Nitrogen Attached Directly To The Thiadiazole Ring By Nonionic Bonding Patents (Class 548/138)
  • Patent number: 5103007
    Abstract: Lipid derivatives represented by the formula: ##STR1## wherein R.sup.1 stands for an optionally substituted higher alkyl group, R.sup.2 stands for an optionally substituted lower alkyl group or an optionally substituted nitrogen-containing heterocyclic group, R.sup.3 stands for a tertiary amino group or a quaternary ammonium group, J stands for oxygen atom or S(O)t (where t deontes 0, 1 or 2), m and n respectively denotes 1 or 2, p denotes 0, 1 or 2, q and r respectively denote an integer of 2 to 5.and salts thereof have antitumor activities including differentiation-inducing activity and are useful as antitumor agents.
    Type: Grant
    Filed: October 27, 1989
    Date of Patent: April 7, 1992
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hiroaki Nomura, Hiroshi Akimoto, Keizo Inoue
  • Patent number: 5086053
    Abstract: The present invention relates to thiadiazole derivatives having the formula: ##STR1## in which: R.sub.1 represents a phenyl group, non-substituted or substitued 1 to 3 times by a halogen atom, preferably chlorine or fluorine, or by a C.sub.1 -C.sub.4 alkyl group, preferably the methyl group, or by a C.sub.1 -C.sub.4 alkoxy group, preferably the methoxy group, or by a hydroxy group or by a trifluoromethyl group or a phenyl group substituted simultaneously by 1 to 3 halogen atoms and by 1 or 2 methyl groupings;R.sub.2 represents hydrogen or a C.sub.1 -C.sub.4 alkyl group,R.sub.3 represents an alkylamino group or a heterocyclic group,Application: Drugs for treatment of notably senile dementia.
    Type: Grant
    Filed: August 16, 1989
    Date of Patent: February 4, 1992
    Assignee: Sanofi
    Inventors: Roger Brodin, Dominique Olliero, Paul Worms
  • Patent number: 5081245
    Abstract: A compound represented by the formula: ##STR1## wherein R represents a hydrogen atom or a lower alkyl group;R.sup.1 represents a higher alkyl group which may be substituted;R.sup.2 represents a hydrogen atom or a lower alkyl group, a lower alkanoyl group or a nitrogen-containing 5- to 7-membered heterocyclic group each of which may be substituted; X represents a divalent group represented by the formula:--(OCH.sub.2 CH.sub.2).sub.p --wherein p represents an integer of 1 to 5, a divalent group represented by the formula:--O(CH.sub.2).sub.q --wherein q represents an integer of 3 to 8, or a divalent group represented by the formula:--(OCH.sub.2 CH.sub.2).sub.p --J--(CH.sub.2).sub.q --wherein J represents an oxygen atom or a group represented by the formula: --S(O).sub.
    Type: Grant
    Filed: August 18, 1989
    Date of Patent: January 14, 1992
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hiroaki Nomura, Hiroshi Akimoto, Eiko Imamiya, Keizo Inoue
  • Patent number: 5071841
    Abstract: The present invention provides a sulfur-containing heterocyclic compound of the formula (I) ##STR1## wherein ring A is a benzene ring which may be substituted; R is a hydrogen atom or a hydrocarbon group which may be substituted; B is a carboxyl group which may be esterified or amidated; X is --CH(OH)-- or --CO--; k is 0 or 1; and k' is 0, 1 or 2 or a pharmaceutically acceptable salt thereof.Also, it provides a process for producing the compound (I) or a salt thereof and a pharmaceutical preparation for use in the treatment of osteoporosis comprising the compound (I) or salt thereof.The compounds (I) and salts thereof show excellent bone resorption inhibitory activity.
    Type: Grant
    Filed: December 28, 1989
    Date of Patent: December 10, 1991
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Takashi Sohda, Masao Tsuda, Iwao Yamazaki
  • Patent number: 5059598
    Abstract: Disclosed are compounds of the formula ##STR1## wherein: R.sup.1 is a lower alkyl group;R.sup.2 and R.sup.3 are each hydrogen or lower alkyl or R.sup.2 and R.sup.3 taken together may form --(CH.sub.2).sub.4 -- or --CH.dbd.CH--CH.dbd.CH--;.alpha. is a 5- or 6-membered heretoaromatic ring group containing 1 to 3 hetero-atoms selected from the group consisting of nitrogen, oxygen and sulfur, or a pyrazine-N-oxide ring, pyridazine-N-oxide ring or pyrimidine -N-oxide ring group, wherein each of these heteroaromatic ring groups may optionally have 1 to 3 substituents selected from the group consisting of a lower alkyl halogen, phenyl, lower alkoxycarbonyl, amino, lower alkoxy and hydroxy-lower alkyl, with the proviso that said 5- or 6-membered heteroaromatic ring group is not thiazolyl, isothiazolyl, pyridyl or 1,3,5-triazinyl group; or salts thereof. These compounds and salts thereof have anti-inflammatory activity and lipoxygenase-inhibitory activity.
    Type: Grant
    Filed: September 19, 1989
    Date of Patent: October 22, 1991
    Assignee: Otsuka Pharmaceutical Factory, Inc.
    Inventors: Kenichi Kanai, Kiyoto Goto, Kinji Hashimoto
  • Patent number: 5051421
    Abstract: Benzo[b]thiophene derivatives of formula ##STR1## their tautomers and salts, in which the index n is 0, 1 or 2, alk is lower alkylene, Ar is phenyl, naphthyl or a monocyclic, five- or six-membered heteroaryl radical, wherein the aromatic radical is unsubstituted or is mono- or poly-substituted by lower alkyl, halo-lower alkyl, halogen and/or by nitro, and the ring A is unsubstituted or is mono- or poly-substituted by lower alkyl, lower alkoxy, lower alkylthio, lower alkanesulfinyl, lower alkanesulfonyl, halo-lower alkyl, halogen and/or by nitro, can be used, for example, as active ingredients in medicaments.
    Type: Grant
    Filed: January 18, 1990
    Date of Patent: September 24, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Pier G. Ferrini
  • Patent number: 4996316
    Abstract: A process for the preparation of tertiary N,N-dimethylamines by the reaction of primary amines, formaldehyde, and hydrogen under pressure and at elevated temperature in the presence of a nickel-containing hydrogenation catalyst in the liquid phase. The hydrogenation catalyst is suspended in a solvent, the nickel concentration is 0.1 to 10% by weight, based on the primary amine. The starting materials are separate from each other, brought to 80.degree. to 150.degree. C. and 1 to 15 MPa and fed into the catalyst suspension simultaneously with stirring and reacted in one step to form the tertiary N,N-dimethylamines.
    Type: Grant
    Filed: December 24, 1988
    Date of Patent: February 26, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jurgen Weber, Detlef Kampmann, Claus Kniep
  • Patent number: 4927822
    Abstract: There are described compounds of formula I, ##STR1## in which Y is S, O or NR.sub.9,n is 0 or 1,R.sub.9 is hydrogen or alkyl C 1 to 10,R.sub.3 is hydrogen, alkyl C 1 to 10, cycloalkyl C3 to 10, CF.sub.3, SR.sub.10, a 5 or 6 membered heterocyclic group containing one or more S, O or N atoms, NR.sub.4 R.sub.5, phenyl or phenylalkyl C7 to 12, the phenyl, phenylalkyl and heterocyclic groups optionally being fused to a further phenyl group, the heterocyclic group and any phenyl group optionally being substituted by alkyl C 1 to 6, halogen, alkoxy C 1 to 6, nitro, nitrile, CF.sub.3, SR.sub.6, NR.sub.7 R.sub.11 or hydroxy,R.sub.6, R.sub.7 and R.sub.11, which may be the same or different, are each hydrogen or alkyl C 1 to 10,R.sub.4 and R.sub.5, which may be the same or different, are each hydrogen, alkyl C 1 to 10 or phenyl,R.sub.10 is alkyl C 1 to 10,X.sub.1 is S or O, andA is a chain comprising from 2-16 atoms, which chain carries an O or S containing substitutent at a position 2-6 atoms away from the group C=X.
    Type: Grant
    Filed: August 27, 1986
    Date of Patent: May 22, 1990
    Assignee: Fisons plc
    Inventors: Roger C. Brown, John Dixon, David H. Robinson
  • Patent number: 4914206
    Abstract: The present invention provides lankacidin derivatives of the formula ##STR1## and procedures for the production thereof. The lankacidin derivatives [1] show excellent antimicrobial activities and thus can be used for prophylaxis and treatment of infectious disease in animals.
    Type: Grant
    Filed: December 15, 1988
    Date of Patent: April 3, 1990
    Assignee: Takeda Chemical Industries, LTD.
    Inventors: Isao Minamida, Naoto Hashimoto
  • Patent number: 4912224
    Abstract: An antibacterial 7beta-(carboxyalkenoyl)amino-3-cephem-4-carboxylic acid represented by the following formula: ##STR1## (wherein R is aryl or a heterocyclic group;R.sup.1 is hydrogen or halogen;R.sup.2 is a single bond, alkylene, or thiaalkylene;R.sup.3 is a hydrogen atom or carboxy modifying group;R.sup.4 is hydrogen or methoxy;R.sup.5 is hydrogen or a 3-substituent of cephalosporins;R.sup.6 is a hydrogen atom or carboxy modifying group; andX is oxygen, sulfur, or sulfinyl)a pharmaceutical composition containing the same, and a method for treating a bacterial infection with the same.
    Type: Grant
    Filed: December 9, 1987
    Date of Patent: March 27, 1990
    Assignee: Shionogi & Co., Ltd.
    Inventor: Yoshio Hamashima
  • Patent number: 4911745
    Abstract: Novel herbicides are 3-(substituted) phenyl-2-(substituted imino)-1,3,4-dihydrothiadiazoles. Also disclosed are intermediates for such compounds, and processes for producing the herbicidal compounds and their intermediates.
    Type: Grant
    Filed: July 8, 1988
    Date of Patent: March 27, 1990
    Assignee: ICI Americas Inc.
    Inventor: Raymond A. Felix
  • Patent number: 4904660
    Abstract: Novel compounds of the following formula (I) and their salts: A compound of the formula (I) ##STR1## These compounds are expected to be useful for renin inhibitors. Thus, the compounds are useful medical agents, in particular, anti-hypertensive agents.
    Type: Grant
    Filed: February 25, 1988
    Date of Patent: February 27, 1990
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Kohji Nakano, Takashi Fujikura, Ryuichiro Hara, Masato Ichihara, Yukiko Fukunaga, Masayuki Shibasaki
  • Patent number: 4898943
    Abstract: Novel tricyclic triazolopyrimidine compounds represented by formula (I) shown in the specification and physiologically acceptable salts thereof are disclosed. These compounds have an excellent anti-allergic activity and are useful for treatment and prophylaxis of allergic diseases.
    Type: Grant
    Filed: February 8, 1988
    Date of Patent: February 6, 1990
    Assignee: Daiichi Seiyaku Co., Ltd.
    Inventors: Sumiro Isoda, Shunzo Aibara, Tamotsu Miwa, Hiroyuki Fujiwara, Shuichi Yokohama, Hiroo Matsumoto
  • Patent number: 4889553
    Abstract: Herbicidal triazole sulphonamides of the formula: ##STR1## and salts thereof, where: R.sup.1 represents hydrogen or a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl, acyl, alkoxycarbonyl, aminocarbonyl, sulphonyl or heterocyclic group;R.sup.2 represents hydrogen, halo, cyano, hydroxy, mercapto, a substituted or unsubstituted alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, acyl, alkoxycarbonyl, aminocarbonyl, aryl or amino group, or a heterocyclic group;R.sup.3 represents a substituted or unsubstituted heterocyclic, benzheterocyclic, aryl or aralkyl group; andR.sup.4 represents hydrogen, a substituted or unsubstituted alkyl, alkenyl, alkynyl, acyl, aroyl, alkylsulphonyl, alkoxycarbonyl, aminocarbonyl, aralkyl, or a group of the formula: ##STR2## where R.sup.1 and R.sup.2 are as defined hereinbefore, processes for their preparation and compositions containing them.
    Type: Grant
    Filed: May 15, 1987
    Date of Patent: December 26, 1989
    Assignee: Schering Agrochemicals
    Inventors: Graham P. Rowson, John C. Head, Jurgen Westermann, Martin Kruger, Friedrich Arndt, Richard Rees
  • Patent number: 4868183
    Abstract: Disclosed are compounds of the formula ##STR1## wherein: R.sup.1 is a lower alkyl group;R.sup.2 and R.sup.3 are each hydrogen or lower alkyl or R.sup.2 and R.sup.3 taken together may form --(CH.sub.2 (.sub.4)-- or --CH.dbd.CH--CH.dbd.CH--;.alpha. is a 5- or 6-membered heteroaromatic ring group containing 1 to 3 hetero-atoms selected from the group consisting of nitrogen, oxygen and sulfur, or a pyrazine-N-oxide ring, pyridazine-N-oxide ring or pyrimidine-N-oxide ring group, wherein each of these heteroaromatic ring groups may optionally have 1 to 3 substituents selected from the group consisting of a lower alkyl, halogen, phenyl, lower alkoxycarbonyl, amino, lower alkoxy and hydroxy-lower alkyl, with the proviso that said 5- or 6-membered heteroaromatic ring group is not thiazolyl, isothiazolyl, pyridyl or 1,3,5-triazinyl group; or salts thereof. These compounds and salts thereof have anti-inflammatory activity and lipoxygenase-inhibitory activity.
    Type: Grant
    Filed: July 20, 1987
    Date of Patent: September 19, 1989
    Assignee: Otsuka Pharmaceutical Factory, Inc.
    Inventors: Kenichi Kanai, Kiyoto Goto, Kinji Hashimoto
  • Patent number: 4855310
    Abstract: 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: Grant
    Filed: March 25, 1988
    Date of Patent: August 8, 1989
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Kiyoshi Murase, Toshiyasu Mase, Hiromu Hara, Kenichi Tomioka
  • Patent number: 4846984
    Abstract: Disclosed herein is the reaction product of 5-amino-2-mercapto-1,3,4-thiadiazole with hydrocarbyl epoxides. The resulting reaction product finds use as an additive in lubricating oil compositions.
    Type: Grant
    Filed: May 2, 1988
    Date of Patent: July 11, 1989
    Assignee: Mobil Oil Corporation
    Inventors: Angeline B. Cardis, Robert H. Davis, Alfred B. Piotrowski
  • Patent number: 4835168
    Abstract: Compounds of formula (I) ##STR1## wherein R.sup.1 is hydrogen, and R.sup.2 is cyano or --C(.dbd.S)--NH--R.sup.3 ; orR.sup.1 and R.sup.2 taken together are .dbd.C(NH.sub.2).sub.2 or .dbd.C(R.sup.5)(NHR.sup.3 ');R.sup.3 and R.sup.3 ' are hydrogen or --COOR.sup.4 ;R.sup.4 is C.sub.1 -C.sub.10 alkyl, substituted C.sub.1 -C.sub.10 alkyl, C.sub.2 -C.sub.10 alkenyl, substituted C.sub.2 -C.sub.10 alkenyl, phenyl, or substituted phenyl; andR.sup.5 is hydrogen or --S--R.sup.6 where R.sup.6 is C.sub.1 -C.sub.4 alkyl, cyano-C.sub.1 -C.sub.4 alkyl or pyridyl-C.sub.1 -C.sub.4 alkyl, and salts thereof, are useful antiviral agents.
    Type: Grant
    Filed: March 9, 1988
    Date of Patent: May 30, 1989
    Assignee: Eli Lilly and Company
    Inventors: Charles J. Paget, Jr., Brent J. Rieder, Wayne A. Spitzer, Chyun-Yeh E. Wu
  • Patent number: 4831032
    Abstract: The present invention provides benzimidazoles of the general formula: ##STR1## wherein R.sub.1, X, A, and R.sub.2 are as defined in the specification. The present invention also provides processes for the preparation of these new benzimidazoles and pharmaceutical compositions containing them, as well as intermediates for the preparation thereof.The new benzimidazoles are useful to treat heart or circulatory diseases which respond to a lowering of blood pressure, a positive inotropic action and/or an improvement in microcirculation.
    Type: Grant
    Filed: July 3, 1986
    Date of Patent: May 16, 1989
    Assignee: Boehringer Mannheim GmbH
    Inventors: Wolfgang von der Saal, Alfred Mertens, Herbert Berger, Bernd Muller-Beckmann, Klaus Strein
  • Patent number: 4803211
    Abstract: This invention relates to novel heterocyclic compounds structurally characterized by containing a specific heterocyclic group and by the presence of --CH.sub.2 --S-- directly bound to the specific heterocyclic group. These heterocyclic compounds are useful as medicines, particularly as antagonists of SRS-A (slow reacting substance of anaphylaxis).
    Type: Grant
    Filed: July 14, 1986
    Date of Patent: February 7, 1989
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Toshiyasu Mase, Ryuji Tsuzuki, Hiromu Hara, Kiyoshi Murase, Kenichi Tomioka
  • Patent number: 4803277
    Abstract: Novel insecticidally active heterocyclic compounds of the formula ##STR1## wherein W represents a substituted pyridyl group, or a 5- or 6-membered optionally substituted heterocyclic group containing at least two hetero atoms selected from oxygen, sulfur and nitrogen atoms,R represents a hydrogen atom or an alkyl group,Y represents .dbd.N--or ##STR2## R' represents a hydrogen atom, an alkyl group, an aryl group, an acyl group, an alkoxycarbonyl group or a cyano group,Z represents a nitro group or a cyano group, andT represents 3 or 4 optionally substituted ring members of a 5- or 6-membered unsaturated heterocyclic ring which it forms together with the adjoining carbon atom and nitrogen atom, said 5- or 6-membered unsaturated heterocyclic ring containing 1 to 3 hetero atoms which are selected from oxygen, sulfur and nitrogen atoms and at least one of which is a nitrogen atom.
    Type: Grant
    Filed: August 24, 1987
    Date of Patent: February 7, 1989
    Assignee: Nihon Tokushu Noyaku Seizo K.K.
    Inventors: Kozo Shiokawa, Shinichi Tsuboi, Shoko Sasaki, Koichi Moriya, Yumi Hattori, Katsuhiko Shibuya
  • Patent number: 4786627
    Abstract: Thiadiazole guanidines of formula 1 ##STR1## wherein R is hydrogen or C.sub.1-4 alkyl and their non-toxic salts. Processes for their preparation and pharmaceutical compositions thereof. The compounds exhibit anti-convulsant activity and are indicated for use in the treatment of epilepsy.
    Type: Grant
    Filed: April 8, 1988
    Date of Patent: November 22, 1988
    Assignee: Reckitt & Colman Products Limited
    Inventors: Stephen Turner, Malcolm Myers
  • Patent number: 4762848
    Abstract: Heterocyclic sulfides of the general formula heterocycle-S-R, a process for their preparation and, in particular, their use for immunostimulation, immunorestoration and cytostatic treatment, and pharmaceutical agents, which contain a sulfide of this type, for these indications.
    Type: Grant
    Filed: March 10, 1986
    Date of Patent: August 9, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Karl-Heinz Scheunemann, Walter Durckheimer, Jurgen Blumbach, Michael Limbert, Hans-Ulrich Schorlemmer, Gerhard Dickneite, Hans-Harald Sedlacek
  • Patent number: 4746669
    Abstract: Thiazole derivatives have been made, for example, by reacting a 2-aryl-2,2-dialkoxyethylamine with an appropriately substituted aryl acetyl halide followed by treating the resulting amide with diphosphoryl pentasulfide. The thiazole derivatives are found to be effective immunoregulants.
    Type: Grant
    Filed: March 26, 1987
    Date of Patent: May 24, 1988
    Assignee: Merck & Co., Inc.
    Inventors: Charles G. Caldwell, Ihor Kopka, Milton L. Hammond, Robert A. Zambias
  • Patent number: 4742060
    Abstract: Novel insecticides of the formula ##STR1## in which n is 0 or 1,X is S, O, ##STR2## Y is N or ##STR3## Z is a 5- or 6-membered nitrogen-containing heterocyclic ring, and R to R.sup.9 variously represent hydrogen or specified organic radicals.
    Type: Grant
    Filed: January 21, 1986
    Date of Patent: May 3, 1988
    Assignee: Nihon Tokushu Noyaku Seizo K. K.
    Inventors: Kozo Shiokawa, Shinichi Tsuboi, Shinzo Kagabu, Koichi Moriya
  • Patent number: 4727081
    Abstract: 3,4-Diazole derivatives corresponding to the general formula I ##STR1## which exert a highly selective action on histamine-H.sub.2 receptors are described. Processes for the preparation of these compounds and pharmaceutical preparations containing these compounds are also described.
    Type: Grant
    Filed: November 7, 1985
    Date of Patent: February 23, 1988
    Assignee: Ludwig Heumann & Co. GmbH
    Inventors: Kurt Wegner, Irene Kramer, Helmut Schickaneder, Walter Schunack, Istvan Szelenyi, Kurt H. Ahrens
  • Patent number: 4722934
    Abstract: The present invention relates to a thiadiazole derivative of the following general formula (I) and an insecticidal and miticidal composition containing the same as an active ingredient: ##STR1## wherein A represents a group of the formula ##STR2## R.sup.1 and R.sup.2 independently represent a hydrogen atom, a halogen atom, a lower alkyl group, a trifluoromethyl group, a cyano group or a nitro group or jointly represent a methylenedioxy group, R.sup.3 represents a hydrogen atom or a lower alkyl group, R.sup.4 represents a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a monoalkylamino group having a lower alkyl group or a dialkylamino group having lower alkyl group, and n is an integer of from 1 through 3.
    Type: Grant
    Filed: March 16, 1987
    Date of Patent: February 2, 1988
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Susumu Matsumoto, Shigeru Suzuki, Hiroki Ohta, Yoshiaki Higashino, Toshiki Fukuchi
  • Patent number: 4703125
    Abstract: A carbonyl compound of the formula ##STR1## in which R.sup.1 denotes hydrogen, aryl, substituted aryl or a straight-chain or cyclic, saturated or unsaturated aliphatic hydrocarbon radical, which is optionally interrupted by O, S, N, N-alkyl, N-aryl or N-aralkyl, and which is optionally substituted by hydroxyl, alkoxy, alkyl, trifluoromethyl, halogen, phenyl, alkoxycarbonyl or dialkylamino, the two alkyl radicals together with the nitrogen atom optionally forming a 5 to 7-membered ring, which optionally contains a heteroatom from the group comprising O, S, NH or N-alkyl and these aforementioned alkyl and phenyl radicals in turn optionally being substituted by halogen, trifluoromethyl, alkyl, aryl, aralkyl, alkoxy, alkylmercapto or SO.sub.2 -alkyl,R.sup.2 represents the radical CXR.sup.8, R.sup.8 having the meaning indicated for R.sup.1 and being identical to or different from R.sup.1, and X representing oxygen, sulphur or the radical NR.sup.9 R.sup.10, R.sup.9 and R.sup.
    Type: Grant
    Filed: July 1, 1986
    Date of Patent: October 27, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Axel Ingendoh, Horst Meyer, Bernward Garthoff
  • Patent number: 4695567
    Abstract: The present invention provided pyrrolobenzimidazoles or tautomer thereof, of the general formula: ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl or C.sub.3 -C.sub.7 cycloalkyl;R.sub.2 is hydrogen, cyano, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, or a carbonyl group substituted by hydroxyl, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkyoxy, amino, C.sub.1 -C.sub.6 alkylamino, C.sub.2 -C.sub.12 dialkylamino or hydrazino, orR.sub.2 and R.sub.1 together with the carbon to which they are attached form a C.sub.3 -C.sub.8 spirocycloalkyl ring, or R.sub.1 and R.sub.2 together form C.sub.3 -C.sub.7 alkylidene or C.sub.3 -C.sub.7 cycloalkylkidene,X is a valency bond, C.sub.1 -C.sub.
    Type: Grant
    Filed: January 17, 1986
    Date of Patent: September 22, 1987
    Assignee: Boehringer Mannheim GmbH
    Inventors: Alfred Mertens, Jens-Peter Holck, Herbert Berger, Bernd Muller-Beckmann, Klaus Strein, Egon Roesch
  • Patent number: 4648897
    Abstract: Compounds of the formula ##STR1## wherein Ar is aryl, R.sup.1 is halomethyl, R.sup.2 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, haloalkyl, alkylthio, alkenylthio, alkynylthio, aryl or NR.sup.5 R.sup.6 wherein R.sup.5 and R.sup.6 individually are hydrogen, alkyl, alkenyl or alkynyl, R.sup.3 is hydrogen or alkyl, n is 1 or 2, Y is O, S or NR wherein R is hydrogen, alkyl, alkenyl or alkynyl, have been found to be useful herbicides. The compounds are prepared by acylation of the corresponding N-heterocyclealkylene-N-arylamine.
    Type: Grant
    Filed: July 21, 1980
    Date of Patent: March 10, 1987
    Assignee: Chevron Research Company
    Inventor: David C. K. Chan
  • Patent number: 4645841
    Abstract: Compounds of the tautomeric formula ##STR1## wherein R, R.sub.1 and R.sub.2, which may be identical to or different from each other, are each hydrogen or alkyl of 1 to 4 carbon atoms;R.sub.3 is straight or branched alkyl, optionally interrupted by heteroatoms such as oxygen, sulfur or nitrogen; straight or branched alkenyl; alkynyl; cyano; cycloalkyl or cycloaliphatic alkyl; a bicyclic group; aryl; or a heterocyclic group; orR.sub.2 and R.sub.3, together with each other and the nitrogen atoms to which they are attached, form a heterocyclic group;R.sub.4 is hydrogen, halogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms; andHet is a substituted or unsubstituted heterocycle containing two or three heteroatoms; tautomers thereof, and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful as anti-ulcerogenics.
    Type: Grant
    Filed: June 24, 1985
    Date of Patent: February 24, 1987
    Assignee: Istituto de Angeli, S.p.A.
    Inventors: Giuseppe Bietti, Enzo Cereda, Arturo Donetti, Piero Del Soldato, Antonio Giachetti, Rosamaria Micheletti
  • Patent number: 4642132
    Abstract: Aminothiadiazoles of the formula ##STR1## where R.sup.1, R.sup.2, A, X, Z, m and n have the meanings given in the description, are used for controlling undesirable plant growth.
    Type: Grant
    Filed: December 26, 1984
    Date of Patent: February 10, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulrich Schirmer, Peter Plath, Hubert Sauter, Bruno Wuerzer
  • Patent number: 4617389
    Abstract: Antineoplastic compounds of the formula, IIa, ##STR1## wherein: Y is hydrogen or lower alkyl; and Z is a lower alkoxy substituted quinolinylamino radical, a cyano substituted pyrazolylamino radical or a mono- or di-lower alkyl substituted thiazolamino radical, ora nitrogen-containing heterocyclic radical, ora cyano, phenyl, carboxamido or lower alkoxycarbonyl substituted 1-aziridinyl radical ora lower alkyl, formyl or acetylphenyl substituted 1-piperazinyl radical, oran hydroxy or piperidyl substituted 1-piperidyl radical, ora lower alkoxy, amino or halo substituted pyridylamino radical, ora carboxamido, mercapto or methylenedioxy substituted anilino radical, ora radical of the formula, ##STR2## wherein R is hydrogen or lower alkyl and R" is a nitrogen-containing heterocyclic radical, ora butyrolactonyl radical, oran adamantyl radical, ora mono- lower alkoxy substituted phenyl radical, ora substituted lower alkyl radical selected from the group consisting of mercapto lower alkyl, carboxy lower alkyl, mono-, d
    Type: Grant
    Filed: December 15, 1983
    Date of Patent: October 14, 1986
    Assignee: University Patents, Inc.
    Inventor: William A. Remers
  • Patent number: 4606755
    Abstract: This invention relates to ortho-(isoxazolyl, isothiazolyl, pyrazolyl, thiadiazolyl, oxadiazolyl, and triazolyl)benzenesulfonamides and their use as herbicides.
    Type: Grant
    Filed: December 21, 1984
    Date of Patent: August 19, 1986
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Morris P. Rorer
  • Patent number: 4607043
    Abstract: Tetrahydro-3,5-dioxo-1H-pyrrolizine-7a(5H)-alkanoic acids, base addition salts, esters, and amides are useful as agents for the reversal of amnesia. Pharmaceutical compositions containing said compounds and methods for using said compositions for treating senility and reversal of amnesia are also taught.
    Type: Grant
    Filed: June 28, 1985
    Date of Patent: August 19, 1986
    Assignee: Warner-Lambert Company
    Inventor: Donald E. Butler
  • Patent number: 4604132
    Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: A, B and D are selected from CH and N;E is selected from oxygen and sulfur;X are selected from halogen, nitro, cyano, alkyl, substituted alkyl, hydroxy, alkoxy, substituted alkoxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, acyloxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, sulfamoyl, substituted sulfamoyl, alkanoyloxy, benzyloxy, substituted benzyloxy, phenyl, substituted phenyl, amino, substituted amino, and the groups formyl and alkanoyl and the oxime, imine and Schiff base derivatives thereof;R.sup.1 is selected from hydrogen, alkyl, alkenyl, alkynyl, substituted alkyl, alkylsulfonyl, arylsulfonyl, acyl and an inorganic or organic cation;R.sup.2 is selected from alkyl substituted alkyl, alkenyl, haloalkenyl, alkynyl and haloalkynyl;R.sup.3 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl, and phenyl;R.sup.
    Type: Grant
    Filed: April 27, 1984
    Date of Patent: August 5, 1986
    Assignee: ICI Australia Limited
    Inventors: Richard J. Conway, Keith G. Watson, Graeme J. Farquharson
  • Patent number: 4578470
    Abstract: Phthalimides and the like in which the substituent on the imide nitrogen is a highly electron-deficient group may be prepared by the reaction of the appropriate amine with phthalic anhydride. These imides are useful for the preparation of polyimides by reaction with diamines.
    Type: Grant
    Filed: June 20, 1983
    Date of Patent: March 25, 1986
    Assignee: General Electric Company
    Inventor: Jimmy L. Webb
  • Patent number: 4569996
    Abstract: This invention provides a process for the preparation of pyrimidinone compounds with a group R.sup.2 CH(OH)-- at the 5-position thereof, wherein R.sup.2 is an optionally substituted acid-stable 5- or 6-membered nitrogen-containing heteroaryl group. The pyrimidinone ring is further substituted by a side-chain of a H.sub.1 -antagonist or H.sub.2 -antagonist or a precursor thereof.The compounds are convertible to 5-heteroaryl methyl compounds which are either useful H.sub.1 - or H.sub.2 -antagonists or precursors thereof.
    Type: Grant
    Filed: July 27, 1983
    Date of Patent: February 11, 1986
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: John Kitteringham, Brian P. Slingsby
  • Patent number: 4562260
    Abstract: An improved process for the production of certain 1,3,4-thiadiazole-5-sulfonamides, specifically the precursor to 5-[[(dimethylamino)-carbonyl]methylamino]-N,N-dimethyl-1,3,4-thiadiazole-2 -sulfonamide.
    Type: Grant
    Filed: July 3, 1984
    Date of Patent: December 31, 1985
    Assignee: Union Carbide Corporation
    Inventors: Roger L. McDaniel, Jr., Jeffrey W. Portzer, Edward J. Zaiko
  • Patent number: 4554357
    Abstract: Bis-quaternary ammonium and phosphonium salts such as bis(tri-n-butyl)-1,6-hexylenediammonium dibromide are excellent phase transfer agents for the preparation of aromatic ether imides, as by the reaction of the disodium salt of bisphenol A with 4-nitro-N-methylphthalimide.
    Type: Grant
    Filed: October 14, 1983
    Date of Patent: November 19, 1985
    Assignee: General Electric Company
    Inventors: John W. Verbicky, Jr., Elbridge A. O'Neil, Jr.
  • Patent number: 4548944
    Abstract: Compounds of the tautomeric formula ##STR1## wherein R, R.sub.1 and R.sub.2, which may be identical to or different from each other, are each hydrogen or alkyl of 1 to 4 carbon atoms;R.sub.3 is straight or branched alkyl, optionally interrupted by heteroatoms such as oxygen, sulfur or nitrogen; straight or branched alkenyl; alkynyl; cyano; cycloalkyl or cycloaliphatic alkyl; a bicyclic group; aryl; or a heterocyclic group; orR.sub.2 and R.sub.3, together with each other and the nitrogen atoms to which they are attached, form a heterocyclic group;R.sub.4 is hydrogen, halogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms; andHet is a substituted or unsubstituted heterocycle containing two or three heteroatoms;tautomers thereof, and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful as anti-ulcerogenics.
    Type: Grant
    Filed: February 10, 1983
    Date of Patent: October 22, 1985
    Assignee: Istituto de Angeli S.p.A.
    Inventors: Giuseppe Bietti, Enzo Cereda, Arturo Donetti, Piero del Soldato, Antonio Giachetti, Rosamaria Micheletti
  • Patent number: 4547579
    Abstract: There are described novel dyes of the formulae ##STR1## in which R.sub.1 and R.sub.2 independently of one another are each hydrogen, unsubstituted or substituted alkyl, cycloalkyl, aralkyl or aryl, and R.sub.1 and R.sub.2 together with the nitrogen atom, and optionally with the inclusion of further hetero atoms, can also form a 5- to 7-membered heterocycle, or one of the radicals R.sub.1 or R.sub.2 can be linked with the carbon atoms, in the o-position with respect to the amino group, of the ring A to form a fused-on, saturated, unsubstituted or substituted 5- or 6- membered ring,X is .dbd.NR.sub.3, .dbd.NCOR.sub.4, ##STR2## .dbd.NH or .dbd.O, wherein R.sub.3 is alkyl or unsubstituted or substituted phenyl,R.sub.4 is unsubstituted or substituted alkyl, aralkyl, aryl, vinyl, alkoxy, phenoxy or amino, andR.sub.5 is cyano, carbalkoxy, or unsubstituted or substituted carbonamide, andR.sub.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: October 15, 1985
    Assignee: Ciba-Geigy Corporation
    Inventor: Peter Mockli
  • Patent number: 4540699
    Abstract: This invention relates to N-substituted pyridinone compounds which have histamine H.sub.2 -antagonist activity. A specific compound of this invention is 2-[2-(5-methyl-4-imidazolylmethylthio)ethylamino]-5-(1-methyl-2-oxopyridin -4-ylmethyl)pyrimidin-4-one.
    Type: Grant
    Filed: November 29, 1983
    Date of Patent: September 10, 1985
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Thomas H. Brown, Derek A. Rawlings
  • Patent number: 4536189
    Abstract: An anti-corrosion additive composition for motor fuels containing a minor amount (i.e., from 1 to 10%) of a short chain aliphatic alcohol that is prepared by reacting substantially equal molar amounts of maleic anhydride and a hydrocarbon-substituted mono primary amine or hydrocarbon-substituted mono primary ether amine to produce a maleamic acid intermediate reaction product followed by (b) reacting said intermediate product of (a) with a substantially equal molar amount of a heterocyclic selected from the group consisting of 5-amino-1,3,4-thiadiazole-2-thiol or benzotriazole, said hydrocarbon-substituted mono primary amine being represented by the formula:R--NH.sub.
    Type: Grant
    Filed: April 27, 1984
    Date of Patent: August 20, 1985
    Assignee: Texaco Inc.
    Inventor: Rodney L. Sung
  • Patent number: 4465504
    Abstract: An N-(2,2,2-trifluoroethyl)-N-alkyl-azolyloxyacetic acid amides of the formula ##STR1## in which R and R.sup.1 have the meaning given in the description, a process for the production of which is described, find use as herbicides. The intermediate products of the general formulae ##STR2## in which R.sup.1 in each case has the same meaning as in formula (I), for the preparation of the compounds (I) are also new.
    Type: Grant
    Filed: February 19, 1982
    Date of Patent: August 14, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz Forster, Volker Mues, Bernd Baasner, Hermann Hagemann, Ludwig Eue, Robert Schmidt
  • Patent number: 4464374
    Abstract: The invention relates to a guanidine derivative of the formula: ##STR1## in which W is a 2-6C alkylene chain optionally substituted by 1 or 2 1-4C alkyls; E is O, S, SO, SO.sub.2 or NR.sup.3 in which R.sup.3 is H or 1-6C alkyl; R.sup.1 is H or a straight chain 1-6C alkyl optionally substituted by 1 or 2 1-4C alkyls; or R.sup.1 and R.sup.3 are joined to form a morpholine, pyrrolidine, piperidine or piperazine ring; X, P, Y, Q and R.sup.2 are as defined in the specification, and the pharmaceutically-acceptable acid-addition salts thereof. Manufacturing process, pharmaceutical compositions and intermediates are also described. The compounds of the formula I are histamine H-2 antagonists.
    Type: Grant
    Filed: July 23, 1981
    Date of Patent: August 7, 1984
    Assignees: ICI Americas Inc., Imperial Chemical Industries PLC
    Inventors: Tobias O. Yellin, David J. Gilman, Derrick F. Jones, Keith Oldham
  • Patent number: 4440775
    Abstract: The compounds are novel N-substituted-N'-heterocyclic alkylthioureas, guanidines and 1-nitro-2,2-diaminoethylene compounds which are histamine H.sub.2 -antagonists.
    Type: Grant
    Filed: June 18, 1982
    Date of Patent: April 3, 1984
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Graham J. Durant, Charon R. Ganellin, Geoffrey R. Owen, Rodney C. Young
  • Patent number: 4423053
    Abstract: Compounds which are derivatives of 2-amino-5-(o-sulphamidophenyl)-1,3,4-thiadiazol of formula ##STR1## wherein R is a hydrogen atom or a --CH.sub.3, --C.sub.2 H.sub.5, iso--C.sub.3 H.sub.7, n--C.sub.4 H.sub.9 or --CH.sub.2 --CH.dbd.CH.sub.2 group and R.sub.1 is a hydrogen atom or a --CH.sub.3 or --C.sub.2 H.sub.5 group, are active agents against virus infections in higher animal organisms.
    Type: Grant
    Filed: March 16, 1982
    Date of Patent: December 27, 1983
    Assignee: Societa Italo-Britannica L. Manetti-H. Roberts & Co.
    Inventor: Giovanni Orzalesi
  • Patent number: 4412079
    Abstract: Novel thiadiazole compounds are disclosed which contain in the 5 position, C-linked moieties which are either acyclic hydrocarbon radicals or halogenated acyclic hydrocarbon radicals (in which case each halogen is independently selected from F, Cl and Br). These novel compounds also contain an exocyclic nitrogen in the 2 position, and some of them contain the exocyclic substituent: ##STR1## wherein R.sub.3 is a lower acyclic hydrocarbon radical and R.sub.4 is either H or a lower acyclic hydrocarbon radical. Synthesis of these compounds is disclosed, including synthesis of those which exhibit isomerism and/or tautomerism.Various of these compounds have various agricultural utilities (e.g. as herbicides, insecticides, acaricides and fungicides), each of them having at least one such biological utility. Methods of using these compounds in phytotoxic fungicidal, acaricidal and insecticidal applications are disclosed.
    Type: Grant
    Filed: September 20, 1982
    Date of Patent: October 25, 1983
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Tony Cebalo, Robert A. Walde
  • Patent number: 4388319
    Abstract: The compounds are N,N'-substituted thioureas, ureas and guanidines which are H-2 histamine receptor inhibitors. A compound of this invention is N-cyano-N'-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]-N"-[2-(2-thiazolyl methylthio)ethyl]guanidine.
    Type: Grant
    Filed: December 11, 1980
    Date of Patent: June 14, 1983
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Graham J. Durant, Charon R. Ganellin