Nitrogen Or Chalcogen Attached Indirectly To The Hetero Ring By Nonionic Bonding Patents (Class 549/72)
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Patent number: 5334730Abstract: The present invention provides a process for the preparation of optically active carboxylic acids of the formula I* or II* ##STR1## in which X is an oxygen or sulfur atom and n is 1 or 2. The process comprises reacting a racemic carboxylic acid I or II or its derivatives with an optically active 2-amino-carboxylic acid ester to give the diastereomeric carboxylic acid amides, separating the diastereomers and, after cleavage of the amide bond, isolating the optically active carboxylic acids of the general formula I* or II*. The invention also provides certain novel optically active carboxylic acid amides and a tetrahydrothiopyran-2-carboxylic acid.Type: GrantFiled: July 1, 1992Date of Patent: August 2, 1994Assignee: Consortium fur Elektrochemische Industrie GmbHInventor: Elke Fritz-Langhals
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Patent number: 5312831Abstract: The invention relates to novel ureas and urethanes of Formula I: ##STR1## which stimulate cytokine production and may be used to accelerate recovery from neutropenia accompanying radio- or chemotherapy, bone marrow transplantation, or infections. Compounds in the invention or pharmaceutical compositions employing these compounds may be useful in the treatment of cancer, AIDS, aplastic anemia, myelodysplastic syndrome, and infectious diseases, and in the enhancement of immune response.Type: GrantFiled: May 12, 1993Date of Patent: May 17, 1994Assignee: American Cyanamid CompanyInventors: Semiramis Ayral-Kaloustian, Steven R. Schow, Mila T. Du, James J. Gibbons, Jr.
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Patent number: 5290952Abstract: The novel compounds of formula ##STR1## wherein n and R are as defined in claim 1, are very suitable for use as UV absorbers in layers of photographic materials.Type: GrantFiled: June 30, 1992Date of Patent: March 1, 1994Assignee: Ciba-Geigy CorporationInventors: David G. Leppard, Kurt Burdeska
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Patent number: 5278311Abstract: Novel nonionic contrast agents of the formula ##STR1## or dimers of the formula ##STR2## are disclosed where X, Z and R.sub.1 -R.sub.5 are as defined herein.Type: GrantFiled: June 5, 1992Date of Patent: January 11, 1994Assignee: E. R. Squibb & Sons, Inc.Inventors: Thangavel Arunachalam, Ramachandran Ranganathan
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Patent number: 5278333Abstract: A process for the .alpha.-monoalkylation of arylacetonitriles, arylacetoesters and arylacetic acids with dialkyl carbonates in liquid phase, in the presence of bases at temperatures ranging from about 100.degree. C. to about 270.degree. C.Type: GrantFiled: July 30, 1992Date of Patent: January 11, 1994Assignee: Tessenderlo Chemie N.V.Inventors: Pierre C. Loosen, Pietro Tundo, Maurizio Selva
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Patent number: 5242940Abstract: N-1 and C-5 heterocyclic pyrazoles, a method of their preparation, compositions containing the same and methods of their use are disclosed. The pyrazoles are useful in alleviating inflammatory and cardiovascular disorders in mammals.Type: GrantFiled: December 17, 1991Date of Patent: September 7, 1993Assignee: Ortho Pharmaceutical CorporationInventors: Michael P. Wachter, William V. Murray
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Patent number: 5234946Abstract: The substituted alkylamine derivatives represented by formula (I) ##STR1## wherein R.sup.1 represents (a) substituted or unsubstituted C.sub.2-6 alkenyl group, (b) substituted or unsubstituted C.sub.3-6 cycloalkenyl group, (c) substituted or unsubstituted C.sub.2-6 alkynyl group, (d) substituted or unsubstituted aryl group, (e) substituted or unsubstituted heterocyclic group, (f) fused heterocyclic group which may be substituted, or (g) group represented by the formula Ru.sup.11 -Ar wherein R.sup.11 is a heterocyclic group and Ar is a 5- or 6-membered aromatic ring which may contain a hetero N, O or S atom, and which may be substituted; ##STR2## represents a 5- or 6-membered aromatic ring which may contain a hetero N, O or S atom, and may be substituted by R.sup.7,X and Y are linking groups,R.sup.2 is H or lower alkyl,R.sup.3 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl or lower cycloalkyl,R.sup.4 and R.sup.5 are independently hydrogen or halogen atoms,R.sup.Type: GrantFiled: August 30, 1991Date of Patent: August 10, 1993Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Hiroshi Takezawa, Masahiro Hayashi, Yoshikazu Iwasawa, Masaaki Hosoi, Yoshiaki Iida, Yoshimi Tsuchiya, Masahiro Horie, Toshio Kamei
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Patent number: 5235068Abstract: Acylaromatic compounds ##STR1## (Q: aromatic compound residue; R: straight, branched or cyclic aliphatic group, aromatic group or araliphatic group) are prepared in high yield by a reaction, in the presence of a boron trifluoride complex catalyst, of an aromatic compound with ##STR2## (X: H, Cl, Br; Y: Cl, Br) or with RCOOH in the presence of (XYCHCO).sub.2 O.Type: GrantFiled: July 21, 1992Date of Patent: August 10, 1993Assignee: Sumitomo Chemical Company, LimitedInventors: Masayoshi Minai, Michitada Kondo, Yuji Ueda, Seiichi Kai, Takayuki Higashii
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Patent number: 5225545Abstract: The compounds of the formula (1) indicated in claim 1 are suitable for use as direct dyes for dyeing and printing a wide range of materials, in particular cellulose-containing fibre materials, producing dyeings and prints having good fastness properties.Type: GrantFiled: May 12, 1992Date of Patent: July 6, 1993Assignee: Ciba-Geigy CorporationInventor: Urs Lauk
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Patent number: 5206389Abstract: These acrylates are those of formulae: ##STR1## where R=C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.12 cycloalkyl, aryl, arylalkyl or alkylaryl; Y=C.sub.1 -C.sub.12 alkyl, C.sub.6 -C.sub.12 aryl, heterocyclic radical whose ring contains from 5 to 10 members and whose heteroatom is chosen from N, O and S, an alkylaryl in which the alkyl part contains from 1 to 4 carbon atoms, Y not being able to denote 1,4-phenylene when R denotes methyl; and Z=hydrocarbon radical containing at least 2 C forming with O and the 2 adjacent Cs a ring containing from 4 to 8 members.To prepare them, an acrylate of formula CH.sub.2 .dbd.CH--COOR is reacted with a dialdehyde OHC--Y--CHO in the presence of an effective quantity of at least one functionalisation catalyst.The invention also relates to the preparation of new polymers and copolymers from the said acrylates.Type: GrantFiled: June 27, 1991Date of Patent: April 27, 1993Assignee: AtochemInventors: Marie-Christine Berthe, Paul Caubere, Yves Fort
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Patent number: 5201934Abstract: Carboxamides of the formulae Ia to Ic ##STR1## where X is oxygen or sulfur;R.sup.1 is hydrogen or substituted or unsubstituted cycloalkyl or alkyl;R.sup.2 is hydroxy, alkoxy, cyanoalkyl, substituted or unsubstituted alkenyl, alkynyl, phenyl or naphthyl, or one of the groups stated for R.sup.1 ;R.sup.3 and R.sup.4 are nitro, cyano, halogen, substituted or unsubstituted amino, alkoxy, alkylthio, substituted or unsubstituted alkenyl, alkynyl, phenyl, phenoxy or phenylthio, or one of the groups stated for R.sup.1 ;R.sup.5 is formyl, 4,5-dihydrooxazol-2-yl or COYR.sup.6 (Y.dbd.O,S);R.sup.6 is hydrogen, cycloalkyl, substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkenyl or phenyl,phthalimido, tetrahydrophthalimido, succinimido, maleimido, benzotriazolyl ora group --N.dbd.CR.sup.7 R.sup.8, whereR.sup.7 and R.sup.8 are hydrogen or alkyl, and R.sup.8 may also be cycloalkyl, phenyl, or R.sup.7 and R.sup.8 together form a 4- to 7-membered alkylene chain;and if R.sup.Type: GrantFiled: October 3, 1990Date of Patent: April 13, 1993Assignee: BASF AktiengesellschaftInventors: Peter Muenster, Gerd Steiner, Wolfgang Freund, Bruno Wuerzer, Karl-Otto Westphalen
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Patent number: 5194614Abstract: Compounds of general formula: ##STR1## in which A and R are defined in the description.Type: GrantFiled: February 26, 1991Date of Patent: March 16, 1993Assignee: Adir et CompagnieInventors: Jean Andrieux, Raymond Houssin, Said Yous, Beatrice Guardiola, Daniel Lesieur
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Patent number: 5192765Abstract: Amines of the following formula: ##STR1## where the variables are defined in the specification are useful in the treatment of diseases associated with altered motility and/or tone of smooth muscle.Type: GrantFiled: June 6, 1991Date of Patent: March 9, 1993Assignee: Pfizer Inc.Inventors: David Alker, Robert J. Bass, Peter E. Cross
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Patent number: 5190573Abstract: Cyclohexenone oxime ethers ##STR1## where R.sup.1 is alkyl;A is substituted or unsubstituted alkylene or alkenylene, where methylene is replaced by an oxygen atom, a sulfur atom, a sulfoxyl group, a sulfonyl group or --NR.sup.a --,Z is phenyl or a 5- or 6-membered heteroaromatic structure;X is substituted or unsubstituted amino, nitro, cyano, halogen, 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 -haloalkoxy, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, substituted or unsubstituted benzyloxycarbony or phenyl;n is 0 to 3, or 1 to 5 where X is halogen;R.sup.Type: GrantFiled: May 8, 1991Date of Patent: March 2, 1993Assignee: BASF AktiengesellschaftInventors: Ulf Misslitz, Norbert Meyer, Juergen Kast, Norbert Goetz, Albrecht Harreus, Bruno Wuerzer, Helmut Walter, Karl-Otto Westphalen, Matthias Gerber
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Patent number: 5183818Abstract: The present invention provides compounds having the structureY-Het-[Q.sub.1 ]-X-[Q.sub.2 ]-Zwhich inhibit the catalytic action of lipoxygenase enzymes, particularly 5-lipoxygenase, and thereby reduce the biosynthesis of leukotrienes B.sub.4, C.sub.4, D.sub.4, and E.sub.4.In the generic formula given above, X is oxygen or sulfur and Het is a heteroaryl group selected from the group consisting of furyl, thienyl, 2-, 3-, and 4-pyridyl, 2- and 3-benzo[b]furyl, 2- and 3-benzo[b]thienyl and thienothienyl.Y is one or two substituents independently selected from hydrogen, hydroxy, halogen, cyano, alkyl, haloalkyl, alkoxy, alkylthio, alkoxyaryl), alkylthioaryl, arylalkoxy, arylalkylthio, aryloxy, arylthio, alkylamido, cycloalkyl, alkanoyl, alkoxycarbonyl, amino, alkylamino, dialkylamino, and the following groups wherein R, at each occurrence, is independently selected from hydrogen and alkyl of from one to six carbon atoms: --CRROR, --NRC(O)R, --NRC(O)OR, and --C(O)NRR.The group Q.sub.Type: GrantFiled: August 27, 1991Date of Patent: February 2, 1993Assignee: Abbott LaboratoriesInventors: Dee W. Brooks, Andrew O. Stewart, Jonathan G. Martin
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Patent number: 5175183Abstract: Certain N-aryl, N-heteroaryl-, N-arylalkyl-, N-heteroarylalkyl-, N-arylcyclopropyl- and N-heteroaryl-cyclopropyl-N'-hydroxyurea compounds are inhibitors of lipoxygenase enzyme activity and are thus useful agents in treating disease states such as asthma, arthritis, allergy, psoriasis, inflammatory bowel disease, gout, adult respiratory distress syndrome, endotoxin shock, and other inflammatory conditions in which the products of the arachidonic acid cascade are implicated.Type: GrantFiled: July 10, 1991Date of Patent: December 29, 1992Assignee: Abbott LaboratoriesInventors: Dee W. Brooks, James B. Summers, Karen E. Rodriques
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Patent number: 5175185Abstract: Retinoid like activity is exhibited by compounds of the formula ##STR1## R.sub.1 -R.sub.3 independently are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, A and A.sub.1 independently are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, SR.sub.4 or OR.sub.4 where R.sub.4 is lower alkyl, cycloalkyl or lower alkenyl; Y is selected from a group consisting of thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl or oxazolyl; E is lower alkenyl, lower alkynyl, lower cycloalkyl, lower branched chain alkyl, or is characterized by the formula (CH.sub.2).sub.n where n is 0-5, and Z is H, OH, OR.sub.5, OCOR.sub.5, --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH.sub.2 OH, CH.sub.2 OR.sub.6, CH.sub.2 OCOR.sub.6, or --CHO, CH(OR.sub.7).sub.2, CHOR.sub.8 O, or COR.sub.9, CR.sub.9 (OR.sub.7).sub.2, CR.sub.9 OR.sub.8 O where R.sub.5 is lower alkyl, phenyl or lower alkylphenyl, R.sub.6 is lower alkyl, phenyl or lower alkylphenyl, R.sub.7 is lower alkyl, R.sub.Type: GrantFiled: March 14, 1991Date of Patent: December 29, 1992Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna
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Patent number: 5166161Abstract: 3-Oxo-4-acyl or carbamyl-bicyclic aromatic and heterocyclic compounds as inhibitors of cyclooxygenase and lipoxygenase and useful as antiallergy and antiinflammatory agents.Type: GrantFiled: January 22, 1991Date of Patent: November 24, 1992Assignee: Pfizer Inc.Inventors: Toshihide Kokura, Kazunari Nakao, Fumitaka Ito, Masami Nakane
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Patent number: 5166218Abstract: Tertiary and secondary amines of the formulas ##STR1## and ##STR2## wherein n is the integer 1 or 2,R is hydrogen, lower-alkanoyl or phenyl-lower-alkanoyl,X.sup.1 is phenoxymethyl optionally mono-fluorinated or mono-chlorinated in the ortho-position,X.sup.2 is lower-alkyl, phenoxymethyl optionally mono-fluorinated or mono-chlorinated in the ortho-position or phenyl optionally monosubstituted by fluorine, chlorine, trifluoromethyl or lower-alkoxy,Y is hydrogen or methyl, andZ is a phenyl or thienyl residue substituted as hereinafter described,and the physiologically and pharmaceutically compatible salts are described. The compounds of formulas I and V-1 have catabolic activity and can be used for the treatment of obesity and diabetes mellitus or for the treatment of conditions which are associated with an increased protein breakdown, or as feed additives for fattening animals. The compounds of formulas I and V-1 can be prepared starting from corresponding primary amines.Type: GrantFiled: August 12, 1991Date of Patent: November 24, 1992Assignee: Hoffmann-La Roche Inc.Inventors: Leo Alig, Marcel Muller
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Patent number: 5149705Abstract: Retinoid-like activity is exhibited by compounds of the formula ##STR1## where R is hydrogen or lower alkyl; A is pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 0-5; and B is H, --COOH or an ester or amide thereof, --CH.sub.2 OH or an ether or ester derivative thereof, or --CHO or an acetal derivative thereof, or --COR.sub.1 or a ketal derivative thereof where R.sub.1 is --(CH.sub.2).sub.m CH.sub.3 where m is 0-4; or a pharmaceutically acceptable salt thereof.Type: GrantFiled: March 13, 1987Date of Patent: September 22, 1992Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna
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Patent number: 5131945Abstract: Compounds of formula I ##STR1## are useful as herbicides, effective against dicotyledonous weeds.Type: GrantFiled: July 13, 1990Date of Patent: July 21, 1992Assignee: Shell Research LimitedInventors: Hans-Joachim Bissinger, Ludwig Schoeder, Helmut Baltruschat, Manfred Garrecht, Erich Raddatz, Wolfgang Fruhstorfer
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Patent number: 5122611Abstract: A method for producing an azomethine or indoaniline series dye, which comprises oxidatively condensing an active methylene- or methine-containing compound, except those containing a sulfonic or carboxylic acid group, and p-phenylenediamine, except those containing a sulfonic or carboxylic acid group, in the presence of methylene chloride as a solvent under a basic condition.Type: GrantFiled: August 23, 1990Date of Patent: June 16, 1992Assignee: Fuji Photo Film Co., Ltd.Inventors: Mitsugu Tanaka, Hisashi Mikoshiba
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Patent number: 5117057Abstract: This invention relates to insecticidal compositions containing N'-substituted-N,N'-disubstitutedhydrazines, methods of using such compositions and N'-substituted-N, N'-disubstitutedhydrazines. Specifically, the invention relates to insect growth regulating compositions, and methods of using such compositions, which include compounds having a nucleus of the formula ##STR1## where A', B', D and J are independently any atom or group of atoms; where E is a tertiary carbon containing organic radical, a haloalkyl having a total of at least four carbon and halogen atoms but not more than six halogen atoms, or a non-tertiary carbon containing non-haloalkyl organic or organometallic radical having at least five atoms other than hydrogen, oxygen and halogen, and is attached to the nitrogen shown in the formula by a carbon-to-nitrogen single bond; where one G.sub.1 is C, N, O and S, and both G.sub.2 's and the other G.sub.1 are carbon; or one G.sub.2 is S or P, and both G.sub.1 's and the other G.sub.Type: GrantFiled: June 14, 1991Date of Patent: May 26, 1992Assignee: Rohm and Haas CompanyInventors: Adam C. Hsu, Harold E. Aller, Raymond A. Murphy, Dat P. Le, Donald W. Hamp, Barry Weinstein
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Patent number: 5116954Abstract: Substituted six-membered benzo-fused heterocycles of the formula (I) ##STR1## in which: X=0, NH, S.fwdarw.(O).sub.n (n=0 or 2);R.sub.1 is phenyl, phenyl substituted by methoxy, hydroxy, chlorine, fluorine, diethylaminoethoxy, phenoxy, 2-methyl-4-thiazolyl, 2-amino-4-thiazolyl, phenyl, amino, nitro, terbutyl, carboxymethyl, acetamido, dimethyltriazenyl, benzoyl, hexyl, undecyl, trifluoromethyl, carbamoyl; or R.sub.1 is trifluoromethyl, pyridyl-2,pyridyl-4;R.sub.2 is H, methoxy, hydroxy; orR.sub.1 and R.sub.2 are --CH.dbd.CH--CH.dbd.CH--;R.sub.3 and R.sub.4 are methoxy, hydroxy, fluorine or form a fused benzene ring;CR.sub.5 R.sub.6 R.sub.7 is carboxymethyl, --CH.sub.2 --PO.sub.3 H,--CH.sub.2 --PO(oET).sub.2, 4-methylpiperazinyl, aminomethyl,3-4-5-trimethoxyphenylaminomethyl, acetyl, bromoacetyl, hydroxyethyl, acetoxyethyl, mercaptomethyl, acetylthiomethyl, methoxy-carbopnylthiomethyl, --CH--CONH.sub.2, ##STR2## substituted thiazolyl, subsituted furanone, imidazo(1,2-a)pyridinyl, indolizinyl, or R.sub.4 and R.Type: GrantFiled: August 2, 1989Date of Patent: May 26, 1992Assignee: Lipha, Lyonnaise Industrielle PharmaceutiqueInventors: Philippe Briet, Jean-Jacques Berthelon, Francois Collonges
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Patent number: 5073184Abstract: Compounds of formula (I): ##STR1## and stereoisomers thereof, wherein W is R.sup.1 O.sub.2 C--C.dbd.CH--ZR.sup.2, wherein R.sup.1 and R.sup.2, which are the same or different, are alkyl or fluoroalkyl groups, and Z is either an oxygen or sulphur atom; A is an oxygen or sulphur atom, --NR.sup.3 --, or --CR.sup.4 R.sup.5 --; X, Y and Z.sup.Type: GrantFiled: April 9, 1990Date of Patent: December 17, 1991Assignee: Imperial Chemical Industries PLCInventors: Vivienne M. Anthony, John M. Clough, Paul deFraine, Christopher R. A. Godfrey, Kevin Beautement
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Patent number: 5064827Abstract: Compounds of the present invention, are represented by the general formula ##STR1## wherein R.sub.1 group which may be alkyl of from 1 to about 6 carbon atoms, alkenyl of from 2 to about 6 carbon atoms, alkynyl of from 2 to about 10 carbon atoms, alkoxy wherein the alkyl group contains from 1 to about 6 carbon atoms, halogen, acetamido, amino, nitro, alkylamino of from 1 to about 6 carbon atoms, hydroxy, hydroxyalkyl of from 1 to about 6 carbon atoms, cyano or arylalkoxy wherein the alkyl group contains from 1 to about 6 carbon atoms R.sub.2, R.sub.3 and R.sub.4 are hydrogen or hydroxyl groups or the combination of either hydrogen or hydroxyl groups; W represents alkylene of from 1 to about 10 carbon atoms; and B represents --NHCOR.sub.5, --NHCONR.sub.5 R.sub.6, or --NHCOOR.sub.5 wherein R.sub.5 and R.sub.Type: GrantFiled: August 23, 1990Date of Patent: November 12, 1991Assignee: Du Pont Merck Pharmaceutical CompanyInventors: Ghanshyam Patil, William L. Matier, Khuong H. X. Mai
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Patent number: 5064863Abstract: Tertiary and secondary amines of the formulas ##STR1## wherein n is the integer 1 or 2, p0 R is hydrogen, lower-alkanoyl or phenyl-lower-alkanoyl,X.sup.1 is phenoxymethyl optionally mono-fluorinated or mono-chlorinated in the ortho-position,X.sup.2 is lower-alkyl, phenoxymethyl optionally mono-fluorinated or mono-chlorinated in the ortho-position or phenyl optionally monosubstituted by fluorine, chlorine, trifluoromethyl or lower-alkoxy,Y is hydrogen or methyl, andZ is a phenyl or thienyl residue substituted as hereinafter described,and the physiologically and pharmaceutically compatible salts are described. The compounds of formulas I and V-1 have catabolic activity and can be used for the treatment of obesity and diabetes mellitus or for the treatment of conditions which are associated with an increased protein breakdown, or as feed additives for fattening animals. The compounds of formulas I and V-1 can be prepared starting from corresponding primary amines.Type: GrantFiled: December 10, 1987Date of Patent: November 12, 1991Assignee: Hoffmann-La Roche Inc.Inventors: Leo Alig, Marcel Muller
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Patent number: 5055471Abstract: This invention relates to derivatives of propanoic acid of the formula ##STR1## Useful as fungicides, insecticides and miticides, to processes for preparing them, to compositions containing them, and to methods of using them to combat fungi, especially fungal infections of plants, and to kill or control insects and mites.Type: GrantFiled: November 15, 1989Date of Patent: October 8, 1991Assignee: Imperial Chemical Industries PLCInventors: Paul J. de Fraine, Anne Martin
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Patent number: 5053504Abstract: A process is disclosed for providing benzazepine intermediates of the formulae ##STR1## wherein R.sub.3, R.sub.4 and Y are as defined herein, which intermediates are useful in a process for the preparation of pharmaceutically useful benzazepine derivatives.Type: GrantFiled: November 29, 1989Date of Patent: October 1, 1991Assignee: E. R. Squibb & Sons, Inc.Inventors: Wen-Sen Li, John K. Thottathil, Michael Murphy
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Patent number: 5047555Abstract: There are disclosed a 4-aminophenol derivative of the formula: ##STR1## (wherein R.sup.1 and R.sup.2 each represent a lower alkyl group, Y represents a single bonding arm, a lower alkylene group or a lower alkenylene group, R.sup.3 represents a thienyl group or pyrrolyl group which may be also substituted with a lower alkyl group; benzothienyl group, indolyl group; or a phenol group which is substituted with 1 to 2 groups selected from a lower alkoxy group and a lower alkanoyloxy group; or Y-R.sup.3 represents integrally an alkyl group with 6 to 9 carbon atoms; or a hydrocarbon group with 5 to 14 carbon atoms having 2 or 3 double bonds) or a pharmacologically acceptable salt thereof, and processes for preparing the same.Type: GrantFiled: December 4, 1989Date of Patent: September 10, 1991Assignee: Tanabe Seiyaku Co., Ltd.Inventors: Hirozumi Inoue, Kei Tsuzurahara, Katsuo Ikezawa, Tomofumi Uchida
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Patent number: 5034049Abstract: Thiophene-2-carboxylic acid derivatives of the general formula I ##STR1## where R.sup.1 to R.sup.3 are each hydrogen, halogen, branched or straight-chain C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.8 -alkoxy, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -haloalkoxy, nitro, cyano, unsubstituted phenyl or phenyl which is mono- to trisubstituted by C.sub.1 -C.sub.4 -alkyl, halogen, C.sub.1 -C.sub.5 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.5 -haloalkoxy;X is --OR.sup.4 or --NH--OR.sup.5,R.sup.4 being branched or straight-chain C.sub.3 -C.sub.10 -alkynylalkyl which is unsubstituted or substituted by halogen; andR.sup.5 being branched or straight-chain C.sub.1 -C.sub.5 -alkyl which is unsubstituted or substituted by halogen, or branched or straight-chain C.sub.3 -C.sub.10 -alkynylalkyl which is unsubstituted or substituted by halogen;with the proviso that R.sup.4 is not propargyl when R.sup.2 and R.sup.3 are both hydrogen or when R.sup.2 is halogen or R.sup.3 is chlorine, methyl or methoxy.Type: GrantFiled: January 9, 1990Date of Patent: July 23, 1991Assignee: BASF AktiengesellschaftInventors: Reiner Kober, Rainer Seele, Hans-Juergen Neubauer, Thomas Saupe, Bruno Wuerzer, Norbert Meyer, Karl-Otto Westphalen
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Patent number: 5032609Abstract: The invention relates to compounds of general formula (I) and physiologically acceptable salts and solvates thereof, methods for their preparation and pharmaceutical formulations thereof. ##STR1## wherein Ar represents a substituted phenyl or nitrogen-containing heterocyclic ring;X and Y represent alkylene, alkenylene or alkynylene chains;R.sup.1, R.sup.2 and R.sup.18 each represent hydrogen or alkyl groups; andQ represents an optionally substituted furan or thiophene ring.The compounds of the invention have a stimulant action at .beta..sub.2 -adrenoreceptors and are useful in the treatment of diseases associated with reversible airways obstruction such as asthma and chronic bronchitis.Type: GrantFiled: December 16, 1988Date of Patent: July 16, 1991Assignee: Glaxo Group LimitedInventors: Ian F. Skidmore, Harry Finch, Alan Naylor, Lawrence H. C. Lunts, Charles Willbe, David Middlemiss
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Patent number: 5030654Abstract: A series of novel spiro-substituted glutaramide derivatives have been prepared, including the pharmaceutically acceptable salts thereof and bioprecursors therefor, wherein the spiro-substituent completes a 5- or 6-membered carbocycyclic ring and is located at the carbon atom adjacent to the carbamoyl group. These particular compounds are inhibitors of the neutral endopeptidase E.C.3.4.24.11 enzyme and are therefore useful in therapy as diuretic agents for the treatment of hypertension, heart failure, renal insufficiency and other disorders. Methods for preparing these compounds from known starting materials are provided.Type: GrantFiled: May 19, 1989Date of Patent: July 9, 1991Assignee: Pfizer Inc.Inventors: Ian T. Barnish, John C. Danilewicz, Keith James, Gillian M. R. Samuels, Nicholas K. Terrett, Michael T. Williams, Martin J. Wythes
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Patent number: 5030647Abstract: Novel thienylbenzylamine compounds of the formula ##STR1## wherein A and R.sub.1 -R.sub.5 are defined herein. These compounds are useful for the treatment of inflammation.Type: GrantFiled: February 9, 1990Date of Patent: July 9, 1991Assignee: Boehringer Ingelheim Pharmaceuticals, Inc.Inventors: Clara K. Miao, Karl G. Grozinger, Robert Rothlein, Ronald Faanes, Genus Possanza, John P. Devlin
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Patent number: 5013751Abstract: Disclosed are esters and amides of (+) suprofen, substantially free of the corresponding enantiomorp, (-) suprofen, having enhanced delivery characteristics on topical administration to the eye; also disclosed are pharmaceutical compositions comprising such (+) suprofen derivatives and methods of using them when indicated to achieve an anti-inflammatory effect on topical delivery to the eye.Type: GrantFiled: August 27, 1990Date of Patent: May 7, 1991Assignee: Alcon Laboratories, Inc.Inventors: Steven H. Gerson, Wesley W. Han
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Patent number: 5010104Abstract: Novel tricyclic compounds having a TXA.sub.2 -antagonizing activity represented by formul (I): ##STR1## which strongly antagonize an action of thromboxane A.sub.2 and are expected to have preventive and therapeutic effects on ischemica diseases, cerebro-vascular diseases, etc.Type: GrantFiled: June 29, 1989Date of Patent: April 23, 1991Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Etsuo Oshima, Hiroyuki Obase, Akira Karasawa, Kazuhiro Kubo, Ichiro Miki, Akio Ishii
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Patent number: 5001124Abstract: This invention is directed to compounds of the formula (I): ##STR1## wherein R.sup.1 is --OR.sup.4 (where R.sup.4 is hydrogen, lower alkyl, lower hydroxyalkyl, phenyl, phenyl-lower-alkyl, or --(CH.sub.2).sub.n Y where n is an integer from 1 to 4 and Y is morpholino, -SR.sup.5, --C(O)OR.sup.5, --C(O)N(R.sup.6).sub.2, --N(R.sup.6).sub.2, or --N.sup.+ (R.sup.6).sub.3 X.sup.-, in which R.sup.5 is lower alkyl, each R.sup.6 is independently selected from hydrogen or lower alkyl, and X is halogen)or --SR.sup.7 (where R.sup.7 is lower alkyl, phenyl-lower-alkyl, or --(CH.sub.2).sub.n W where W is --N(R.sup.6).sub.2 or --N.sup.+ (R.sup.6).sub.3 X.sup.-, and n, R.sup.6 and X are as previously defined);R.sup.2 is lower alkyl, phenyl or phenyl-lower-alkyl;R.sup.3 is halo, hydroxy, lower alkyl, lower alkoxy, lower haloalkyl, lower haloalkoxy, or --C(O)OR.sup.5 where R.sup.5 is as previously defined; andZ is a bond, 2,5-thienyl or 2,5-furanyl; or a pharmaceutically acceptable salt thereof.Type: GrantFiled: February 2, 1990Date of Patent: March 19, 1991Assignee: Syntex (U.S.A.) Inc.Inventors: John W. Patterson, Bruce H. Devens
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Patent number: 4999042Abstract: Compounds of the fomrula (I): ##STR1## and sterioisomers thereof, wherein X is halogen, alkyl, cycloalkyl, aralkyl, aryloxyalkyl, alkenyl, alkynyl, aryl, amino, arylazo, heteroarylalkyl, heteroaryloxyalkyl, acylamino nitro, nitride, trifluoromethyl, -OR.sup.1, -SR.sup.1, -CO.sub.2 R.sup.2, -CONR.sup.3 R.sup.4, -COR.sup.5, -CR.sup.6 .dbd.NR.sup.7, -N.dbd.CR8R.sup.9, -SOR.sup.10 or -SO.sub.2 R.sup.11 ; W, Y and Z, which may be the same or different, are any of the atoms or groups listed for X above and, in addition, may be hydrogen atoms; or any two of the groups W, X, Y and Z, in adjacent positions on the phenyl ring, optionally join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; R.sup.1 is alkyl, or cycloalkyl optionally containing a heteroatom in the cycloalkyl ring, alkenyl, acyl, aryl, heteroaryl, aralkyl or heteroarylalkyl; R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.8, R.sup.9, R.sup.10 and R.sup.Type: GrantFiled: December 19, 1989Date of Patent: March 12, 1991Assignee: Imperial Chemical Industries PLCInventors: Vivienne M. Anthony, John M. Clough, Christopher R. A. Godfrey, Thomas E. Wiggins
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Patent number: 4994615Abstract: Asymmetric hydrogenation of prochiral N-arylketimines to give optically active secondary amines at a temperature of -20.degree. to 80.degree. C., a hydrogen pressure of 10.sup.5 to 6.10.sup.6 Pa with the addition of catalytic amounts of an iridium compound of the formula III or IIIa[XIrYZ] (III)or[XIrY.sup..sym. A.sup..crclbar. (IIIa)in which X is two olefin ligands or one diene ligand, Y is a chiral diphosphine, the secondary phosphine groups of which are linked by 2-4 C atoms and which, together with the Ir atom, forms a 5-, or 6- or 7-ring, or Y is a chiral diphosphinite, the phosphinite groups of which are linked via 2 C atoms and which together with the Ir atom forms a 7-ring, Z is Cl, Br or I and A.sup.63 is the anion of an oxygen acid or complex acid, and if appropriate with the addition of an ammonium or alkali metal chloride, bromide or iodide.Type: GrantFiled: July 29, 1987Date of Patent: February 19, 1991Assignee: Ciba-Geigy CorporationInventors: Felix Spindler, Benoit Pugin
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Patent number: 4988728Abstract: Disclosed are esters and amides of suprofen having enhanced delivery characteristics on topical administration to the eye; also disclosed are pharmaceutical compositions comprising such suprofen derivatives and methods of using them when indicated to achieve an anti-inflammatory effect on topical delivery to the eye.Type: GrantFiled: July 23, 1990Date of Patent: January 29, 1991Assignee: Alcon Laboratories, Inc.Inventors: Steven H. Gerson, Wesley W. Han
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Patent number: 4980484Abstract: Retinoid-like activity is exhibited by compounds of the formula ##STR1## wherein A is pyridyl, furyl, thienyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 0-5; and B is H, --COOH and its esters, amides and pharmaceutically acceptable salts, --CHO and its acetal derivatives, --COR.sub.1 and its ketal derivatives where R.sub.1 is --(CH.sub.2).sub.n CH.sub.3 where n is defined above, or --CH.sub.2 OH and its ether and acyl ester derivatives; or a pharmaceutically acceptable salt.Type: GrantFiled: March 13, 1990Date of Patent: December 25, 1990Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna
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Patent number: 4980349Abstract: The invention relates to new compounds corresponding to formula I: ##STR1## in which: W represents C=O, CH.sub.2 or CHOH,Z represents ##STR2## R.sub.1 and R.sub.2 represent especially Cl or F, R, R' and R" represent especially H,X represents especially CH.sub.2,Y represents especially COOH,u and v are two integers ranging from 0 to 10,p and q take the value 0 or 1,n and m are two integers ranging 0 to 10 andt is 0 or 1the total number of carbon atoms in the chain ##STR3## ranging from 2 to 20, and to their physiologically acceptable salts obtained with organic or inorganic acids.These compounds are useful for preparing medicinal products which have, especially, anti-inflammatory properties.Type: GrantFiled: November 12, 1987Date of Patent: December 25, 1990Assignee: SANOFIInventors: Pierre Roger, Jean-Paul Fournier, Alain Martin, Jean Choay
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Patent number: 4970229Abstract: This invention relates to a compound of the formula: ##STR1## or a pharmaceutically acceptable salt thereof wherein X is oxygen, sulfur, or --CH.dbd.CH--;wherein Z is OR.sup.1 or --NR.sup.4 R.sup.5 ;wherein R.sup.1 is hydrogen, lower alkyl, or a pharmaceutically acceptable cation;wherein R.sup.2 is H, --CH.sub.3 or --C.sub.2 H.sub.5 ;wherein R.sup.3 is OH, H or .dbd.O;wherein R.sup.4 and R.sup.5 may independently be hydrogen, or lower alkyl having 1-6 carbon atoms, or R.sup.4 and R.sup.5 may act together with N to form a cyclic amide of the formula: ##STR2## wherein n is an integer from 4-5; and m is an integer from 0-4. More particularly, this invention relates to compounds of the above formula which have utility as LTB.sub.4 antagonists.Type: GrantFiled: August 7, 1989Date of Patent: November 13, 1990Assignee: G. D. Searle & Co.Inventors: Steven W. Djuric, Richard A. Haack, Stella S. Yu
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Patent number: 4970319Abstract: The invention relates to a process for the preparation of acyl isocyanates of formula ##STR1## in which R is an alkyl radical, a substituted or unsubstituted naphthyl or phenyl radical or a substituted or unsubstituted aromatic heterocyclic radical, which consists in reacting an acyl halide of formula ##STR2## in which R has the above meaning and X denotes a fluorine, chlorine or bromine atom, with a sodium or potassium cyanate in the presence of a compound chosen from tin(IV), zinc or nickel(II) halides.The acyl isocyanates thus prepared are very useful for forming ureas or carbamates.Type: GrantFiled: March 23, 1989Date of Patent: November 13, 1990Assignee: Societe Nationale des Poudres et ExplosifsInventors: Jean-Pierre Senet, Serge Lecolier, Paul Caubere, Deng Min-Zhi
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Patent number: 4959385Abstract: This invention relates to thioformamide derivatives of the formula: ##STR1## wherein R represents alkyl, Ar represents optionally substituted phenyl, Y represents an ethylene or methylene radical or a valency bond, and n represents 0 or 1, bioprecursors thereof and pharmaceutically acceptable salts thereof which possess useful pharmacological properties, processes for their preparation and compositions containing them.Type: GrantFiled: January 19, 1989Date of Patent: September 25, 1990Assignee: May & Baker LimitedInventors: David C. Cook, Terance W. Hart, Iain M. McLay, Malcolm N. Palfreyman, Roger J. Walsh, Jean-Claude Aloup
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Patent number: 4959390Abstract: Compounds of the present invention, are represented by the general formula ##STR1## wherein R.sub.1 group which may be alkyl of from 1 to about 6 carbon atoms, alkenyl of from 2 to about 6 carbon atoms, alkynyl of from 2 to about 10 carbon atoms, alkoxy wherein the alkyl group contains from 1 to about 6 carbon atoms, halogen, acetamido, amino, nitro, alkylamino of from 1 to about 6 carbon atoms, hydroxy, hydroxyalkyl of from 1 to about 6 carbon atoms, cyano or arylalkoxy wherein the alkyl group contains from 1 to about 6 carbon atoms R.sub.2, R.sub.3 and R.sub.4 are hydrogen or hydroxyl groups or the combination of either hydrogen or hydroxyl groups; W represents alkylene of from 1 to about 10 carbon atoms; and B represents --NHCOR.sub.5, --NHCONR.sub.5 R.sub.6, or --NHCOOR.sub.5 wherein R.sub.5 and R.sub.Type: GrantFiled: December 15, 1988Date of Patent: September 25, 1990Assignee: E. I. du Pont de Nemours and CompanyInventors: Ghanshyam Patil, William L. Matier, Khuong H. X. Mai
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Patent number: 4931581Abstract: A method and composition for the immunization of healthy useful plants against plant diseases containing as active ingredients compounds of formula ##STR1## in which: X is hydrogen, halogen, hydroxy, methyl, methoxy, HOOC or MOOC;Y is hydrogen, halogen, SO.sub.3 H, SO.sub.3 M, nitro, hydroxy or amino, M being the molar equivalent of an alkali metal or alkaline earth metal ion that is formed from a corresponding base or basic compound; andZ is cyano or --CO--A;A represents either --OH or --SH, the hydrogen atom of which may also be replaced by the molar equivalent of an inorganic or organic cationic residue,or wherein A represents any other organic residue which has a molecular weight of less than 900 and which may also contain one, or more than one, hetero atom, including the salts of the phytophysiologically tolerable 7-carboxylic acid or 7-thiocarboxylic acid with primary, secondary or tertiary amines or with inorganic bases.Type: GrantFiled: August 18, 1988Date of Patent: June 5, 1990Assignee: Ciba-Geigy CorporationInventors: Rolf Schurter, Walter Kunz, Robert Nyfeler
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Patent number: 4927947Abstract: Retinoid-like activity is exhibited by compounds of the formula ##STR1## wherein A is pyridyl, furyl, thienyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 0-5; and B is H, --COOH and its esters, amides and pharmaceutically acceptable salts, --CHO and its acetal derivatives, --COR.sub.1 and its ketal derivatives where R.sub.1 is --(CH.sub.2).sub.n CH.sub.3 where n is defined above, or --CH.sub.2 OH and its ether and acyl ester derivatives; or a pharmaceutically acceptable salt.Type: GrantFiled: January 30, 1989Date of Patent: May 22, 1990Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna
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Patent number: 4927835Abstract: Compounds of the formula (I): ##STR1## or a pharmaceutically acceptable salt thereof, wherein: R.sup.1 is cycloalkyl of 5 to 7 carbon atoms; aryl of 6 to 10 carbon atoms unsubstituted or substituted by straight or branched chain alkyl of 1 to 4 carbon atoms, halo or trifluoromethyl; or ##STR2## wherein A is oxygen, sulfur or NR.sup.5, wherein R.sup.5 is hydrogen, straight or branched chain alkyl of 1 to 4 carbon atoms or halo, and R.sup.6 is hydrogen, straight or branched chain alkyl of 1 to 4 carbon atoms or halo;R.sup.2 is straight or branched chain alkyl of 1 to 4 carbon atoms or cycloalkyl of 5 to 7 carbon atoms; andR.sup.3 and R.sup.4 are the same or different and each is hydrogen; straight or branched chain alkyl of 1 to 8 carbon atoms unsubstituted or substituted by hydroxy, acyloxy of 2 to 5 carbon atoms, carboxyl or carbamoyl;are useful for treating pain, inflammation and fever in humans and animals.Type: GrantFiled: March 1, 1989Date of Patent: May 22, 1990Assignee: Nippon Shinyaku Co., Ltd.Inventors: Masahiro Kise, Yoshihiko Yoshimoto, Hiroshi Fujisawa, Yasuo Sasaki, Shoji Yasufuku
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Patent number: 4923884Abstract: Retinoid-like activity is exhibited by compounds of the formula ##STR1## wherein A is pyridyl, furyl, thienyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 0-5; and B is H, --COOH and its esters, amides and pharmaceutically acceptable salts, --CHO and its acetal derivatives, --COR.sub.1 and its ketal derivatives where R.sub.1 is --(CH.sub.2).sub.n CH.sub.3 where n is defined above, or --CH.sub.2 OH and its ether and acyl ester derivatives; or a pharmaceutically acceptable salt.Type: GrantFiled: April 1, 1988Date of Patent: May 8, 1990Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna