Plural Sulfurs Or Nitrogens In The Five-membered Hetero Ring (e.g., Thiatriazole, Etc.) Patents (Class 544/134)
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Patent number: 4440933Abstract: Histamine H.sub.2 -receptor antagonists of the formula ##STR1## wherein A, m, Z, n and R.sup.1 are as defined herein, and their nontoxic pharmaceutically acceptable salts, hydrates and solvates are novel anti-ulcer agents which are prepared by ring closure of a substituted ethanediimidamide of the formula ##STR2## with a compound of the formulaR--S--Rin which R is as defined herein.Type: GrantFiled: March 16, 1983Date of Patent: April 3, 1984Assignee: Bristol-Myers CompanyInventor: Thomas A. Montzka
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Patent number: 4434174Abstract: 3-Phenoxy-2-hydroxypropylamines having an N-benzimidazolyalkyl substituent and similar compounds are described herein. They are obtained by the reaction of the appropriate imidazole-1-alkanamine with an epoxide, and they are useful primarily as .beta..sub.1 -agonists/.beta.-sympathomimetic agents.Type: GrantFiled: March 2, 1982Date of Patent: February 28, 1984Assignee: Berlex Laboratories, Inc.Inventors: Julius Diamond, Ronald A. Wohl
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Patent number: 4416817Abstract: Novel 3-methoxy-2-oxoazetidine derivatives, which are shown by the following formula ##STR1## wherein R.sub.1 is amino, acylated amino or protected amino, are of value as intermediates for the synthesis of useful compounds represented by the formula ##STR2## wherein R.sub.1 has the same meaning as defined above, as drugs in the treatment of bacterial infections.Type: GrantFiled: November 18, 1981Date of Patent: November 22, 1983Assignee: Takeda Chemical Industries, Ltd.Inventors: Taisuke Matsuo, Michihiko Ochiai
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Patent number: 4411899Abstract: There are disclosed substituted derivatives of amino alkane diols and related compounds as well as processes for the preparation of such compounds. These compounds are useful for the suppression of gastric acid secretions in mammals and compositions for such uses are also disclosed.Type: GrantFiled: December 21, 1981Date of Patent: October 25, 1983Assignee: Merck & Co., Inc.Inventors: John J. Baldwin, William C. Lumma, Jr.
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Patent number: 4399138Abstract: Novel alkanolamine derivatives of the formula: ##STR1## wherein Ar is phenyl or naphthyl which is unsubstituted or which bears one or two substituents selected from halogen, trifluoromethyl, hydroxy, amino, nitro, carbamoyl, carbamoylmethyl and cyano, and alkyl, alkenyl, alkoxy, alkenyloxy, alkylthio, alkanoyl and alkanoylamino each of up to 6 carbon atoms, or Ar is 4-indolyl, 4-benzo[b]thienyl, 5-benzo[1,4]dioxanyl, 4- or 5-indanyl, 5- or 6- 1,2,3,4-tetrahydronaphthyl), 2,3-dihydroxy-1,2,3,4-tetrahydronaphth-5-yl or 4- morpholino-1,2,5-thiadiazol-3-yl;wherein R is halogen;wherein A.sup.1 is alkylene of 2 to 6 carbon atoms; andwherein A.sup.2 is alkylene of 1 to 7 carbon atoms which in unsubstituted or bears a phenyl, hydroxy or carbamoyl substituent, or A.sup.2 is cycloalkylene of 3 to 6 carbon atoms;or acid-addition salts thereof.The compounds possess either .beta.-adrenergic blocking activity or diuretic activity or both such activities and may be used in the treatment of heart disease or hypertension.Type: GrantFiled: February 2, 1982Date of Patent: August 16, 1983Assignee: Imperial Chemical Industries PLCInventors: Jeffrey J. Barlow, Leslie H. Smith
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Patent number: 4394508Abstract: Histamine H.sub.2 -antagonists of the formula ##STR1## wherein p is 1 or 2; R.sup.1 is hydroxy, amino, substituted amino or a 5- to 9-membered fully saturated nitrogen-containing heterocyclic ring attached via its nitrogen atom; m is an integer of from 0 to 2; n is an integer of from 2 to 4; Z is sulfur, oxygen or methylene; and A is an optionally substituted phenyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, thiadiazolyl, oxadiazolyl, furyl, thienyl or pyridyl ring; and nontoxic pharmaceutically acceptable salts, hydrates, solvates or N-oxides thereof are novel anti-ulcer agents. Intermediates and processes for their preparation are disclosed.Type: GrantFiled: March 3, 1981Date of Patent: July 19, 1983Assignee: Bristol-Myers CompanyInventors: Ronnie R. Crenshaw, Aldo A. Algieri
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Patent number: 4380639Abstract: Histamine H.sub.2 -antagonists of the formula ##STR1## wherein p is 1 or 2; R.sup.1 is hydroxy, amino, substituted amino or a 5- to 9-membered fully saturated nitrogen-containing heterocyclic ring attached via its nitrogen atom; m is an integer of from 0 to 2; n is an integer of from 2 to 4; Z is sulfur, oxygen or methylene; and A is an optionally substituted phenyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, thiadiazolyl, oxadiazolyl, furyl, thienyl or pyridyl ring; and nontoxic pharmaceutically acceptable salts, hydrates, solvates or N-oxides thereof are novel anti-ulcer agents. Intermediates and processes for their preparation are disclosed.Type: GrantFiled: June 23, 1981Date of Patent: April 19, 1983Assignee: Bristol-Myers CompanyInventors: Ronnie R. Crenshaw, Aldo A. Algieri
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Patent number: 4380638Abstract: Histamine H.sub.2 -antagonists of the formula ##STR1## wherein p is 1 or 2; R.sup.1 is hydroxy, amino, substituted amino or a 5- to 9-membered fully saturated nitrogen-containing heterocyclic ring attached via its nitrogen atom; m is an integer of from 0 to 2; n is an integer of from 2 to 4; Z is sulfur, oxygen or methylene; and A is an optionally substituted phenyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, thiadiazolyl, oxadiazolyl, furyl, thienyl or pyridyl ring; and nontoxic pharmaceutically acceptable salts, hydrates, solvates or N-oxides thereof are novel anti-ulcer agents. Intermediates and processes for their preparation are disclosed.Type: GrantFiled: June 23, 1981Date of Patent: April 19, 1983Assignee: Bristol-Myers CompanyInventors: Ronnie R. Crenshaw, Aldo A. Algieri
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Patent number: 4378357Abstract: This invention relates to novel heterocyclic fungicides which are effective in controlling a broad spectrum of phytopathogenic fungi found in the four main classes of fungi namely Phycomycetes, Ascomycetes, Fungi Imperfecti, and Basidiomycetes. Certain of these compounds are especially effective in controlling sclerotial forming fungi such as Whetzelinia sclerotiorum=(Sclerotinia sclerotiorium) and Botrytis cinerea.Type: GrantFiled: December 16, 1977Date of Patent: March 29, 1983Assignee: Rohm and Haas CompanyInventors: George A. Miller, Lendon N. Pridgen
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Patent number: 4374248Abstract: Histamine H.sub.2 -antagonists of the formula ##STR1## wherein p is 1 or 2; R.sup.1 is hydroxy, amino, substituted amino or a 5- to 9-membered fully saturated nitrogen-containing heterocyclic ring attached via its nitrogen atom; m is an integer of from 0 to 2; n is an integer of from 2 to 4; Z is sulfur, oxygen or methylene; and A is an optionally substituted phenyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, thiadiazolyl, oxadiazolyl, furyl, thienyl or pyridyl ring; and nontoxic pharmaceutically acceptable salts, hydrates, solvates or N-oxides thereof are novel anit-ulcer agents. Intermediates and processes for their preparation are disclosed.Type: GrantFiled: June 23, 1981Date of Patent: February 15, 1983Assignee: Bristol-Myers CompanyInventors: Ronnie R. Crenshaw, Aldo A. Algieri
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Patent number: 4372953Abstract: Tetrazole derivatives of the formula: ##STR1## wherein R.sup.1 is a lower alkykl, phenyl or a group of the formula: --S(O).sub.l --A--(X).sub.m --R.sup.3, and R.sup.2 is hydrogen, a lower alkyl, phenyl or a cycloalkyl when R.sup.1 is the group --S(O).sub.l --A--(X).sub.m --R.sup.3, or R.sup.2 is a group of the formula: --B--CO--R.sup.4 when R.sup.1 is a lower alkyl or phenyl and a pharmaceutically acceptable salt thereof, which have prophylactic or therapeutic activities against peptic and/or duodenal ulcers and are useful as an anti-ulcer drug; processes for the preparation of the tetrazole derivatives; and pharmaceutical composition containing said tetrazole derivatives.Type: GrantFiled: February 27, 1981Date of Patent: February 8, 1983Assignee: Otsuka Pharmaceutical Company, LimitedInventors: Minoru Uchida, Takao Nishi, Kazuyuki Nakagawa
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Patent number: 4363808Abstract: 3-Phenoxy-2-hydroxypropylamines having an N-benzimidazolyalkyl substituent and similar compounds are described herein. They are obtained by the reaction of the appropriate imidazole-1-alkanamine with an epoxide, and they are useful primarily as .beta.-adrenergic blocking agents.Type: GrantFiled: May 7, 1981Date of Patent: December 14, 1982Assignee: Berlex Laboratories, Inc.Inventors: Julius Diamond, Ronald A. Wohl
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Patent number: 4362726Abstract: Substituted-1,2,5-thiadiazole-1-oxides, their preparation and pharmaceutical use as elastase inhibitors are disclosed.Type: GrantFiled: April 24, 1981Date of Patent: December 7, 1982Assignee: Merck & Co., Inc.Inventors: Joseph S. Amato, Sandor Karady, Leonard M. Weinstock
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Patent number: 4358596Abstract: A process for the preparation of 1,2,3-thiadiazol-5-yl ureas of the general formula ##STR1## in which a 1,2,3-thiadiazol-5-carbohydroxam acid derivative of the formula ##STR2## is dissolved in an inert organic solvent with an acid halide of the formulaR.sub.4 -X IIIto form an acylated derivative which then reacts with an amine of the formula ##STR3## to form the desired product.Type: GrantFiled: January 21, 1981Date of Patent: November 9, 1982Assignee: Schering AGInventor: Hans-Rudolf Kruger
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Patent number: 4346042Abstract: Processes for preparing (S) or (R) epihalohydrin and an (S) substituted glycerol intermediate are disclosed.Type: GrantFiled: May 5, 1980Date of Patent: August 24, 1982Assignee: Merck & Co., Inc.Inventors: John J. Baldwin, David E. McClure
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Patent number: 4341551Abstract: A process for producing compounds of 1,2,3-thiadiazole-5-carboxylic acid is described. These compounds are effective as herbicides, fungicides and plant growth controllers.Type: GrantFiled: March 5, 1980Date of Patent: July 27, 1982Assignee: Schering AGInventors: Hans-Rudolf Kruger, Friedrich Arndt, Dietrich Baumert, Reinhart Rusch
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Patent number: 4293462Abstract: The invention concerns a process for the manufacture of 7.beta.-amino-3-cephem-3-ol-4-carboxylic acid compounds by ring closure of esters of 2-[4-(substituted-thio)-3-acylamino-2-oxoazetidin-1-yl]-3-substituted-amin o-crotonic acids and solvolyzing the enamino group in the resulting 7.beta.-acylamino-3-substituted-amino-cephem-4-carboxylic acid esters.Type: GrantFiled: December 10, 1979Date of Patent: October 6, 1981Assignee: Ciba-Geigy CorporationInventors: Robert B. Woodward, Hans Bickel
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Patent number: 4281121Abstract: 1,3,4-thiadiazole-2-carboxylic acid derivatives of the formula ##STR1## wherein R is C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkinyl or C.sub.3 -C.sub.6 -cycloalkyl,R.sub.1 is C.sub.1 -C.sub.6 -alkoxycarbonyl, aminocarbonyl, C.sub.1 -C.sub.8 -alkylaminocarbonyl, C.sub.3 -C.sub.6 -cycloalkylaminocarbonyl, di-C.sub.1 -C.sub.8 alkylaminocarbonyl, cyclohexylmethylaminocarbonyl, alkoxyalkylaminocarbonyl, morpholinocarbonyl, pyrrolidinocarbonyl, piperidinocarbonyl or cyano,and n is 0.1 or 2.The compounds wherein n is 1 or 2 have both a high fungicidal and nematocidal activity. The compounds in which n is 0 are the starting products or intermediate products in making the compound in which a sulfonyl or sulfinyl group is present (n=1 or 2) but have also nematocidal properties of their own. All compounds of the invention avoid the undesirable environmental properties and other shortcomings of the prior art products, particularly those of the broadly used mercury compounds.Type: GrantFiled: December 6, 1979Date of Patent: July 28, 1981Assignee: Schering AktiengesellschaftInventors: Ludwig Nusslein, Dietrich Baumert, Ernst A. Pieroh
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Patent number: 4243404Abstract: 1,2,3-Thiadiazole-3-in-5-ylidene-urea derivative of the formula ##STR1## in which R.sub.1 is hydrogen or alkyl which may be substituted in one or several places by oxygen or sulfur and wherein R.sub.2 and R.sub.3 have the meaning as given in the attached specification and wherein X is oxygen or sulfur. The compounds have properties suited for controlling the natural growth and natural development of plants and in addition have a superior defoliating property without accompanying unpleasant odors.Type: GrantFiled: April 4, 1978Date of Patent: January 6, 1981Assignee: Schering AktiengesellschaftInventors: Hans-Rudolf Kruger, Friedrich Arndt, Reinhart Rusch
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Patent number: 4242350Abstract: The invention relates to a thiadiazole derivative of the formula I: ##STR1## in which Y is O, S, CH.sub.2, SO or a direct bond; m is 0 to 4 and n is 1 to 4 provided that when Y is S, O or SO m is 1 to 4, and when Y is O or SO n is 2 to 4; R.sup.1 is H or (C.sub.1-10)alkyl; A is 3,4-dioxocyclobuten-1,2-diyl or C=Z in which Z is O, S, NCN, NNO.sub.2, CHNO.sub.2, NCONH.sub.2, C(CN).sub.2, NCOR.sup.2, NCO.sub.2 R.sup.2, NSO.sub.2 R.sup.2 or NR.sup.3 in which R.sup.2 is (C.sub.1-6)alkyl or (C.sub.6-12)aryl and R.sup.3 is H or C.sub.1-6)alkyl; B is (C.sub.1-6)alkoxy, (C.sub.1-6)alkylthio or NR.sup.4 R.sup.5 in which R.sup.4 and R.sup.5 are independently H, (C.sub.1-10)alkyl, C.sub.3-6 (alkenyl), (C.sub.3-6)alkynyl, (C.sub.2-6)(primary hydroxy)alkyl, (C.sub.2-6)(primary amino)alkyl or C.sub.3-6)cycloalkyl or R.sup.4 and R.sup.5 are joined to form a 5- or 6- membered saturated ring optionally containing an additional O or NH: and the salts thereof.Type: GrantFiled: May 7, 1979Date of Patent: December 30, 1980Assignees: Imperial Chemical Industries Limited, ICI Americas Inc.Inventors: Tobias O. Yellin, Derrick M. Mant
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Patent number: 4226609Abstract: Disclosed are selected 3-trichloromethyl-5-cyclic amine-1,2,4-thiadiazole compounds. These compounds can be applied to or spread upon soil by themselves or in inert carriers or with nitrogen-containing fertilizers to inhibit ammonium nitrification in the soil.Type: GrantFiled: March 1, 1979Date of Patent: October 7, 1980Assignee: Olin CorporationInventors: Lawrence E. Katz, Walter A. Gay, Hansjuergen A. Schroeder
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Patent number: 4181517Abstract: 1,2,3-Thiadiazole-2-id-derivative of the formula ##STR1## in which R.sub.1 is hydrogen or alkyl which may be substituted in one or several places by oxygen or sulfur and wherein R.sub.1 has the meaning as given in the attached specification and wherein X is oxygen or sulfur and B is a univalent metal atom. The compounds have properties suited for controlling the natural growth and natural development of plants and in addition have a superior defoliating property.Type: GrantFiled: April 19, 1978Date of Patent: January 1, 1980Assignee: Schering AktiengesellschaftInventors: Hans-Rudolf Kruger, Reinhart Rusch, Friedrich Arndt
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Patent number: 4177054Abstract: 1,2,3-thiadiazole-5-carboxylic acid derivatives having herbicidal and growth regulating activity and having the formula ##STR1## in which R.sub.1 is hydrogen or is alkyl of which the chain may be interrupted in one or several places by oxygen or sulfur or which may be substituted by halogen and in whichX is(a) --Y--R.sub.2, wherein R.sub.2 is hydrogen, alkyl which may be substituted, aryl which may also be substituted, aryl-C.sub.1 -C.sub.2 -alkyl which may also be substituted, or a univalent metal equivalent and wherein Y is oxygen or sulfur, or(b) wherein X constitutes the residue ##STR2## wherein R.sub.3 and R.sub.4 may be the same or different and have the meaning further defined in claim 1 of the accompanying specification.The compounds are soil- or leaf-applicable herbicides with a high activity against seed weeds and resistant weeds.Type: GrantFiled: June 23, 1978Date of Patent: December 4, 1979Assignee: Schering AktiengesellschaftInventors: Friedrich Arndt, Hans-Rudolf Kruger, Reinhart Rusch
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Patent number: 4141987Abstract: Novel 1-heterocyclyloxy- or 1-aryloxy-3-amidoalkylamino-2-propanol derivatives, processes for their manufacture, pharmaceutical compositions containing them and methods of using them in the treatment of heart diseases. The compounds possess .beta.-adrenergic blocking activity. Representative of the compounds disclosed is 1-(4-indolyloxy)-3-.beta.-isobutyramidoethylamino-2-propanol.Type: GrantFiled: April 14, 1977Date of Patent: February 27, 1979Assignee: Imperial Chemical Industries LimitedInventor: Leslie H. Smith
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Patent number: 4126620Abstract: 2,4,5,6-Tetrahydrocyclopenta[c]pyrrole-4-carboxamide and 4-thiocarboxamide derivatives useful as antisecretory and anti-ulcer agents are prepared by hydrolysis or thiohydrolysis of the corresponding 2,4,5,6-tetrahydrocyclopenta[c]pyrrole-4-carbonitriles or, in the case of the thiocarboxamides, by reaction of the 4-carboxamide with phosphorus pentasulfide.Type: GrantFiled: February 25, 1977Date of Patent: November 21, 1978Assignee: Sterling Drug Inc.Inventors: Malcolm R. Bell, Rudolf Oesterlin
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Patent number: 4115409Abstract: Novel 1-aryloxy-3-carbamoylalkylamino-2-propanol derivatives, processes for their manufacture, pharmaceutical compositions containing them and methods of using them in the treatment of heart diseases. The compounds possess .beta.-adrenergic blocking activity. Representative of the compounds disclosed is 1-(2-cyanophenoxy)-3-.beta.-(N-2-furfurylcarbamoyl)ethylamino-2-propanol.Type: GrantFiled: November 26, 1976Date of Patent: September 19, 1978Assignee: Imperial Chemical Industries LimitedInventors: Michael Stewart Large, Leslie Harold Smith
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Patent number: 4097669Abstract: 2-Substituted-5-trifluoromethyl-1,3,4-thiadiazoles of the formula ##STR1## in which R is substituted alkyl, phenyl monosubstituted in the o- or m- position, polysubstituted phenyl, substituted phenylalkyl, phenylalkenyl, substituted phenylalkenyl, an optionally substituted 5-membered or 6-membered heterocyclic radical with 1 to 4 hetero-atoms selected from N and S atoms, optionally substituted benzimidazolyl or benzthiazolyl, optionally substituted naphthyl, quinolyl, cyano or one of the groups ##STR2## wherein R.sup.1 and R.sup.2 conjointly are a trimethylene, tetramethylene or pentamethylene group,X is oxygen or sulfur,R' and R" each independently is alkyl or, together with the nitrogen atom and optionally further hetero-atoms selected from O and N atoms, form an optionally substituted 6-membered or 7-membered ring, andN is 0, 1 or 2,Which possess fungicidal, bactericidal, arthropodicidal and insecticidal properties.Type: GrantFiled: July 14, 1976Date of Patent: June 27, 1978Assignee: Bayer AktiengesellschaftInventors: Josef Helmut Reisdorff, Wilhelm Brandes, Hans Scheinpflug, Bernhard Homeyer, Peter Roessler
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Patent number: 4086357Abstract: Novel 1-aryl-2-carbamoylalkylaminoethanol derivatives, processes for their manufacture, pharmaceutical compositions containing them and methods of using them in the treatment of heart diseases. The compounds possess .beta.-adrenergic blocking activity. Representative of the compounds disclosed is 1-(4-methanesulphonamidophenyl)-2-(.beta.-N-2-furfurylcarbamoylethylamino) ethanol.Type: GrantFiled: November 26, 1976Date of Patent: April 25, 1978Assignee: Imperial Chemical Industries LimitedInventors: Michael Stewart Large, Leslie Harold Smith
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Patent number: 4076939Abstract: Novel 2-(4-substituted-1,2,5-thiadiazol-3-yloxy)acetaldehydes are disclosed. These acetaldehydes are useful as intermediates for preparing certain .beta.-adrenergic blocking agents.Type: GrantFiled: February 8, 1977Date of Patent: February 28, 1978Assignee: Merck Sharp & Dohme (I.A.) CorporationInventor: Patrice C. Belanger
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Patent number: 4074049Abstract: A series of 1,3,4-thiadiazoles substituted in the 2,5-position with amino, dialkylaminoalkylthio, or heterocyclicalkylthio are useful as antithrombotic agents.Type: GrantFiled: November 19, 1976Date of Patent: February 14, 1978Assignee: The Dow Chemical CompanyInventors: Louis E. Begin, Joseph E. Dunbar
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Patent number: 4055568Abstract: Dyes of the formula: ##STR1## in which Z is unsubstituted or substituted alkyl, alkenyl, cycloalkyl, aralkyl, aryl or heteroaryl or a radical of the formula ##STR2## Z.sup.1, Z.sup.2, Z.sup.3 and Z.sup.4 are hydrogen or unsubstituted or substituted alkyl, cycloalkyl, aralkyl or aryl;Z.sup.1 and Z.sup.2 or Z.sup.3 and Z.sup.4 may together with the nitrogen form a heterocyclic ring;Z.sup.1 and Z.sup.2 together with the nitrogen may be a saturated unsubstituted or substituted 5-membered or 6-membered ring condensed on in the ortho-position to the nitrogen;B is unsubstituted or substituted alkyl, alkenyl, cycloalkyl, aralkyl, aryl or heteroaryl; andX is imino or oxygen.The dyes give brilliant yellow dyeings having good fastness properties on textile materials, particularly polyester materials, and in plastics.Type: GrantFiled: June 7, 1976Date of Patent: October 25, 1977Assignee: BASF AktiengesellschaftInventors: Manfred Patsch, Christos Vamvakaris
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Patent number: 4044131Abstract: 2-Morpholinol derivatives characterized by having an aryloxymethyl radical attached to the 6 position and an alkyl or alkynyl radical attached to the nitrogen at the 4 position are disclosed. The derivatives may be optionally substituted at the 2 position with an alkyl or aryl group and the hydroxyl function at position 2 may be replaced with an alkoxy group. The 2-morpholinol derivatives of this invention are useful .beta.-adrenergic blocking and antifungal agents. Methods for the preparation and use of these derivatives are also described.Type: GrantFiled: November 24, 1975Date of Patent: August 23, 1977Assignee: American Home Products CorporationInventors: Andre A. Asselin, Leslie G. Humber