynaphthyl; hydroxyphenyl-hydroxyindanyl, hydroxyphenyl-hydroxybenzothienyl or di-hydroxyphenyl-ethylene or vinylene nucleus; whereinA is alkylene, alkenylene or alkynylene which may be interrupted by phenylene or other linkages, whereinR.sup.1 is hydrogen, or alkyl, alkenyl, cycloalkyl, halogenoalkyl, aryl or arylalkyl, or R.sup.1 is joined to R.sup.2, and wherein X is --CONR.sup.2 --, --CSNR.sup.2 --, --NR.sup.12 CO--, --NR.sup.12 CS--, --NR.sup.12 CONR.sup.2 --, ##STR1## --SO.sub.2 NR.sup.2 -- or --CO--, or, when R.sup.1 is not hydrogen, is --NR.sup.12 COO--, --S--, --SO-- or --SO.sub.2 --, whereinR.sup.2 is hydrogen or alkyl, or R.sup.1 and R.sup.2 together form alkylene; whereinR.sup.12 is hydrogen or alkyl, and whereinR.sup.22 is hydrogen, cyano or nitro; or a salt thereof when appropriate.Type: GrantFiled: April 24, 1985Date of Patent: July 26, 1988Assignee: Imperial Chemical Industries PLCInventors: Philip N. Edwards, Brian S. Tait