Substituent On 5-position Contains Carbocyclic Ring Patents (Class 544/325)
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Patent number: 5783576Abstract: New compounds of general formula (I) are provided: ##STR1## which are explained in the specification can be prepared by a variety of methods. The compounds may be used in pharmaceutical compositions.Type: GrantFiled: August 9, 1996Date of Patent: July 21, 1998Assignee: Boehringer Ingelheim KGInventors: Otto Roos, Georg Speck, Walter Losel, Dietrich Arndts, Wolf-Dietrich Bechtel
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Patent number: 5773447Abstract: The present invention relates to tertiary 4-amino-2-ureidopyrimidine-5-carboxamides of formula I: ##STR1## in which R.sup.1 is (C.sub.1 -C.sub.8)-alkyl wherein one or more H are replaced by F; R.sup.2 is selected from the group consisting of F, Cl, Br, H, --O--(C.sub.1 -C.sub.8)-alkyl and (C.sub.1 -C.sub.8)-alkyl, wherein one or more of the H of the alkyls can be replaced by F; R.sup.3 is selected from the group consisting of F, Cl, Br, H, --O--(C.sub.1 -C.sub.4)-alkyl and (C.sub.1 -C.sub.4)-alkyl, wherein one or more of the H of the alkyl can be replaced by F; R.sup.4 is CF.sub.3 or OCF.sub.3 ; and their physiologically tolerable salts. Process for preparing the compounds of formula I are also described. The compounds are suitable for the treatment of disorders of lipid metabolism.Type: GrantFiled: June 13, 1997Date of Patent: June 30, 1998Assignee: Hoechst AktiengesellschaftInventors: Gerhard Rackur, Hans Georg Boger, Norbert Krass, Axel Hoffmann, Michael Leineweber
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Patent number: 5763450Abstract: Compounds of the formula: ##STR1## in which R.sup.1 is lower alkoxy, R.sup.2 is bromine or lower alkoxy, and R.sup.3 is aryl, heteroaryl or a group --Q--R.sup.30, wherein Q is ethylene, vinylene or ethynylene and R.sup.30 is aryl, heteroaryl, lower alkoxycarbonyl or carbamoyl;hydrolyzable esters of carboxylic acids of formula I; and pharmaceutically acceptable salts of these compounds are useful for treating infectious diseases.Type: GrantFiled: May 21, 1997Date of Patent: June 9, 1998Assignee: Hoffmann-La Roche Inc.Inventors: Philippe Guerry, Synese Jolidon, Raffaello Masciadri, Henri Stalder, Rudolf Then
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Patent number: 5747476Abstract: The present invention relates to compositions and methods for treating equines, such as horses, afflicted with equine protozoal myeloencephalitis or EPM. The therapeutic compositions comprise a combination of pyrimethamine and a sulfonamide, preferably, sulfadiazine, in the absence of known therapeutic amounts of trimethoprim.Type: GrantFiled: July 17, 1996Date of Patent: May 5, 1998Assignee: Mortar & Pestle Veterinary Pharmacy, Inc.Inventors: Meri Charm Russell, Clara K. Fenger
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Patent number: 5739333Abstract: Novel sulfonamide derivatives of the formula ?I!: ##STR1## wherein Ring A and Ring B are substituted or unsubstituted monocyclic, bicyclic or tricyclic hydrocarbon, or substituted or unsubstituted heterocyclic group, Q is single bond, --O--, --S--, --SO--, --SO.sub.2 -- or --CH.sub.2 --, Y is --0--, --S-- or --NH--, Alk is lower alkylene or alkenylene, Z is --O-- or --NH --, R is substituted or unsubstituted aromatic heterocyclic or aryl, R.sup.1 is H, substituted or unsubstituted amino, substituted or unsubstituted lower alkyl, alkenyl, alkynyl, substituted or unsubstituted lower alkylthio, or alkoxy, or substituted or unsubstituted heterocyclic or aryl, or pharmaceutically acceptable salts thereof, which are useful in the prophylaxis or treatment of disorders associated with endothelin activities such as hypertension, pulmonary hypertension, renal hypertension, Raynaud disease, bronchial asthma, gastric ulcer, chronic heart failure, etc.Type: GrantFiled: May 9, 1996Date of Patent: April 14, 1998Assignee: Tanabe Seiyaku Co., Ltd.Inventors: Koichiro Yamada, Kosuke Yasuda, Kohei Kikkawa, Rikako Kohno
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Patent number: 5736550Abstract: Pyrimidine derivatives useful as a gastrointestinal prokinetic agent, represented by formula ##STR1## wherein X is O or NR.sup.5, Y is O, S or NR.sup.5 wherein R.sup.5 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group or the like;R.sup.1 and R.sup.2 may be the same or different and each is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group or the like;R.sup.3 is CN, or COOR.sup.6 wherein R.sup.6 is a C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.6 cycloalkyl group, an aryl group or the like;R.sup.4 is --SR.sup.7 or --NR.sup.8 R.sup.9 wherein R.sup.7 is a C.sub.1 -C.sub.6 alkyl group;R.sup.8 is a C.sub.1 -C.sub.6 alkyl group or the like;R.sup.9 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group or the like, or R.sup.8 and R.sup.9 may represent, together with the nitrogen atom to which they are attached, an N-substituted piperazine ring of formula (X) ##STR2## wherein R.sup.10 represents a C.sub.1 -C.sub.6 alkyl group or the like or a pharmacologically acceptable salt thereof.Type: GrantFiled: November 15, 1996Date of Patent: April 7, 1998Assignee: Nisshin Flour Milling Co., Ltd.Inventors: Haruhiko Kikuchi, Hiroaki Satoh, Ruta Fukutomi, Kohei Inomata, Masashi Suzuki, Koichiro Hagihara, Takeo Arai, Setsuko Mino, Haruko Eguchi
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Patent number: 5723473Abstract: A fungicidal compound of formula (I): ##STR1## wherein A is hydrogen, halogen, hydroxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.1-4 haloalkoxy, C.sub.1-4 alkylcarbonyl, C.sub.1-4 alkoxycarbonyl, phenoxy, nitro or cyano; and one of R.sup.1 and R.sup.2 is optionally substituted isoquinoline while the other is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, halogen or cyano.Type: GrantFiled: April 11, 1995Date of Patent: March 3, 1998Assignee: Zeneca LimitedInventor: Brian Leslie Pilkington
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Patent number: 5712393Abstract: The present invention provides a compound of formula (1) ##STR1## in which: R.sub.4 represents a hydrogen atom, a halogen atom or a nitro group;R.sub.6 represents a hydrogen atom or a straight or branched (C.sub.1 -C.sub.6) alkyl group;R.sub.7 represents a chlorine atom or a hydroxyl group; andZ represents: a phenyl group optionally substituted with one or more halogen atoms, straight or branched (C.sub.1 -C.sub.4)alkyl groups, straight or branched (C.sub.1 -C.sub.4)alkoxy groups, or trifluoromethyl, formyl, --CH.sub.2 OR, --CH.sub.2 OCOR, --CH.sub.2 CONRR', --CH.sub.2 ONCOR, --COOR, nitro, --NHR, --NRR' or --NHCOR groups, wherein R and R' are each, independently, a hydrogen atom or a (C.sub.1 -C.sub.7) alkyl group; a heterocyclic group optionally substituted as defined above for phenyl; or a cyclo(C.sub.5 -C.sub.8)alkyl group; additionally, when R.sub.Type: GrantFiled: November 24, 1995Date of Patent: January 27, 1998Assignee: SynthelaboInventors: Jean Michel Altenburger, Gilbert Lassalle
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Patent number: 5684005Abstract: A class of substituted phenylpyrimidine compounds are disclosed which are potent inhibitors of the excitatory amino acid, glutamate. Such compounds are useful in the treatment or prevention of a range of CNS disorders including cerebral ischaemic damage and epilepsy.Type: GrantFiled: June 6, 1995Date of Patent: November 4, 1997Assignee: Glaxo Wellcome Inc.Inventors: Alistair Ainslie Miller, Malcolm Stuart Nobbs, Richard Martin Hyde, Michael John Leach
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Patent number: 5677310Abstract: The present invention is concerned with compounds having the formula ##STR1## the pharmaceutically acceptable acid addition salts thereof, and the stereochemically isomeric forms thereof, wherein R.sup.1 is hydrogen or C.sub.1-6 alkyl; R.sup.2 is hydrogen or C.sub.1-6 alkyl; R.sup.3 is C.sub.1-6 alkyl, hydroxy, cyano, halo, C.sub.1-6 alkyloxy, aryloxy, arylmethoxy, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.1-6 alkyl-S-, C.sub.1-6 alkyl(S.dbd.O)--, C.sub.1-6 alkylcarbonyl; R.sup.4 is hydrogen, halo, hydroxy, C.sub.1-6 alkyl, or C.sub.1-6 alkyloxy; or R.sup.3 and R.sup.4 taken together form a bivalent radical; R.sup.5 and R.sup.6 each independently are hydrogen, halo, hydroxy, C.sub.1-6 alkyl, C.sub.1-6 alkyloxy, aryloxy or arylmethoxy; R.sup.7 is hydrogen; Alk.sup.1 is C.sub.2-5 alkanediyl; Alk.sup.2 is C.sub.2-15 alkanediyl; Q is a heterocyclic ring containing at least one nitrogen atom or a radical of formula ##STR2## Pharmaceutical compositions, preparations and use as a medicine are described.Type: GrantFiled: February 5, 1996Date of Patent: October 14, 1997Assignee: Janssen Pharmaceutica N.V.Inventors: Guy Rosalia Eugene Van Lommen, Marcel Frans Leopold De Bruyn, Piet Tom Bert Paul Wigerinck
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Patent number: 5633374Abstract: Pyrimidine-cyanoguanidine compounds of Formula I and its pharmaceutically acceptable acid addition salts ##STR1## wherein R.sub.1 is hydrogen or methyl;R.sub.2 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.5 cycloalkyl, C.sub.3 -C.sub.5, hydroxy methyl, cycloalkyl methoxy-C.sub.1 -C.sub.5 alkyl, or R.sub.1 and R.sub.2 are combined to form a C.sub.3 -C.sub.6 carbocyclic ring;R.sub.3 and R.sub.4 are each independently selected to be hydrogen, C.sub.1 -C.sub.4 alkyl, F, Cl, Br, I or CF.sub.3 ;R.sub.5 is hydrogen, F or Cl;R.sub.6 is hydrogen, --NH.sub.2, --NHCH.sub.3, --NHC.sub.2 H.sub.5, --NHCH(CH.sub.3) .sub.2, --N(CH.sub.3).sub.2, --N(C.sub.2 H.sub.5).sub.2, NH(CH.sub.2).sub.m --OC.sub.1 --C.sub.3 alkyl (where m is 2 or 3), --NHC(O)C.sub.1 -C.sub.3 alkyl, Cl or Br; and n is 0 or 1.The compounds of Formula I are potassium channel blockers useful in the treatment of cardiovascular disorders such as congestive heart failure and hypertension and as a diuretic.Type: GrantFiled: November 20, 1995Date of Patent: May 27, 1997Assignee: The Upjohn CompanyInventors: Stephen J. Humphrey, Kaushik D. Meisheri, James H. Ludens, Jackson B. Hester, Jr.
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Patent number: 5610300Abstract: Compounds of the formulae I and Ia and their racemates ##STR1## in which A is --CH.sub.2 -- or --CH.sub.2 CH.sub.2 --, R.sub.1 is hydrogen or a protective group, R.sub.2 is hydrogen or a protective group or a radical forming a phosphorus-containing nucleotide bridge group and B is a purine or pyrimidine radical or an analogue thereof, can be used as antiviral active ingredients or for the preparation of biologically active oligonucleotides.Type: GrantFiled: June 6, 1995Date of Patent: March 11, 1997Assignee: Ciba-Geigy CorporationInventors: Karl-Heinz Altmann, Ren e Imwinkelried, Albert Eschenmoser
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Patent number: 5597828Abstract: A class of substituted phenylpyrimidine compounds are disclosed which are potent inhibitors of the excitatory amino acid, glutamate. Such compounds are useful in the treatment or prevention of a range of CNS disorders including cerebral ischaemic damage and epilepsy.Type: GrantFiled: June 6, 1995Date of Patent: January 28, 1997Assignee: Glaxo Wellcome Inc.Inventors: Alistair A. Miller, Malcolm S. Nobbs, Richard M. Hyde, Michael J. Leach
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Patent number: 5591746Abstract: A class of substituted phenylpyrimidine compounds are disclosed which are potent inhibitors of the excitatory amino acid, glutamate. Such compounds are useful in the treatment or prevention of a range of CNS disorders including cerebral ischaemic damage and epilepsy.Type: GrantFiled: June 6, 1995Date of Patent: January 7, 1997Inventors: Alistair A. Miller, Malcolm S. Nobbs, Richard M. Hyde, Michael J. Leach
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Patent number: 5587380Abstract: A class of substituted phenylpyrimidine compounds are disclosed which are potent inhibitors of the excitatory amino acid, glutamate. Such compounds are useful in the treatment or prevention of a range of CNS disorders including cerebral ischaemic damage and epilepsy.Type: GrantFiled: June 6, 1995Date of Patent: December 24, 1996Assignee: Glaxo Wellcome Inc.Inventors: Alistair A. Miller, Malcolm S. Nobbs, Richard M. Hyde, Michael J. Leach
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Patent number: 5571816Abstract: Compounds of the formula I ##STR1## in which R.sup.1 to R.sup.6 have the stated meanings, and the readily water-soluble salts of these compounds, and a process for the preparation thereof are described. The compounds are suitable for the treatment of lipid metabolism disorders which are beneficially influenced by a stimulation of the hepatic LDL receptor.Also described are compounds of the formula II ##STR2## and the salts thereof.Type: GrantFiled: August 16, 1995Date of Patent: November 5, 1996Assignee: Hoechst AktiengesellschaftInventors: Klaus-Dieter Kampe, Ernold Granzer, Michael Leineweber, Gerhard Rackur, Hans G. B oger
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Patent number: 5525604Abstract: A 4-aminopyrimidine of the formula (I): ##STR1## wherein A is a bond, C1-4 alkylene or C1-4 oxyalkylene;Y is a bond, C1-4 alkylene, C1-4 alkyleneoxy, C1-4 alkoxyphenylene or phenyl(C1-4)alkylene;Z is a bond or vinylene;R1 is 4-15 membered heterocyclic ring containing one or two nitrogen atom;R2 is (i) 4-15 membered heterocyclic ring containing one or two nitrogen, one or two of oxygen or one sulfur atom,(ii) C4-15 carbocyclic ring,(iii) C1-4 alkoxy,(iv) hydroxy(C1-4 alkoxy) or(v) hydroxy;R3 is (i) 4-15 membered heterocyclic ring containing one or two nitrogen, one oxygen, one sulfur, or one nitrogen and one sulfur atom,(ii) C4-15 carbocyclic ring,(iii) formula:CH2.dbd.CH(X)--whereinX is halogen.(iv) hydrogen.l is 1 or 2.and some compounds are excluded.and acid addition salts thereof, salts thereof; have inhibitory effect on cGMP-PDE, or additionally on TXA2 synthetase.Type: GrantFiled: August 24, 1994Date of Patent: June 11, 1996Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Sung J. Lee, Yoshitaka Konishi, Orest T. Macina, Kigen Kondo, Dingwei T. Yu, Tamara A. Miskowski
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Patent number: 5525724Abstract: A process for the preparation of chloropyrimidines of the formula ##STR1## in which the substituents may be alkyl, cycloalkyl, aryl or radicals containing heteroatoms, but in which at least one of the substituents R.sup.1 to R.sup.4 must be Cl, which involves:reacting a hydroxy-pyrimidine or its tautomeric keto form with phosphoryl chloride in the presence of an amine or amine hydrochloride;recovering phosphoryl chloride after the reaction by adding phosphorus pentachloride and distilling the phosphoryl chloride; andseparating the chloropyrimidine from the amine hydrochloride by addition of a solvent which will dissolve the chloropyrimidine but not the amine hydrochloride and removing the amine hydrochloride.Type: GrantFiled: February 27, 1995Date of Patent: June 11, 1996Assignee: Huels AktiengesellschaftInventor: Artur Hunds
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Patent number: 5496946Abstract: There is provided an improved process for producing novel compounds represented by the general formula: ##STR1## wherein the ring A/ represents a pyrrole ring which may be hydrogenated; X represents an amino, hydroxyl or mercapto group; R.sup.1, R.sup.2 and R.sup.3 each, being the same as or different from the other, represents hydrogen or an alkyl, alkenyl or alkynyl group which may be substituted; R.sup.4 represents OR.sup.5 wherein R.sup.5 represents hydrogen or a hydrocarbon group which may be substituted or NHCH(COOR.sup.6)CH.sub.2 CH.sub.2 COOR.sup.7 wherein R.sup.6 and R.sup.7 each represents hydrogen or a hydrocarbon group which may be substituted; and n represents an integer of 1 to 4, or a salt thereof from compounds represented by the general formula: ##STR2## wherein X, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and n are the same as defined above; Y.sup.1 and Y.sup.2 each represents oxygen or sulfur atom; R.sup.8 and R.sup.Type: GrantFiled: June 9, 1994Date of Patent: March 5, 1996Assignee: Takeda Chemical Industries, Ltd.Inventors: Hiroshi Akimoto, Takenori Hitaka, Tetsuo Miwa
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Patent number: 5491234Abstract: 2,4-diaminopyrimidine derivatives as potentiators of chemotherapeutic agents in the treatment of cancer.Type: GrantFiled: October 14, 1993Date of Patent: February 13, 1996Assignee: Pfizer Inc.Inventors: Jotham W. Coe, Anton F. J. Fliri, Takushi Kaneko, Eric R. Larson
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Patent number: 5461152Abstract: Compounds of the formulae I and Ia and their racemates ##STR1## in which A is --CH.sub.2 -- or --CH.sub.2 CH.sub.2 --, R.sub.1 is hydrogen or a protective group, R.sub.2 is hydrogen or a protective group or a radical forming a phosphorus-containing nucleotide bridge group and B is a purine or pyrimidine radical or an analogue thereof, can be used as antiviral active ingredients or for the preparation of biologically active oligonucleotides.Type: GrantFiled: June 28, 1993Date of Patent: October 24, 1995Assignee: Ciba-Geigy CorporationInventors: Karl-Heinz Altmann, Rene Imwinkelried, Albert Eschenmoser
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Patent number: 5440040Abstract: The present invention is directed to compounds of formula (I), ##STR1## wherein R.sup.1 is OH, NH.sub.2 ; R.sup.2 is a heteroaromatic or aromatic substituent; R.sup.3 is H, OH, F, OCH.sub.3 ; R.sup.4 is H, F, OH or an ether or ester residue thereof, OCH.sub.3, CN, C.dbd.CH, N.sub.3 ; R.sup.5 is OH or an ether or ester residue thereof including mono, di- and triphosphate esters (.alpha.), wherein n is 0 or 1 and M is hydrogen or a pharmaceutically acceptable counterion such as sodium, potassium, ammonium or alkylammonium; and pharmaceutically acceptable salts thereof; and pharmaceutical compositions comprising said compounds can be used for therapeutic treatment of virus infections. The present invention is also directed to compounds of formula (I'), ##STR2## wherein R.sup.1 and R.sup.2 are as defined above, as intermediates.Type: GrantFiled: January 18, 1991Date of Patent: August 8, 1995Assignee: Medivir ABInventor: Salo Gronowitz
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Patent number: 5426110Abstract: The present invention provides novel pyrimidinyl-glutamic acid derivatives and intermediates thereto. Further provided are methods for inhibiting dihydrofolate reductase in mammals and for treating susceptible neoplasms in mammals, particularly humans.Type: GrantFiled: October 6, 1993Date of Patent: June 20, 1995Assignee: Eli Lilly and CompanyInventors: Lynn S. Gossett, Chuan Shih
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Patent number: 5317021Abstract: Amino acid compounds of the formula: ##STR1## wherein the various symbols are as hereinafter described, which have inhibiting effect on enkephalinase.Type: GrantFiled: November 4, 1992Date of Patent: May 31, 1994Assignee: ONO Pharmaceutical Co., Ltd.Inventors: Masanori Kawamura, Yoshinobu Arai, Hideki Aishita
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Patent number: 5312919Abstract: This invention relates to novel photooxidation products, and derivatives thereof, of Merocyanine 540, their preparation and their uses as anticancer and antiviral agents.Type: GrantFiled: June 12, 1992Date of Patent: May 17, 1994Assignee: Baylor Research InstituteInventors: Kirpal S. Gulliya, Burchard Franck, J. Lester Matthews, Udo Schneider
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Patent number: 5292740Abstract: The novel sulfonamides of formula I, ##STR1## in which the symbols R.sup.1 -R.sup.9, R.sup.a, R.sup.b, X, Y and n have the significance given in the description and salts thereof can be used for the treatment of circulatory disorders, especially hypertension, ischemia, vasopasms and angina pectoris.Type: GrantFiled: June 9, 1992Date of Patent: March 8, 1994Assignee: Hoffmann-La Roche Inc.Inventors: Kaspar Burri, Martine Clozel, Walter Fischli, Georges Hirth, Bernd-Michael Loffler, Werner Neidhart, Henri Ramuz
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Patent number: 5205962Abstract: The invention relates to pyridine derivatives of the formula I ##STR1## wherein R.sup.1, A.sup.1, E.sup.1, n, A.sup.2, Z.sup.2, X and Y have the meaning given in claim 1.Type: GrantFiled: February 6, 1991Date of Patent: April 27, 1993Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: David Coates, Simon Greenfield, Ian C. Sage, Robert Clemitson, Herbert Plach, Volker Reiffenrath
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Patent number: 5169856Abstract: The present invention relates to unsaturated carboxylic acid amide derivatives of the formula ##STR1## wherein ring A stands for an optionally substituted aromatic ring; R.sup.1 stands for a hydrogen atom or an optionally substituted hydrocarbon residue or forms an optionally substituted carbocyclic ring with the adjacent group --CH.dbd.C-- together with two carbon atoms constituting the ring A; R.sup.2 stands for a hydrogen atom, an optionally substituted hydrocarbon residue or an optionally substituted acyl group; R.sup.3 stands for an optionally substituted hydrocarbon residue; and n denotes an integer ranging from 2 to 6, and salts thereof, as well as the production thereof.The compounds of the present invention act on the central nervous system of mammals and has a strong anti-cholinesterase activity, which can be used for the prophylaxis and therapy of, for example, senile dementia, Alzheimer's diseases, Huntington's chorea, et., and are useful as medicines.Type: GrantFiled: February 6, 1989Date of Patent: December 8, 1992Assignee: Takeda Chemical Industries, Inc.Inventors: Giichi Goto, Akinobu Nagaoka
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Patent number: 5166206Abstract: Substituted pyrimidines, pyrimidinones and pyridopyrimidines of formula (I) are as angiotensin II antagonists useful in the treatment of hypertension, ocular hypertension and certain CNS ailments: ##STR1## wherein K is --N(R.sup.8a)--C(.dbd.M) or --N.dbd.C(R.sup.8b) where M is O or NR.sup.22.Type: GrantFiled: March 27, 1991Date of Patent: November 24, 1992Assignee: Merck & Co., Inc.Inventors: Eric E. Allen, William J. Greenlee, Malcolm MacCoss, Arthur A. Patchett
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Patent number: 5132288Abstract: In vitro results indicate that trimethoprim may be ineffective against S. enteritides. However, in vivo results show that trimethoprim alone and in combination with polymyxin B sulfate is effective on S. enteritidis infections in poultry.Type: GrantFiled: April 27, 1990Date of Patent: July 21, 1992Assignee: Michael Foods, Inc.Inventors: Eric A. Johnson, Michael C. Goodnough
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Patent number: 5110986Abstract: This application relates to a process for preparing a N-t-alkyl-1,2-diacylhydrazine by reacting a 1,3,4-oxadiazole with a tertiary alkyl cation precursor in the presence of a strong acid catalyst. Preferably, the 1,3,4-oxadiazole is a 2,5-disubstituted-1,3,4-oxadiazole and more preferably a 2,5-diaryl-1,3,4-oxadiazole. The strong acid catalyst is preferably a sulfur containing acid and more preferably sulfuric acid.Type: GrantFiled: April 26, 1988Date of Patent: May 5, 1992Assignee: Rohm and Haas CompanyInventor: Martha J. Kelly
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Patent number: 5049671Abstract: The present invention relates to 6-substituted purine carbocyclic nucleosides and their use in medical therapy particularly in the treatment of HIV and HBV infections. Also provided are pharmaceutical formulations and processes for the preparation of compounds according to the invention.Type: GrantFiled: December 22, 1989Date of Patent: September 17, 1991Assignee: Burroughs Wellcome Co.Inventor: Susan M. Daluge
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Patent number: 5043443Abstract: Novel aminomethyloxooxazolidinyl arylbenzene derivatives, wherein the aryl includes the phenyl, substituted phenyl, pyridyl, and substituted pyridyl groups, such as (l)-N-{3-[4- (4'-pyridyl)phenyl]-2-oxooxazolidin-5-ylmethyl}acetamide, possess useful antibacterial activity.Type: GrantFiled: July 24, 1990Date of Patent: August 27, 1991Assignee: Du Pont Merck Pharmaceutical CompanyInventors: Randall K. Carlson, Chung-Ho Park, Walter A. Gregory
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Patent number: 4992444Abstract: 2,4-Diamino-5-phenylpyrimidines in the form of the free base or an acid addition salt thereof are provided having the structural formula (I): ##STR1## wherein R.sup.1 is an alkoxy, aralkoxy or a mono-substituted or disubstituted amino group, R.sup.2 is a nitro group, and R.sup.3 is an alkyl group. The compounds act as antifolate agents and are useful for therapeutic treatment, for example as antitumour agents, antipsoriatic agents, antibacterial agents, antitrypanosomal agents and antimalarial agents. Pharmaceutical preparations comprising these compounds for administration to mammals, and methods for preparing the compounds, are disclosed. Particularly useful new compounds, especially for antitumour therapy, have the structural formula IA: ##STR2## in which formula IA: n is 1-6; R.sub.1 represents hydrogen or alkyl; R.sup.4, R.sup.5 and R.sup.6, which may be identical or different, each represnt hydrogen, alkyl, alkoxy, halo, nitro, perfluoroalkyl, a group of formula --CO.sub.2 R.sup.a wherein R.sup.Type: GrantFiled: December 2, 1987Date of Patent: February 12, 1991Inventors: Malcolm F. G. Stevens, Roger J. Griffin, Michelle A. Meek
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Patent number: 4983608Abstract: This invention relates to N-heteroaryl-4-pyrimidinamines of the formula ##STR1## where R.sub.1 is hydrogen, loweralkyl, aryl, or arylloweralkyl; R.sub.2 and R.sub.3 are independently hydrogen or loweralkyl, or R.sub.2 and R.sub.3 taken together are aryl; R.sub.4 and R.sub.5 are independently hydrogen or lowealkyl, or R.sub.4 and R.sub.5 taken together are aryl; X is hydrogen, halogen, cyano, nitro, amino, loweralkyl, loweralkoxy, trifluoromethyl or ##STR2## where Y is hydrogen, halogen or loweralkyl; m is an integer of 1 to 3; and the pharmaceutically acceptable acid addition salts thereof and where applicable the geometrical and optical isomers and racemic mixtures thereof. The compounds of this invention display utility as memory enhancing agents and as analgesic agents.Type: GrantFiled: September 5, 1989Date of Patent: January 8, 1991Assignee: Hoechst-Roussell Pharmaceuticals, Inc.Inventors: Richard C. Effland, Joseph T. Klein, Larry Davis, Gordon E. Olsen
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Patent number: 4912112Abstract: Novel substituted 2,4-diamino-5-benzyl pyrimidines are described. The novel substances have antimicrobial activity and are particularly suitable for inhibiting the growth of mycobacteria. Combined with inhibitors such as diaminodiphenylsulphones, ring-substituted 4-aminodiphenylsulphones or ring and/or nitrogen-substituted diaminodiphenylsulphones, they have a marked synergistic activity.Type: GrantFiled: February 6, 1987Date of Patent: March 27, 1990Assignee: Saarstickstoff-Fatol GmbH Chem.-Pharm. FabrikInventors: Joachim Seydel, Rolf Haller, Manfred Kansy, Gerd Hachtel
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Patent number: 4908368Abstract: Novel heterocyclic compounds shown by the general formula ##STR1## or the pharmaceutically acceptable salts thereof useful as medicament in particular as antagonist of slow reacting substance of anaphylaxis(SRS-A).Type: GrantFiled: June 7, 1989Date of Patent: March 13, 1990Inventors: Kiyoshi Murase, Toshiyasu Mase, Hiromu Hara, Kenichi Tomioka
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Patent number: 4908470Abstract: Methyl 4-dimethylamino-3,5-dimethoxybenzoate, an intermediate in the preparation of the antibacterially active aditoprim, is obtained from 4-amino-3,5-dibromobenzoic acid by replacement of the bromine atoms by methoxy groups and subsequent methylation.Type: GrantFiled: November 30, 1988Date of Patent: March 13, 1990Assignee: Hoffman-La Roche Inc.Inventors: Alfredo Guerrato, Martin Karpf, Hanny K. Berger, Ivan Kompis, Markus Schlageter
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Patent number: 4902795Abstract: Antibacterially active new 1,8-bridged 4-quinolone-3-carboxylic acid derivatives of the formula ##STR1## in which Y is carboxyl or a derivative thereofR.sup.1, R.sup.2, R.sup.3, R.sup.4, X.sup.1, X.sup.2 and X.sup.5 are H or various radicals,Z is O, NH, substituted NH, ##STR2## or ##STR3## m and n are 0 or 1, and A, B, D and E are CH or substituted C or up to three of them are N,and physiologically acceptable salts thereof. Novel intermediates are described as well as processes for making the intermediates and end products.Type: GrantFiled: November 17, 1988Date of Patent: February 20, 1990Assignee: Bayer AktiengesellschaftInventors: Michael Schriewer, Klaus Crohe, Hans-Joachim Zeiler, Karl G. Metzger
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Patent number: 4871743Abstract: Pyrimidin-5-yl derivatives of L-glutamic acid are anti-neoplastic agents. A typical embodiment is N-(4-[4-(2,4-diamino-6-hydroxypyrimidin-5-yl)-butyl]-benzoyl)-L-glutamic acid.Type: GrantFiled: January 19, 1988Date of Patent: October 3, 1989Assignees: The Trustees of Princeton University, Eli Lilly and CompanyInventors: Edward C. Taylor, Philip M. Harrington, Chuan Shih
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Patent number: 4851030Abstract: Novel benzenesulfonamide compounds containing an ortho-heterocyclicmethylene substituent such as N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(5-methylthio-1,3,4-thiad iazol-2-ylmethyl)benzenesulfonamide are useful as preemergent and/or postemergent herbicides and/or plant growth regulants.Type: GrantFiled: December 8, 1986Date of Patent: July 25, 1989Assignee: E. I. Du Pont de Nemours and CompanyInventor: Morris P. Rorer
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Patent number: 4798893Abstract: A method for the synthesis of the 2-propanone (I) is described starting from alkoxide (II) through the lactone (IV). ##STR1## Excellent control of the location of the substitution on the phenyl ring is achieved and the reaction proceeds in high yield.Type: GrantFiled: September 21, 1987Date of Patent: January 17, 1989Assignee: McNeilab, Inc.Inventors: David A. Cherry, Cynthia A. Maryanoff, John E. Mills, Roy A. Olofson, James D. Rodgers
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Patent number: 4792557Abstract: 2,4-Diamino-5-benzylpyrimidines of the formula ##STR1## wherein R.sup.1, R.sup.2, A, Z and n are as hereinafter set forth, are described. The 2,4-diamino-5-benzylpyrimidines of the invention have useful antibacterial activity. More particularly, they inhibit bacterial dihydrofolate reductase and potentiate the antibacterial activity of sulfonamides.Type: GrantFiled: January 14, 1987Date of Patent: December 20, 1988Assignee: Hoffman-La Roche Inc.Inventors: Ivan Kompis, G/e/ rald Rey-Bellet, Guido Zanetti
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Patent number: 4789743Abstract: The invention relates to a process for the preparaton of compounds of the formula I by reacting an alkali metal alcoholate with a compound of the formula II in the presence of an aliphatic ester such as methyl formate, and then condensing guanidine with the resulting compound of the formula III.The compound of the formula II can be prepared by reacting the corresponding benzaldehyde with acrylonitrile in the presence of diazabicyclo-2,2,2,-octane.Type: GrantFiled: July 31, 1987Date of Patent: December 6, 1988Assignee: Societe Anonyme: Sanofi Pharma S.A. - Succursale de CarougeInventor: Abram Becker
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Patent number: 4761475Abstract: Novel 2,4-diaminopyrimidines having substituted heterobicyclomethyl moieties in the 5-position have superior antibacterial properties.Type: GrantFiled: March 12, 1986Date of Patent: August 2, 1988Inventors: Susan M. Daluge, Paul M. Skonezny
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Patent number: 4725600Abstract: The invention relates to pyrimidine compounds of the formula: ##STR1## wherein the substituents R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are as herein defined, having activity as a cardiotonic, anti-hypertensive, cerebrovascular vasodilator and anti-platelet aggregation agent.Type: GrantFiled: July 5, 1985Date of Patent: February 16, 1988Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Takao Takaya, Masayoshi Murata, Kiyotaka Ito
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Patent number: 4708732Abstract: Herbicidal compounds having the formula ##STR1## wherein R.sup.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, phenyl or substituted phenyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.1 and R.sup.2 together are C.sub.2 -C.sub.5 alkylene;R.sup.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, phenyl or substituted phenyl, with the proviso that R.sup.1 and R.sup.3 are not both phenyl or substituted phenyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.3 and R.sup.4 together are oxo;R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.6 is hydrogen or C.sub.1 -C.sub.4 alkyl; andR.sup.7 and R.sup.8 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.n -- wherein n 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.Type: GrantFiled: October 24, 1986Date of Patent: November 24, 1987Assignee: Stauffer Chemical CompanyInventor: Charles G. Carter
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Patent number: 4705792Abstract: 4-Amino-2-(imidazolidin-2-on-1-yl)-5-(3-trifluoromethylphenylaminocarbonyl) pyrimidine of the formula I ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 have the indicated meanings, and their physiologically tolerated acid addition salts for the prophylaxis and therapy of thromboses, and the use of these compounds for the preparation of a medicament for the prophylaxis and therapy of thromboses are described.Type: GrantFiled: June 25, 1986Date of Patent: November 10, 1987Assignee: Hoechst AktiengesellschaftInventors: Ernold Granzer, Klaus-Dieter Kampe
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Patent number: 4666627Abstract: Novel 4-heterocyclylvinyl-4'-styryl-biphenyls of the formula ##STR1## are described, i which A is an isoxazolyl, oxadiazolyl, pyrimidinyl or triazinyl radical which is unsubstituted or substituted by a non-chromophoric substituent, R.sub.1 is hydrogen or a non-chromophoric substituent and R.sub.2 is hydrogen, halogen, or alkyl; processes for the preparation of these compounds are also described.The novel 4-heterocyclylvinyl-4'-styryl-biphenyls can be used as fluorescent brighteners for high-molecular organic materials, in particular materials of polyamide and polyester, especially for polyester textiles.Type: GrantFiled: July 27, 1984Date of Patent: May 19, 1987Assignee: Ciba-Geigy CorporationInventor: Hans R. Meyer
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Patent number: 4603136Abstract: Novel 2,4-diamino-5-(substituted naphthylmethyl)pyrimidines have been found to have superior antibacterial activity.Type: GrantFiled: December 30, 1983Date of Patent: July 29, 1986Inventors: Susan M. Daluge, Paul M. Skonezny