Sulfur Containing Hetero Ring Patents (Class 548/527)
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Patent number: 5352831Abstract: Oligomeric cyanoguanidines of formula I ##STR1## wherein, for example, R.sup.1 and R.sup.2 are each phenyl, R is 1,4-phenylene and n is an integer from 1 to 20, are suitable latent hardeners for epoxy resins. They are readily soluble in solvents suitable for the application of epoxy resins, and the cured products obtained therewith have a high glass transition temperature.Type: GrantFiled: July 14, 1992Date of Patent: October 4, 1994Assignee: Ciba-Geigy CorporationInventors: Peter Flury, Martin Roth, Sameer H. Eldin
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Patent number: 5336682Abstract: Fungicidally active compounds of the formula ##STR1## and stereoisomers 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: December 10, 1991Date of Patent: August 9, 1994Assignee: Imperial Chemical Industries Public Limited CompanyInventors: Paul deFraine, Brian K. Snell, Kevin Beautement, Vivienne M. Anthony, John M. Clough
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Patent number: 5334602Abstract: New aryloxy-alkylamine derivatives of the general formula I ##STR1## in which A signifies a benzene or thiophene ring, R and R.sub.1, independently of one another, each hydrogen, alkyl, halogen, CF.sub.3 or alkoxy, R.sub.2 alkyl, cycloalkyl, alkenyl, alkynyl, alkaryl or saturated or unsaturated aliphatic or aromatic acyl, R.sub.3 and R.sub.4 in each case hydrogen, alkyl, alkenyl, alkynyl or cycloalkyl with, in each case, up to 8 C-atoms, whereby R.sub.3 and R.sub.4 can be the same or different but are not simultaneously hydrogen or R.sub.3 and R.sub.4, together with the nitrogen atom connecting them, form a 5- to 7-membered saturated ring or a saturated heterocyclic ring which can possibly contain an oxygen or nitrogen atom as a further heteroatom in the ring, whereby an additional nitrogen atom can be substituted by an alkyl radical with up to 3 C-atoms, and their acid-addition salts possess interesting pharmaceutical properties and are especially suitable as anti-arrhythmics.Type: GrantFiled: September 3, 1991Date of Patent: August 2, 1994Assignee: Laevosan-Gesellschaft GmbHInventors: Bernhard Lotz, Gerhard Greier
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Patent number: 5332757Abstract: The invention concerns oxime derivatives of the formula I ##STR1## wherein R.sup.4 includes hydrogen, carboxy, carbamoyl, amino, cyano, trifluoromethyl, (1-4C)alkylamino, di-(1-4C)alkylamino and (1-4C)alkyl;R.sup.5 includes hydrogen, (1-4C)alkyl, (3-4C)alkenyl, (3-4C)alkynyl, (2-5C)alkanoyl, halogeno-(2-4C)alkyl and hydroxy-(2-4C)alkyl;Ar.sup.1 is phenylene or a heteroaryl diradical;A.sup.1 is a direct link to X.sup.1, or A.sup.1 is (1-4C)alkylene;X.sup.1 is oxy, thio, sulphinyl or sulphonyl;Ar.sup.2 is phenylene or a heteroaryl diradical;R.sup.1 is (1-4C)alkyl, (3-4C)alkenyl or (3-4C)alkynyl; andR.sup.2 and R.sup.3 together form a group of the formula -A.sup.2 -X.sup.2 -A.sup.3 - which together with the carbon atom to which A.sup.2 and A.sup.3 are attached define a ring having 5 or 6 ring atoms, wherein each of A.sup.2 and A.sup.3 is (1-3C)alkylene and X.sup.Type: GrantFiled: February 8, 1993Date of Patent: July 26, 1994Assignees: Zeneca Limited, Zeneca PHARMA S AInventors: Thomas G. C. Bird, Patrick Ple
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Patent number: 5326759Abstract: Novel 9-amino-7-(substituted amino)-6-demethyl-6-deoxytetracyclines having activity against a wide spectrum of organisms including organisms which are resistant to tetracyclines are disclosed. Also disclosed are intermediates and methods for making the novel compounds of the present invention.Type: GrantFiled: November 1, 1993Date of Patent: July 5, 1994Assignee: American Cyanamid CompanyInventors: Joseph J. Hlavka, Phaik-Eng Sum, Yakov Gluzman, Ving J. Lee
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Patent number: 5300499Abstract: The present invention provides novel carbonic anhyrase inhibitors represented by the structural formula: ##STR1## wherein R.sub.1 and R.sub.2 are, for example, independently (a) hydrogen; or(b) OR.sub.4, wherein R.sub.4 is hydrogen or C.sub.1-7 alkyl; or(c) NR.sub.5 R.sub.6, wherein R.sub.5 and R.sub.6 are independently hydrogen, or C.sub.1-7 alkyl, or C.sub.1-7 alkyl substituted with one or more halogen or OR.sub.4 ; or(d) --COR.sub.7, wherein R.sub.7 is hydrogen, C.sub.1-7 alkyl, or NR.sub.5 R.sub.6 ; or(e) --SR.sub.8, wherein R.sub.8 is hydrogen or C.sub.1-7 alkyl, or C.sub.1-7 alkyl substituted with one or more halogen, or OR.sub.4 ; or(f) C.sub.1-7 alkyl, or C.sub.1-7 alkyl substituted with one or more halogen, or OR.sub.4 or NR.sub.5 R.sub.6 ; or(g) R.sub.1 and R.sub.2 are together(i) .dbd.O, or(ii) .dbd.NOR.sub.8 or(iii) .dbd.S;and R.sub.3 is(h) C.sub.1-7 alkyl or C.sub.1-7 substituted with one or more halogen, OR.sub.4 or NR.sub.5 R.sub.6.Type: GrantFiled: September 2, 1992Date of Patent: April 5, 1994Assignee: Allergan, Inc.Inventor: Ken Chow
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Patent number: 5262431Abstract: A novel prolinal derivative of general formula: ##STR1## [wherein A 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 alkoxy 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: February 19, 1992Date of Patent: November 16, 1993Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Masaaki Toda, Shuichi Ohuchida, Hiroyuki Ohno
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Patent number: 5260319Abstract: Novel thienobenzoxepins and naphthothiophenes, intermediates and processes for the preparation thereof, and methods of alleviating pain utilizing compounds or compositions thereof are disclosed.Type: GrantFiled: March 19, 1993Date of Patent: November 9, 1993Assignee: Hoechst-Roussel Pharmaceuticals IncorporatedInventors: Richard C. Effland, David G. Wettlaufer
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Patent number: 5256657Abstract: Compounds having the structural formula ##STR1## wherein X is HONH or HO and especially wherein the carbon atom bearing CH.sub.2 R.sup.1 has the R-configuration, the carbon atom bearing CH.sub.2 R.sup.2 has the S-configuration, R.sup.1 is isopropyl, R.sup.2 is 3-indolyl, m is 2, n is 0, p is 2 and R.sup.3 and R.sup.4 taken alone are each methyl or R.sup.3 and R.sup.4 taken together with N are morpholino and pharmaceutically acceptable acid addition salts or solvates or acid addition salts-solvates thereof, which are matrix-metalloprotease inhibitors useful in treatment of disease in which matrix-metalloprotease promoted connective tissue remodelling is a causative factor, for example, rheumatoid arthritis and cancer, and a method of preparation and method of use thereof and methods of preparation of intermediates therefor are disclosed.Type: GrantFiled: August 19, 1991Date of Patent: October 26, 1993Assignee: Sterling Winthrop, Inc.Inventors: Jasbir Singh, Barry A. Morgan, James A. Gainor, Thomas D. Gordon, Robert C. Wahl
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Patent number: 5254579Abstract: N-(5-thioxo-L-prolyl)-L-cysteine and derivatives thereof, having interesting mucolytic-expectorant, antioxidant (radical-scavenger), antielastase, antiemphysema, immunostimulating and hepatoprotective activities and a low toxicity are described, as well as processes for the preparation thereof and pharmaceutical formulations for the use in therapy.Type: GrantFiled: May 8, 1992Date of Patent: October 19, 1993Assignee: Poli Industria Chimica S.p.A.Inventors: Stefano Poli, Germano Coppi, Giovanni Signorelli
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Patent number: 5252589Abstract: There is disclosed a benzocycloheptene compound of the formula: ##STR1## wherein R.sup.1 is hydrogen atom, a halogen atom or a lower alkoxy group, R.sup.2 and R.sup.3 are independently selected from hydrogen atom, a lower alkyl group and a lower alkenyl group, or R.sup.2 and R.sup.3 combine together with adjacent nitrogen atom to form a heteromonocyclic group, or a pharmaceutically acceptable salt thereof, which has an excellent inhibitory activity against contraction of urinary bladder.Type: GrantFiled: December 14, 1992Date of Patent: October 12, 1993Assignee: Tanabe Seikayu Co., Ltd.Inventors: Masakatsu Ozeki, Kosuke Yasuda, Masamichi Morimoto, Tohru Ishizuka, Kunio Nosaka
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Patent number: 5250683Abstract: A taxane derivative of the formula ##STR1## wherein R.sub.1 and R.sub.3 are independently selected from the group comprising phenyl, naphthalene, C.sub.6 H.sub.5 CHCH--, and ##STR2## provided, however, R.sub.1 and R.sub.3 are not both phenyl;Q is CH.sub.3 --, (CH.sub.3).sub.3 C--, CH.sub.3 O--, Cl, Br, F, NO.sub.2, ##STR3## Z is --OT.sub.1, T.sub.1 is hydrogen, hydroxyl protecting group, or --COT.sub.2,T.sub.2 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkenyl, C.sub.1 -C.sub.6 alkynyl or monocylic aryl,Ac is acetyl, andE.sub.1 and E.sub.2 are independently selected from hydrogen and functional groups which increase the water solubility of the taxane derivative are useful as antitumor agents.Type: GrantFiled: April 3, 1992Date of Patent: October 5, 1993Assignee: Florida State UniversityInventors: Robert A. Holton, Hossain Nadizadeh, Seokchan Kim, Ronald J. Beidiger
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Patent number: 5243045Abstract: A taxane derivative of the formula ##STR1## wherein R.sub.1 is phenyl or substituted phenyl,R.sub.3 is CH.sub.3 O--, or CH.sub.3 CH.sub.2 O--,Z is --OT.sub.1,T.sub.1 is hydrogen, hydroxyl protecting group, or --COT.sub.2.T.sub.2 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkenyl, C.sub.1 -C.sub.6 alkynyl or monocylic aryl,Ac is acetyl, andE.sub.1 and E.sub.2 are independently selected from hydrogen and functional groups which increase the water solubility of the taxane derivative are useful as antitumor agents.Type: GrantFiled: April 3, 1992Date of Patent: September 7, 1993Assignee: Florida State UniversityInventors: Robert A. Holton, Ronald J. Beidiger
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Patent number: 5232978Abstract: Novel 1-(2-arylethyl)-pyrrolidines of the formula ##STR1## in which, Ar is a phenyl group which is unsubstituted or monosubstituted by OH, --O--CO--NH.sub.2, --O--CO--NHA, --O--CO--NA.sub.2, NH.sub.2, --NH--CHO, --NH--CO--A, --NH--CO--NH.sub.2, --NH--CO--NHA or NH--SO.sub.2 --A,R.sup.1 is A,R.sup.2 is a phenyl, naphthyl, thienyl, benzothienyl or pyridyl group which is unsubstituted or mono- or disubstituted by A, Hal, CF.sub.3, OH, OA, --O--CO--NH.sub.2, --O--CO--NHA, --O--CO--NA.sub.2, NO.sub.2, NH.sub.2, --NH--CHO, --NH--CO--A, --NH--CO--NH.sub.2, --NH--CO--NHA, --NH--SO.sub.2 A, --CO--A, --CONH.sub.2, --CONHA, --CONA.sub.2, --CH.sub.2 --CONH.sub.2 and/or --O--CH.sub.2 --CONH.sub.2,R.sup.3 is OH or CH.sub.2 OH,A is alkyl with 1-4 C atoms andHal is F, Cl, Br or I,or a pharmaceutically acceptable salt thereof for use as an analgesic in humans and veterinary medicine.Type: GrantFiled: November 1, 1991Date of Patent: August 3, 1993Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Rudolf Gottschlich, Karl-August Ackermann, Helmut Prucher, Andrew Barbar, Anton Haase, Hartmut Greiner, Gerd Bartoszyk
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Patent number: 5227400Abstract: A taxane derivative of the formula ##STR1## wherein ##STR2## Z is --OT.sub.1, T.sub.1 is hydrogen, hydroxyl protecting group, or --COT.sub.2,T.sub.2 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkenyl, C.sub.1 -C.sub.6 alkynyl or monocylic aryl,R.sub.3 is benzoyl, substituted benzoyl or C.sub.1 -C.sub.6 alkoxycarbonyl,Ac is acetyl, andE.sub.1 and E.sub.2 are independently selected from hydrogen and functional groups which increase the water solubility of the taxane derivative are useful as antitumor agents.Type: GrantFiled: April 3, 1992Date of Patent: July 13, 1993Assignee: Florida State UniversityInventors: Robert A. Holton, Hossain Nadizadeh, Ronald J. Beidiger
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Patent number: 5214056Abstract: A 1,3,2-dioxathiolane oxide derivative is represented by the following formula: ##STR1## wherein X represents --S(O)-- or --S(O).sub.2 --;R.sup.1 represents a hydrogen atom, an alkali metal atom, a benzyl group, or a lower alkyl group;R.sup.2 represents a lower alkyl group which may be substituted with a methylthio group, or a benzyl group, andR.sup.3 and R.sup.4 may be the same or different and independently represent a hydrogen atom, an alkyl group having one to ten carbon atoms, a lower alkyl group substituted with a guanidyl group, a cycloalkyl group having 3 to 6 carbon atoms, a phenyl group, a benzyl group, or a phenethyl group, or together form an alkylene group.Type: GrantFiled: August 20, 1991Date of Patent: May 25, 1993Assignee: Japan Tobacco Inc.Inventors: Jun-ichi Haruta, Masahiro Tanaka, Itsuo Uchida, Akira Ohta, Shin Hara
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Patent number: 5210217Abstract: Electrically conducting homo- and/or copolymers and/or tripolymers can be produced from novel monomers, such as a 3-substituted 2,5-di(2-thienyl)pyrrole. The polymers exhibit unexpectedly high stability and conductivities, and can be functionalized, such as with an enzyme, like glucose oxidase, or an ion-specific binding site, like a crown ether, or an antigen, without adversely affecting the conductivity of the polymer. The functionalized, conducting polymer can be used in a diagnostic device to determine the presence and concentration of a specific analyte in a liquid medium.Type: GrantFiled: April 10, 1989Date of Patent: May 11, 1993Assignee: Miles Inc.Inventors: James P. Albarella, J. Oakey Noell, Paul O. Vogelhut, Frederick E. Ward, deceased
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Patent number: 5192777Abstract: Compounds of formula (I) ##STR1## and salts thereof, wherein R.sup.1 represents a methyl, ethyl or ispropyl group; R.sup.2 represents a C.sub.2-7 alkyl group interrupted by an oxygen or sulphur atom or an aryl, aryl C.sub.1-7 alkyl or heteroaryl C.sub.1-7 alkyl group; OR.sup.3 is a hydroxyl group or a substituted hydroxyl group having up to 25 carbon atoms; and the group .dbd.NOR.sup.2 is in the E configuration.These compounds may be used for controlling insect, acarine, nematode or other pests.Type: GrantFiled: December 11, 1990Date of Patent: March 9, 1993Assignee: American Cyanamid CompanyInventors: Michael V. J. Ramsay, Edward P. Tiley, Derek R. Sutherland
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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: 5190961Abstract: Thiourea derivatives represented by the formula (I) ##STR1## wherein R.sub.1 and R.sub.2 are the same or different and each represents a lower alkyl group, or R.sub.1 or R.sub.2 taken together represent a group having the formula --(CH.sub.2).sub.m --in which m is 4 or 5, R.sub.3 represents a lower alkyl group or a cycloalkyl group or a group having the formula--(CH.sub.2).sub.l --R.sub.4 in which R.sub.4 is a phenyl, naphthyl, pyridyl, furyl or thienyl group optionally having 1-3 substituents selected from the group consisting of lower alkyl, lower alkoxy, phenoxy, lower alkylthio, hydroxy, halogen, nitro, cyano and trifluoromethyl, and l represents an integer of 0 to 2 and n represents an integer of 1 to 5 or a physiologically acceptable salt thereof.The compounds of the invention are useful as a therapeutic agent for peptic ulcers which is also effective on prevention of the recurrence after discontinuation of the administration due to the antimicrobial activity against Helicobacter pyroli.Type: GrantFiled: August 2, 1991Date of Patent: March 2, 1993Assignee: Terumo Kabushiki KaishaInventors: Hirokazu Hasegawa, Isamu Endo, Shingo Koyama, Masashi Isozaki, Yukari Yoshiyama, Shigenori Nozawa, Norio Arakawa
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Patent number: 5187290Abstract: Compounds of the formula ##STR1## wherein Z is oxygen or sulfur are disclosed. These compounds are useful as hypotensive agents due to their angiotensin converting enzyme inbitition activity and depending upon the definition of X may also be useful as analgesics due to their enkephalinase inhibition activity.Type: GrantFiled: September 29, 1986Date of Patent: February 16, 1993Assignee: E. R. Squibb & Sons, Inc.Inventor: Eric M. Gordon
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Patent number: 5182348Abstract: Compounds of the formula (1) ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 have the meanings given in the description, and the other radicals have the following meanings:X, Y and Z denote identical or different divalent radicals --O--, --S--, --N(R.sup.9)-- or --C(R.sup.10).dbd.C(R.sup.11)--, with the proviso that at least one of the radicals, X, Y and Z is not a radical of the formula --C(R.sup.10).dbd.C(R.sup.11)--, and whereinR.sup.9 is a hydrogen atom, a branched or unbranched C.sub.1 - to C.sub.8 -alkyl radical or an optionally substituted phenyl radical, andR.sup.10 and R.sup.11 are, in each case, identical or different radicals which have one of the meanings of R.sup.1,R.sup.7 and R.sup.8 denote identical or different radicals, that is to say hydrogen atoms or C.sub.1 - to C.sub.6 -alkyl or phenyl radicals, andn, m and o denote identical or different integers with a value of from 1 to 10.Type: GrantFiled: August 19, 1991Date of Patent: January 26, 1993Assignee: Wacker-Chemie GmbHInventors: Hermann Braeunling, Richard Becker, Georg Bloechl
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Patent number: 5180735Abstract: The present invention relates to a compound of the formula: ##STR1## wherein A is halogen, N(O)mR.sup.1 R.sup.2, N.sup..sym. R.sup.1 R.sup.2 R.sup.3 .multidot.X.sup..crclbar., S(O)nR.sup.1 or S.sup..sym. (O)mR.sup.1 R.sup.2 .multidot.X.sup..crclbar. where R.sup.1, R.sup.2 and R.sup.3 are each optionally substituted hydrocarbon or heterocyclic group, X.sup..crclbar. is a counter anion; m is an integer of 0 or 1; n is an integer of 0 to 2; R.sup.1 and R.sup.2 may form a nitrogen-containing or a sulfur-containing heterocyclic ring, which may further form a condensed ring, with the adjacent nitrogen atom or sulfur atom, and these nitrogen-containing or sulfur-containing heterocyclic rings may have substituents, Z is O or NR.sup.4 where R.sup.Type: GrantFiled: August 29, 1990Date of Patent: January 19, 1993Assignee: Takeda Chemical Industries, Ltd.Inventors: Shoji Kishimoto, Shogo Marui, Takeshi Fujita
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Patent number: 5179207Abstract: Provided are certain substituted 2-aminothiazoles and 2-aminothiophenes which are useful as red colorants and as intermediates in the synthesis of bathochromic azo dyes. These compounds are prepared by reacting 2-aminothiophenes or 2-aminothiazoles, which contain a primary amino group, with 2-chloro-3-negatively-substituted maleimides. These compounds can be diazotized and coupled with azo components, for example, anilines, 1,2,3,4-tetrahydroquinolines, 2,3-dihydroindoles, and 3,4-dihydro-2H-1,4-benzoxazines to form bathochromic blue-cyan azo dyes.Type: GrantFiled: August 19, 1991Date of Patent: January 12, 1993Assignee: Eastman Kodak CompanyInventors: James J. Krutak, Max A. Weaver
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Patent number: 5175294Abstract: New thiophene compounds of the formula: ##STR1## in which: X represents hydrogen, halogen, C.sub.1 -C.sub.5 alkyl or alkoxy or dialkylamino;n represents 1 or 2;a represents an integer of from 2 to 6;b represents 2 or 3;c represents 1 or 2, and is such that b+c=4;R.sub.1 and R.sub.2 represent hydrogen or (C.sub.1 -C.sub.5)alkyl, or together with the carbon atom to which they are bonded form a hydrocarbon ring containing from 3 to 6 carbon atoms; andR and R' represent hydrogen or (C.sub.1 -C.sub.5)alkyl, or together with the nitrogen atom to which they are bonded form a pentagonal or hexagonal heterocycle optionally containing an oxygen atom or a second nitrogen atom which may itself be substituted; and their physiologically tolerable salts.The products of the invention can be used therapeutically especially in the treatment of pathologies that are characterized by a loss of bone tissue.Type: GrantFiled: August 5, 1991Date of Patent: December 29, 1992Assignee: Adir et CompagnieInventors: Michel Wierzbicki, Frederic Sauveur, Jacqueline Bonnet, Martine Brisset, Charles Tordjman
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Patent number: 5166346Abstract: Process for the preparation of thiophene derivatives and also new dihydrothiophene 1-oxides.Thiophene derivatives having an--optionally substituted--amino group on the thiophene ring are prepared by dehydrogenating dihydrothiophenes, substituted in a manner identical to that of the desired thiophene derivatives, by means of H.sub.2 O.sub.2, the dihydrothiophenes being reacted with H.sub.2 O.sub.2 in a first reaction stage in a neutral medium to give the corresponding sulfoxides, which are then rearranged into the thiophene derivatives by means of acid in the second reaction stage.The dihydrothiophene 1-oxides formed as intermediates in this reaction are new compounds. Like the thiophene derivatives formed from them by rearrangement with acid, they are intermediates, mainly in the sector of plant protection agents and pharmaceuticals.Type: GrantFiled: December 20, 1990Date of Patent: November 24, 1992Assignee: Hoechst AktiengesellschaftInventors: Robert Rippel, Hans-Wolfram Flemming, Manfred Rukwied
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Patent number: 5158950Abstract: 2-(1,3-Dithiol-2-ylidene)-2-[N-(substituted) carbamoly] acetate esters and salts thereof, having potent therapeutic or prophylactic effect for hepatic disorder, are provided. Processes for their preparation and intermediates in their preparation also are disclosed.Type: GrantFiled: May 23, 1990Date of Patent: October 27, 1992Assignee: Yuhan Corporation, Ltd.Inventors: Choong S. Kim, Jeong S. Chae, Young R. Choi, Jong W. Lee, Joung K. Yoo
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Patent number: 5143922Abstract: Novel tricyclic compounds having a TXA.sub.2 antagonizing activity represented by formula (I): ##STR1## possess a potent antagonizing action against thromboxane A.sub.2 and also an antiallergic and/or antihistaminic acitvity, and are expected to have preventive and therapeutic effects on ischemic diseases, cerebro-vascular diseases, etc.Type: GrantFiled: November 20, 1990Date of Patent: September 1, 1992Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Etsuo Oshima, Hiroyuki Obase, Akira Karasawa, Kazuhiro Kubo, Ichiro Miki, Akio Ishii, Hidee Ishii, Kenji Ohmori
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Patent number: 5140040Abstract: The present invention includes compounds represented by the formula: ##STR1## wherein n is 0 or 1; R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are independently selected from hydrogen, hydroxyl, amino, alkylamino, alkylsulfonylamino, loweralkyl, loweralkoxy, halo, and thioalkoxy; R.sub.1 and R.sub.2 or R.sub.2 and R.sub.3 taken together can form a methylenedioxy or ethylenedioxy bridge; R.sub.10 is independently selected from hydrogen, loweralkyl, phenyl, and substituted phenyl; R.sub.5 is loweralkyl; R.sub.9 is hydrogen or loweralkyl; R.sub.6 and R.sub.8 are hydrogen; and R.sub.7 is ##STR2## wherein m is 0, 1 or 2; X is CH.sub.2, O, S or N--CH.sub.3 ; or R.sub.7 is ##STR3## wherein s is 0, 1, or 2; Z is C or N; R.sub.11 and R.sub.12 are independently selected from hydrogen, halo, hydroxy, methoxy, thiomethoxy, amino and loweralkyl, or R.sub.11 and R.sub.12 taken together can form a methylenedioxy or ethylenedioxy bridge; or R.sub.7 is ##STR4## wherein t is 0 or 1; or R.sub.5 and R.sub.Type: GrantFiled: November 5, 1991Date of Patent: August 18, 1992Assignee: Abbott LaboratoriesInventors: John F. DeBernardis, Robert E. Zelle, Fatima Z. Basha
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Patent number: 5130328Abstract: This invention relates to N-alkanoylaminomethyl and N-aroylaminomethyl pyrrole compounds. It also relates to the use of said compounds as insecticidal and acaricidal agents and to a method of protecting plants from attack by insects and acarina by application of an N-alkanoylaminomethyl or N-aroylaminomethyl pyrrole to said plants or to the locus in which they are growing.Type: GrantFiled: September 6, 1991Date of Patent: July 14, 1992Assignee: American Cyanamid CompanyInventor: Venkataraman Kameswaran
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Patent number: 5128366Abstract: The compounds of the present invention inhibit HMG-CoA reductase, and subsequently suppress the synthesis of cholesterol. And they are useful in the treatment of hypercholesterolemia, hyperlipoproteinemia, and atherosclerosis. The compounds have the formula ##STR1## wherein R.sup.1, R.sup.2, and R.sup.3 each is independently hydrogen, optionally substituted lower alkyl, or optionally substituted aryl; R.sup.4 is lower alkyl, aralkyl, aryl, or heteroaryl, each of which is optionally substituted; X is vinylene or ethylene; Y is ##STR2## where R.sup.5 is hydrogen, lower alkyl, aryl, aralkyl, or a cation capable of forming a non-toxic pharmaceutically acceptable salt.Type: GrantFiled: May 30, 1991Date of Patent: July 7, 1992Assignee: Shinogi & Co., Ltd.Inventors: Kentaro Hirai, Teruyuki Ishiba, Haruo Koike, Masamichi Watanabe
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Patent number: 5128362Abstract: The present invention provides compounds of the formula ##STR1## or a pharmaceutically acceptable salt thereof wherein R.sub.1 is selected from hydrogen, halo, lower alkyl, lower alkoxy, or thioalkoxy; and R.sub.2 is lower alkoxy; or R.sub.1 and R.sub.2 together form a methylenedioxy or ethylenedioxy ring; R.sub.3 and R.sub.4 are independently selected from hydrogen, hydroxy, lower alkyl, lower alkoxy, lower alkylthio, (lower alkyl)amino, (lower alkylsulfonyl)amino, and halo; and R.sub.7 is selected from the group consisting of 2- or 3-thienyl, 2- or 3-furyl, and ##STR2## where R.sub.13 and R.sub.14 are independently selected from the group consisting of hydrogen, hydroxy, halogen, amino, lower alkyl, lower alkoxy, lower alkylthio, methylenedioxy, or ethylenedioxy.The compounds of the present invention selectively inhibit .alpha..sub.2 -adrenergic receptors as well as inhibit the uptake of biogenic amines and are thus useful in the treatment of certain cardiovascular and psychiatric disorders.Type: GrantFiled: January 25, 1990Date of Patent: July 7, 1992Assignee: Abbott LaboratoriesInventors: John F. DeBernardis, Robert E. Zelle, Fatima Z. Basha
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Patent number: 5120746Abstract: This invention relates to amine derivatives and salts thereof. These compounds have an anti-ulcer activity which is effective to human beings and animals. This disclosure relates to such compound, a process for the preparation thereof and an anti-ulcer agent containing the same.Type: GrantFiled: March 30, 1990Date of Patent: June 9, 1992Assignee: Toyama Chemical Co., Ltd.Inventors: Shiro Hirai, Hiroshi Hirano, Hirotoshi Arai, Yasuo Kiba, Hisanari Shibata, Yoshikazu Kusayanag, Minako Yotsuji, Kazuhiko Hashiba, Kikuko Tanada
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Patent number: 5112847Abstract: Prolinal derivatives of the formula ##STR1## wherein A is a group of the general formula ##STR2## wherein one of R.sup.1 and R.sup.2 is a hydrogen atom and the other is an 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 represent the same or different alkyl group of from 1 to 4 carbon atom(s) or a group of the formula ##STR3## wherein m represents an integer of from 3 to 6, n represents an integer of from 3 to 10, D represents a specified heterocyclic ring which is unsubstituted or substituted. These derivatives possess inhibitory activity on prolyl endopeptidase and therefor are useful as treating and/or preventing agents for amnesia.Type: GrantFiled: June 12, 1990Date of Patent: May 12, 1992Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Masaaki Toda, Shuichi Ohuchida, Hiroyuki Ohno
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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: 5109017Abstract: Compounds of the formula I, ##STR1## in which: R.sub.1 represents hydrogen or C.sub.1-6 alkyl,R.sub.2 represents hydrogen, C.sub.1-6 alkyl, C.sub.3-6 alkenyl, C.sub.3-6 alkynyl or C.sub.3-6 cycloalkyl,R.sub.3 represents one or more radicals selected from hydrogen, hydroxy, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, halogen, trifluoromethyl, amino, lower alkylamino or dilower alkylamino,R.sub.4 represents one or more radicals selected from hydrogen or C.sub.1-6 alkyl,A represents an alpha-amino acid acyl group or an alkoxycarbonyl group,and pharmaceutically acceptable salts thereof are useful as pharmaceuticals, in particular they possess N-methyl-(d)-aspartate (NMDA) blocking properties and are useful in the treatment and/or prevention of neurological disorders such as stroke, cerebral ischaemia, cerebral palsy, hypoglycaemia, epilepsy, Alzheimer's disease, Huntington's chorea, Olivo-ponto-cerebellar atrophy, perinatal asphyxia and anoxia.Type: GrantFiled: September 26, 1990Date of Patent: April 28, 1992Assignee: Fisons CorporationInventors: Richard J. Schmiesing, Ronald C. Griffith, Robert J. Murray
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Patent number: 5104869Abstract: Renin inhibiting compounds containing a single .alpha.-amino acid of the formula: ##STR1## and analogs thereof which inhibit the substrate-cleaving acting or renin, pharmaceutical compositions containing these compounds, processes for producing the compounds and methods of treating hypertension which employ the novel renin inhibitors.Type: GrantFiled: October 25, 1990Date of Patent: April 14, 1992Assignee: American Cyanamid CompanyInventors: Jay D. Albright, Charles Frederick, Jeremy I. Levin, Fuk-Wah Sum, Marvin F. Reich
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Patent number: 5091526Abstract: Biologically active, enantiomerically substantially pure intermediates of trans-hexahydro-benzo[d]naphtho[2,1-b]azepines are prepared.The present invention involves a process for preparing compounds of the general formula 3: ##STR1## wherein: R* is ##STR2## Each R.sup.1 is independently H or alkyl; Q is methylene, --O-- or --S--;m and n are independently variable and may each have a value of 0, 1 or 2, with the provisos that the sum of m and n is not greater than 3, that m may not equal zero when Q is --O-- or --S--, and that when Q is --CH.sub.2 --, m and n cannot both be zero;X is hydrogen, halo, alkyl, alkylthio, alkylsulfinyl, alkylsufonyl, hydroxy, alkoxy or trifluoromethyl;Y is hydrogen, hydroxy, alkoxy, --OC(O)NR.sup.2 R.sup.3, --OC(O)--R.sup.9, --N(R.sup.1).sub.2, --NHC(O)R.sup.1 or --OP(O)(OH)OR.sup.1,R.sup.2 and R.sup.3 are the same or different and each is hydrogen (provided that both are not hydrogen), alkyl, aralkyl, cycloalkyl, aryl, hydroxyalkyl, or alkoxyalkyl;in addition, when one of R.sup.Type: GrantFiled: January 8, 1991Date of Patent: February 25, 1992Assignee: Schering CorporationInventors: Joel G. Berger, John W. Clader
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Patent number: 5091406Abstract: A 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 orsubstituted by from one to three of halogen atom, alkyl or alkoxy group of from 1 to 4 carbon atom(s), nitro group or trifluoromethyl group.]. possess inhibitory activity on prolyl endopeptidase, and therefore be useful for treating and/or preventing agent for amnesia.Type: GrantFiled: February 7, 1990Date of Patent: February 25, 1992Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Masaaki Toda, Shuichi Ohuchida, Hiroyuki Ohno
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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: 5089519Abstract: The present invention includes compounds represented by the formula: ##STR1## wherein X is O or S;R.sub.1 and R.sub.2 are independently selected from the group consisting of hydrogen, hydroxy, halo, loweralkoxy, thioalkoxy and loweralkyl; or R.sub.1 and R.sub.2 taken together can form a methylenedioxy or ethylenedioxy bridge;R.sub.3 is loweralkyl;R.sub.4 is selected from ##STR2## wherein Y is O or S, R.sub.6 is hydrogen, methoxy or halo and m is 0 or 1;R.sub.5 is hydrogen, loweralkyl, phenyl or substituted phenyl wherein the phenyl ring is substituted with one, two or three substituents independently selected from loweralkyl, halo, hydroxy, loweralkoxy, amino and thioalkoxy; andR.sub.8 is hydrogen or R.sub.3 and R.sub.8 taken together form a pyrrolidine ring; or a pharmaceutically acceptable salt thereof.Type: GrantFiled: July 8, 1990Date of Patent: February 18, 1992Assignee: Abbott LaboratoriesInventors: John F. DeBernardis, David L. Arendsen, Robert E. Zelle
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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: 5071859Abstract: Novel N-substituted azaheterocyclic carboxylic acids and esters thereof in which an ether group forms part of the N-substituent, the compounds thus having the general formula I ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and each represents phenyl, 2-thienyl or 3-thienyl, 2-pyrrolyl or 3-pyrrolyl, substituted with one or more substituents selected among the following atoms or groups: hydrogen, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy or cyano; R.sup.3 and R.sup.4 each represents hydrogen or together represent a bond; m is 1 or 2 and n is 1 when m is 1 and n is 0 when m is 2; R.sup.5 and R.sup.6 each represents hydrogen or may--when m is 2--together represent a bond, and R.sup.7 is OH or C.sub.1 -C.sub.8 -alkoxy, p is 0 or 1 or 2, q is 0 or 1 or 2, R.sup.8 is H and C.sub.1 -C.sub.4 -alkyl, are potent inhibitors of GABA uptake from the synaptic cleft.Type: GrantFiled: December 14, 1989Date of Patent: December 10, 1991Inventors: Lars Jacob S. Knudsen, Anker S. Jorgensen, Knud E. Andersen, Ursula Sonnewald
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Patent number: 5068246Abstract: 3-Alkyl-4-arylpyrrolidine derivatives of the formula ##STR1## where R.sup.1 is alkenyl, alkynyl, cycloalkyl, cycloalkenyl, alkyl-cycloalkyl, cycloalkyl-alkyl, alkyl-cycloalkyl-alkyl, cycloalkenyl-alkyl, alkyl-cycloalkenyl, bicycloalkyl, bicycloalkylalkyl, alkyl-bicycloalkyl, heterocycloalkyl, heterocycloalkylmethyl, aryl, arylalkyl, alkylary, alkyl-aryl-alkyl,R.sup.2 is alkyl, alkoxy,R.sup.3 is alkylR.sup.4 is alkyl, alkenyl, alkynyl and phenylalkyl,X.sup.- is a plant-tolerated anion, andn is 0 or 1,their plant-tolerated salts, and fungicides containing these compounds.Type: GrantFiled: September 30, 1988Date of Patent: November 26, 1991Assignee: BASF AktiengesellschaftInventors: Matthias Zipplies, Hubert Sauter, Walter Himmele, Eberhard Ammermann, Ernst-Heinrich Pommer
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Patent number: 5068245Abstract: N-Substituted 3-arylpyrrolidine derivatives of the formula ##STR1## where R.sup.1 is 2,2-dimethylpropyl, 3,3-dimethylbutyl, 4,4-dimethylpentyl, 2,4,4-trimethylpentyl, 6-methylhept-2-yl, 3,5,5-trimethylhexyl, 6,10-dimethylundec-2-yl, 3-methylcyclohexyl, 3,3-dimethylcyclohexyl, 3,3,5-trimethylcyclohexyl, 3,3,5,5-tetramethylcyclohexyl, 4-methylcyclohexyl, 4-ethylcyclohexyl, 4-propylcyclohexyl, 4-isopropylcyclohexyl, 4-tert.-butylcyclohexyl, trans-4-tert.-butylcyclohexyl, 4(2-methylbut-2-yl)cyclohexyl, 4(2,4,4-trimethylpent-2-yl)-cyclohexyl, cyclododecanyl, C.sub.3 -C.sub.9 -trialkylsilyl-substituted C.sub.4 -C.sub.12 -cycloalkyl, 4-hydroxycyclohexyl, 4-hydroxy-3-methylcyclohexyl, 4-hydroxy-3,5-dimethylcyclohexyl, 4-hydroxy-3,3-dimethylcyclohexyl, 4-hydroxy-3,3,5-trimethylcyclohexyl, unsubstituted or hydroxy-, C.sub.1 -C.sub.9 -alkyl-, C.sub.1 -C.sub.5 -alkoxy- or C.sub.3 -C.sub.9 -trialkylsilyl-substituted C.sub.5 -C.sub.12 -cycloalkenyl,R.sup.1 is further bicycloalkyl,R.sup.1 is further 4-tert.Type: GrantFiled: September 30, 1988Date of Patent: November 26, 1991Assignee: BASF AktiengesellschaftInventors: Matthias Zipplies, Hubert Sauter, Franz Roehl, Walter Himmele, Eberhard Ammermann, Ernst-Heinrich Pommer
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Patent number: 5068355Abstract: The present invention relates to a number of innovative electrophilic substitution reactions involving 2,5-dithienylpyrrole (2,5-DTP). More specifically, these reactions are used in the synthesis of monomers for preparing functionalized conducting organic polymers.The electrophilic substitution reactions in this invention are accomplished under conditions not requiring the use of N-1 pyrrole blocking groups to direct reaction at the pyrrole C-3 position. This is because the steric bulk of the 2,5-dithienyl groups prevent N-acylation and therefore direct reactions with electrophiles at the pyrrole C-3 position.The reaction conditions chosen have also demonstrated a greater regioselectivity towards functionalization at the pyrrole 3-position than the basic reaction conditions suggested in the prior art. This result may be explained by an activation of the pyrrole 3-position towards electrophilic substitution. This is attributed to an electron donating resonance contribution of the 2,5 thienyl groups.Type: GrantFiled: October 4, 1990Date of Patent: November 26, 1991Assignee: Miles Inc.Inventors: James P. Albarella, Nan-Horng Lin
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Patent number: 5064962Abstract: Diaminothiophenes of the formula ##STR1## or tautomers thereof, where R.sup.1 and R.sup.2 are each hydrogen or together are ##STR2## where T.sup.1 is hydrogen, alkyl or phenyl, T.sup.2 and T.sup.3 are, independently of one another, alkyl or phenyl, or T.sup.2 and T.sup.3 together with the nitrogen linking them are a heterocyclic radical,R.sup.3 is substituted amino andR.sup.4 is alkanoyl, benzoyl, cyano, nitro or ##STR3## where T.sup.4 is hydrogen, alkyl or phenyl and T.sup.5 is the radical of a primary amine or of an active methylene compound,are prepared as described. The present diaminothiophene compound is useful in the synthesis of dyes, crop protection agents and pharmaceuticals.Type: GrantFiled: February 1, 1990Date of Patent: November 12, 1991Assignee: BASF AktiengesellschaftInventors: Matthias Wiesenfeldt, Karl-Heinz Etzbach
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Patent number: 5061704Abstract: 1. New thiophene compounds of the formula: ##STR1## in which: X represents hydrogen, halogen, C.sub.1 -C.sub.5 alkyl or alkoxy or dialkylamino;n represents 1 or 2;a represents an integer of from 2 to 6;b represents 2 or 3;c represents 1 or 2, and is such that b+c=4;R.sub.1 and R.sub.2 represent hydrogen or (C.sub.1 -C.sub.5)alkyl, or together with the carbon atom to which they are bonded form a hydrocarbon ring containing from 3 to 6 carbon atoms; andR and R' represent hydrogen or (C.sub.1 -C.sub.5)alkyl, or together with the nitrogen atom to which they are bonded form a pentagonal or hexagonal heterocycle optionally containing an oxygen atom or a second nitrogen atom which may itself be substituted; and their physiologically tolerable salts.The products of the invention can be used therapeutically especially in the treatment of pathologies that are characterized by a loss of bone tissue.2.Type: GrantFiled: November 23, 1990Date of Patent: October 29, 1991Assignee: Adir et CompagnieInventors: Michel Wierzbicki, Frederic Sauveur, Jacqueline Bonnet, Martine Brisset, Charles Tordjman
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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