Amidine, Azomethine, Ketimine Or Oxime In Acid Moiety Patents (Class 560/35)
  • Patent number: 5646183
    Abstract: This invention relates to phenyl amidine alkanoic acids and lactones having the following formula ##STR1## or a pharmaceutically acceptable salt which are useful in the inhibition of platelet aggregation. This invention also relates to pharmaceutical compositions of such phenyl amidine derivatives.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: July 8, 1997
    Assignee: G. D. Searle & Co.
    Inventors: Norman Anthony Abood, Robert Everett Manning, Masateru Miyano
  • Patent number: 5625093
    Abstract: Novel substituted amino acid derivatives are provided which inhibit platelet aggregation and which are useful in pharmaceutical compositions and methods of inhibiting platelet aggregation.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: April 29, 1997
    Assignee: G. D. Searle & Co.
    Inventor: Thomas E. Rogers
  • Patent number: 5618775
    Abstract: Mixtures of optically active cyclohexenone oxime ethers having R- and S-configuration in the oxime ether moiety of the formula I ##STR1## (R.sup.1 =C.sub.1 -C.sub.6 -alkyl; ##STR2## X=C.sub.1-C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl; m=0-3 or 1-4 where all X's are halogen;n=0-3 or 1-5 where all X's are halogen;R.sup.2 =C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkylthio-C.sub.1 -C.sub.6 -alkyl, substituted or unsubstituted C.sub.3 -C.sub.7 -cycloalkyl, substituted or unsubstituted C.sub.5 -C.sub.7 -cycloalkenyl, substituted or unsubstituted 5-membered saturated heterocyclic structure, substituted or unsubstituted 6- or 7-membered heterocyclic structure, substituted or unsubstituted 5-membered heteroaromatic structure, substituted or unsubstituted phenyl or pyridyl)and their agriculturally useful salts and esters with C.sub.1 -C.sub.10 -carboxylic acids and inorganic acids.
    Type: Grant
    Filed: August 11, 1994
    Date of Patent: April 8, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulf Misslitz, Norbert Meyer, Juergen Kast, Wolfgang Ladner, Helmut Walter, Karl-Otto Westphalen, Uwe Kardorff, Matthias Gerber
  • Patent number: 5616778
    Abstract: The compound of the formula ##STR1## having the following CIELAB values: L*=82.55a*=11.53b*=90.49C*=91.22 andH*=82.74.
    Type: Grant
    Filed: April 21, 1994
    Date of Patent: April 1, 1997
    Assignee: Sandoz Ltd.
    Inventors: J urgen Goldmann, Bansi L. Kaul
  • Patent number: 5616615
    Abstract: The present invention concerns enaminones having the formula: ##STR1## wherein R is COOCH.sub.3 ; R.sup.1 is CH.sub.3 ; R.sup.2 is H; and R.sup.3 is selected from the group consisting of C.sub.6 H.sub.4 (p-Cl) and CH.sub.2 C.sub.6 H.sub.5.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: April 1, 1997
    Assignee: Howard University
    Inventors: Kenneth R. Scott, Jesse M. Nicholson, Ivan O. Edafiogho
  • Patent number: 5614539
    Abstract: Novel urea derivatives are provided which inhibit platelet aggregation. This invention also pertains to pharmaceutical compositions and methods of using such derivatives.
    Type: Grant
    Filed: June 1, 1995
    Date of Patent: March 25, 1997
    Assignee: G. D. Searle & Co.
    Inventors: Steven P. Adams, Foe S. Tjoeng, Mark E. Zupec
  • Patent number: 5614555
    Abstract: Amidinophenol derivatives of the formula (I) ##STR1## wherein the various symbols are as defined herein; which have inhibitory activities on PLA.sub.2 and on various proteases such as trypsin, plasmin, thrombin, kallikrein, especially trypsin, and are useful for the prevention and/or the treatment of various inflammatory diseases, allergic diseases, disseminated intravascular coagulation, pancreatitis, severity in pancreatitis and multiple organ failure.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: March 25, 1997
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Hisao Nakai, Masanori Kawamura, Tsumoru Miyamoto
  • Patent number: 5597825
    Abstract: The invention relates to biphenyl derivatives of general formula ##STR1## wherein A to E and X are defined as in claim 1, the stereoisomers thereof, including their mixtures and the salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, which have valuable properties, preferably aggregation-inhibiting effects, pharmaceutical compositions containing these compounds and processes for preparing them.
    Type: Grant
    Filed: May 16, 1994
    Date of Patent: January 28, 1997
    Assignee: Dr. Karl Thomae GmbH
    Inventors: Frank Himmelsbach, Helmut Pieper, Volkhard Austel, G unter Linz, Thomas M uller, Wolfgang Eisert, Johannes Weisenberger
  • Patent number: 5583249
    Abstract: Compounds of formula I are suitable for controlling and preventing infestation by microorganisms, insects and acarina on plants ##STR1## and their possible isomers and mixtures of isomers, whereina) X is CH.sub.2 F or CHF.sub.2,Y is CH andZ is OCH.sub.3, orb) X is CH.sub.2 F or CHF.sub.2,Y is a nitrogen atom andZ is OCH.sub.3 or NHCH.sub.3,and wherein R.sub.1 and R.sub.2 are each independently of the other hydrogen, cyano, C.sub.1 -C.sub.12 alkyl, halo-C.sub.1 -C.sub.12 alkyl, C.sub.2 -C.sub.12 alkenyl, C.sub.2 -C.sub.12 alkynyl, C.sub.3 -C.sub.6 cycloalkyl, cyclopropylmethyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.12 alkoxyalkyl, C.sub.1 -C.sub.4 alkoxycarbonyl, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: December 10, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Albert Pfifner, Stephen Trah
  • Patent number: 5573999
    Abstract: .beta.-Substituted cinnamic acid derivatives of the formula 1, ##STR1## where R.sup.1 is alkyl, chlorine or bromine, --X-- is --O--, --S--, ##STR2## m is 0 or 1, --Y is --OR.sup.4, --O--N.dbd.CR.sup.5 R.sup.6, --NR.sup.7 R.sup.8, --N(OR.sup.9)R.sup.10 or --SR.sup.11, where the above-mentioned substituents R.sup.2 to R.sup.11 are alkyl, and R.sup.2, and R.sup.3 and R.sup.5 to R.sup.11 can also be hydrogen,Z is halogen, nitro, cyano, alkyl, cycloalkyl, aralkyl, aryloxyalkyl, arylthioalkyl, hetarylalkyl, hetaryloxyalkyl, hetarylthioalkyl, alkenyl, aralkenyl, aryloxyalkenyl, arylthioalkenyl, hetarylalkenyl, hetaryloxyalkenyl, hetarylthioalkenyl, alkynyl, arylalkynyl, hetarylalkynyl, aryl, hetaryl, arylazo, acylamino, --OR.sup.12, --SR.sup.13, --SOR.sup.14, --SO.sub.2 R.sup.15, --COOR.sup.16, --CONR.sup.17 R.sup.18, --COR.sup.19, --CR.sup.20 .dbd.NR.sup.21, --N.dbd.CR.sup.22, R.sup.23, --CR.sup.24 .dbd.N--OR.sup.25, --CR.sup.25 R.sup.26 --O--, N.dbd.CR.sup.27 R.sup.28, --CH.sub.2 --OCOR.sup.39 or --NR.sup.37 R.
    Type: Grant
    Filed: May 15, 1995
    Date of Patent: November 12, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Hubert Sauter, Herbert Bayer, Klaus Oberdorf, Horst Wingert, Wolfgang von Deyn, Wassilios Grammenos, Hartmann Koenig, Harald Rang, Franz Roehl, Gisela Lorenz, Eberhard Ammermann
  • Patent number: 5567411
    Abstract: Dendritic derivatives of 3,5-bis(aminomethyl)benzene and aminomethyl benzene core groups are disclosed. In each derivative, termed an "amplifier" because the dendritic structure on each molecule terminates with multiple termini to each of which an "active group" can be attached, the desired effect of the active group per mole is amplified compared to conventional compounds having only one active group per molecule. Amplifier molecules can include a targeting group permitting the molecules to preferentially attach to a particular anatomical or physiological situs. Active groups are any of various pharmacologically or therapeutically active moieties, including moieties useful for magnetic-resonance contrast enhancement. The dendritic structures comprise linkers and branch groups covalently bonded to each other in any of various structural combinations. The amplifiers can be prepared as a solution or mixture with a physiologically compatible carrier for administration to a warm-blooded animal subject.
    Type: Grant
    Filed: September 29, 1994
    Date of Patent: October 22, 1996
    Assignee: State of Oregon Acting by and Through the State Board of Higher Education on Behalf of the University of Oregon
    Inventors: John F. W. Keana, Vladimir Martin, William H. Ralston
  • Patent number: 5561733
    Abstract: Novel acceptor-donor-acceptor and donor-acceptor-donor compound for use in forming a thermally-stable electro-optic waveguide are disclosed. Also disclosed is a thermally stable waveguide material containing thermally stable acceptor-donor-acceptor or donor-acceptor-donor guest dipole compounds in a temperature-resistant polymer matrix. The waveguide has selected regions in which the net dipoles of the guest molecules are oriented, for electro-optic switching when an electric field is placed across these regions.
    Type: Grant
    Filed: May 8, 1995
    Date of Patent: October 1, 1996
    Assignee: Lockhead Missiles & Space Company, Inc.
    Inventors: Susan P. Ermer, Doris S. Y. Leung, Steven M. Lovejoy
  • Patent number: 5545664
    Abstract: Substituted phenoxymethylphenyl derivatives I ##STR1## X is .dbd.CH--OCH.sub.3, .dbd.C--CH.sub.3 or .dbd.N--OCH.sub.3 ; R.sup.1 is, inter alia,R.sup.2 and R.sup.3 are, inter alia,H, halogen, CN, NO.sub.2, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.2 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 --C.sub.2 -haloalkoxy;R.sup.4 is, inter alia,CN, Cl, Dr, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylthio or C.sub.1 -C.sub.4 -haloalkoxy;R.sup.5 is, inter alia,NO.sub.2, CN, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -haloalkoxy;n is 0-4; Y is --O--, --NH--, --N(CH.sub.3)--; R.sup.6 is H, C.sub.1 -C.sub.4 -alkyl.The compounds are useful for controlling pests and fungi.
    Type: Grant
    Filed: March 23, 1995
    Date of Patent: August 13, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Reinhard Kirstgen, Klaus Oberdorf, Hubert Sauter, Herbert Bayer, Wassilios Grammenos, Harald Rang, Volker Harries, Gisela Lorenz, Eberhard Ammermann
  • Patent number: 5543433
    Abstract: Compounds of the formula I ##STR1## where X is hydrogen, halogen, alkyl, alkoxy, trifluoromethyl, cyano or nitro,Y is an amino, methylamino or dimethylamino group,Z is a group CHCH.sub.3, CHOCH.sub.3 or NOCH.sub.3,R is hydrogen or alkyl,A is hydrogen, alkyl, haloalkyl or cycloalkyl,B is unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl or the group ##STR2## where W is hydrogen, alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, unsubstituted or substituted aryl or heteroaryl, unsubstituted or substituted aryloxy, arylthio, arylamino or aryl-N-(C.sub.1 -C.sub.6 -alkyl)amino, heteroaryloxy, heteroarylthio, heteroarylamino or heteroaryl-N-(alkyl)amino orA and B, together with the C atom whose substituents they are, are an isocyclic or heterocyclic ring which can also be quinonoid,and fungicides containing these compounds.
    Type: Grant
    Filed: June 3, 1994
    Date of Patent: August 6, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Reinhard Doetzer, Hubert Sauter, Herbert Bayer, Franz Roehl, Gisela Lorenz, Eberhard Ammermann, Horst Wingert
  • Patent number: 5536869
    Abstract: The present invention relates to a novel process for the preparation of ethyl 3S-[[4-[[4-(aminoiminomethyl)phenyl]amino]-1,4-dioxobutyl]amino]-4-pentyno ate and pharmaceutically acceptable acid addition salt thereof which comprises treating (trimethylsilyl)acetylene sequentially with n-butyllithium and 4-formylmorpholine followed by acid hydrolysis to give 3-(trimethylsilyl)-2-propynal; treating 3-(trimethylsilyl)-2-propynal with lithium bis(trimethylsilyl)amide to give in situ N,3-bis(trimethylsilyl)-2-propyn-1-imine; condensation of N,3-bis(trimethylsilyl)-2-propyn-1-imine with lithium t-butyl acetate to give (.+-.)1,1-dimethylethyl 3-amino-5-(trimethylsilyl)-4-pentynoate; treating (.+-.)1,1-dimethylethyl 3-amino-5-(trimethylsilyl)-4-pentynoate- with p-toluenesulfonic acid to give (.+-.)1,1-dimethylethyl 3-amino-5-(trimethylsilyl)-4-pentynoate, mono p-toluenesulfonic acid salt, treatment of resulting salt with ethanol in the presence of p-toluenesulfonic acid to give (.+-.
    Type: Grant
    Filed: July 14, 1995
    Date of Patent: July 16, 1996
    Assignee: G. D. Searle & Co.
    Inventors: Kevin A. Babiak, Srinivasan Babu, James R. Behling, Mark L. Boys, Kimberly J. Cain-Janicki, Wendel W. Doubleday, Payman Farid, Timothy J. Hagen, E. Ann Hallinan, Donald W. Hansen, Jr., Donald E. Korte, Kathleen T. McLaughlin, John R. Medich, Sean T. Nugent, Vlasdislav Orlovski, Jung M. Park, Karen B. Peterson, Daniel R. Pilipauskas, Barnett S. Pitzele, Sofya Tsymbalov, Glenn L. Stahl
  • Patent number: 5523302
    Abstract: This invention relates to novel compounds containing basic and acidic termini, pharmaceutical compositions containing such compounds, processes for preparing such compounds, and to methods of using these compounds, alone or in combination with other therapeutic agents, for the inhibition of platelet aggregation, as thrombolytics, and/or for the treatment of thromboembolic disorders.
    Type: Grant
    Filed: November 24, 1993
    Date of Patent: June 4, 1996
    Assignee: The Du Pont Merck Pharmaceutical Company
    Inventors: Gary A. Cain, Charles J. Eyermann
  • Patent number: 5514716
    Abstract: This disclosure relates to a novel class of hydroxamic and carboxylic acid based matrix metalloproteinase inhibitor derivatives. The disclosure further relates to pharmaceutical compositions containing such compounds and to the use of such compounds and compositions in the treatment of matrix metalloproteinase induced diseases.
    Type: Grant
    Filed: February 25, 1994
    Date of Patent: May 7, 1996
    Assignee: Sterling Winthrop, Inc.
    Inventors: Madhusudhan R. Gowravaram, Jeffrey Johnson, Ewell R. Cook, Robert C. Wahl, Alan M. Mathiowetz, Bruce E. Tomczuk, Ashis K. Saha
  • Patent number: 5514713
    Abstract: Disclosed are amidinophenol derivatives of the formula (I) and acid-addition salts thereof (in which R.sup.1 and R.sup.2 are alkyl, alkoxy, acyl, halogen, nitro, benzoyl, COOR.sub.4 ; A is bond, alkylene, group of the formula (II); R.sup.3 is group of the formula (III), (IV)) ##STR1## Compounds of the formula (I) have inhibitory activities on phospholipase A.sub.2 and proteases (especially trypsin), and are useful for the prevention and/or the treatment of inflammatory diseases, allergic diseases, disseminated intravascular coagulation, pancreatitis, severity in pancreatitis and multiple organ failure.
    Type: Grant
    Filed: December 2, 1994
    Date of Patent: May 7, 1996
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Hisao Nakai, Koumei Kamiyasu, Masanori Kawamura
  • Patent number: 5510506
    Abstract: A process is disclosed to produce a carboxylic acid derivative of the general formula VIII!: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and L are each as defined in the specification, characterized in that a benzyl halide is reacted with a cyano compound to give a phenylacetonitrile, which is then reacted with an alkyl nitrite in the presence of a base to give an .alpha.-hydroxyiminophenylacetonitrile, which is then reacted with an alkylating agent to give an .alpha.-alkoxyiminophenylacetonitrile, which is then hydrolyzed in the presence of a base, or is hydrated and treated with an acid, followed by hydrolysis in the presence of a base, to give an .alpha.-alkoxyiminophenylacetic acid, which is then reacted with an acid halide forming agent, or is convened into a metal salt, followed by reaction with an alkylating agent, or is reacted with a lower alcohol in the presence of an acid catalyst.
    Type: Grant
    Filed: March 27, 1995
    Date of Patent: April 23, 1996
    Assignees: Shionogi & Co., Ltd., Sumitomo Chem.Co., Ltd.
    Inventors: Akira Takase, Hiroyuki Kai, Moriyasu Masui, Katuhisa Masumoto, Akihiko Nakamura, Yujiro Kiyoshima, Mikio Sasaki
  • Patent number: 5498755
    Abstract: Compounds of the formula ##STR1## wherein the R.sub.1 groups independently are hydrogen, lower alkyl, or two geminal R.sub.1 groups jointly represent an oxo (.dbd.O) or a thio (.dbd.S) group; R.sub.2 is hydrogen or lower alkyl, or halogen; M is or --N.dbd.CR.sub.4 -- or --R.sub.4 C.dbd.N-- where R.sub.4 is hydrogen or lower alkyl; X is C(R.sub.1).sub.2 ; Y is phenyl optionally substituted with an R.sub.3 group which is lower alkyl or halogen; A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl, cycloalkyl, alkenyl, alkynyl; B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.13 O, --COR.sub.7, CR.sub.7 (OR.sub.12).sub.2, or CR.sub.7 OR.sub.13 O, where R.sub.7 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons, R.sub.8 is an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R.sub.8 is phenyl or lower alkylphenyl, R.
    Type: Grant
    Filed: August 23, 1994
    Date of Patent: March 12, 1996
    Inventors: Roshantha A. Chandraratna, Min Teng
  • Patent number: 5489704
    Abstract: The present invention relates to an aldimine/aspartate corresponding to the formula ##STR1## wherein X represents an organic group which has a valency of n and is inert towards isocyanate groups at a temperature of 100.degree. C. or less,R.sub.1 and R.sub.2 may be the same or different and represent optionally substituted hydrocarbon radicals, or R.sub.1 and R.sub.2 together with the .beta.-carbon atom form a cycloaliphatic or heterocyclic ring andR.sub.3 and R.sub.4 may be identical or different and represent organic groups which are inert towards isocyanate groups at a temperature of 100.degree. C. or less,R.sub.5 and R.sub.6 may be identical or different and represent hydrogen or organic groups which are inert towards isocyanate groups at a temperature of 100.degree. C. or less, anda and b represent integers with a value of 1 to 5, provided that the sum of a and b is 2 to 6.
    Type: Grant
    Filed: August 29, 1994
    Date of Patent: February 6, 1996
    Assignees: Bayer Corporation, Bayer Aktiengesellschaft
    Inventors: Edward P. Squiller, Christian Zweiner
  • Patent number: 5488159
    Abstract: A compound of the formula [I]: ##STR1## wherein X is hydrogen, lower alkyl, lower alkoxy or halogen; .about. is any configuration of E-isomer, Z-isomer or a mixture thereof is produced by reacting a compound of the formula [II] ##STR2## wherein X and .about. are as defined above; W is --CN or --COOR; and R is a lower alkyl, with methylamine in the presence of methanol. The compound [I] is useful for an agricultural fungicide. An intermediate used for producing the compound [I] is also disclosed.
    Type: Grant
    Filed: August 25, 1994
    Date of Patent: January 30, 1996
    Assignee: Shionogi & Co., Ltd.
    Inventors: Akira Takase, Hiroyuki Kai, Kuniyoshi Nishida, Shoji Shinomoto, Masahiko Nagai
  • Patent number: 5481021
    Abstract: This invention relates to phenyl amidine derivatives having the following formula ##STR1## or a pharmaceutically acceptable salt which are useful in the inhibition of platelet aggregation. This invention also relates to pharmaceutical compositions of such phenyl amidine derivatives.
    Type: Grant
    Filed: December 22, 1994
    Date of Patent: January 2, 1996
    Assignee: G. D. Searle & Co.
    Inventors: Robert B. Garland, Masateru Miyano, Jeffery A. Zablocki, Lori A. Schretzman
  • Patent number: 5480998
    Abstract: An oxime derivative (I): ##STR1## that D ring and B bonding to D ring are (i)-(iv), wherein R.sup.1 is hydrogen, lower alkyl; R.sup.2 is hydrogen, alkyl, phenyl, cycloalkyl, monocyclic ring containing nitrogen, lower alkyl substituted by benzene ring or cycloalkyl, lower alkyl substituted by monocyclic ring containing nitrogen; R.sup.3 is alkyl, phenyl, cycloalkyl, monocyclic ring containing nitrogen, lower alkyl substituted by benzene ring or cycloalkyl, lower alkyl substituted by monocyclic ring containing nitrogen; e is 3-5, f is 1-3, p is 1-4, q is 1-2, r is 1-3; the position of the bond to D ring in (iii) and (iv) is a or b, and the ring in R.sup.2 and R.sup.3 may be substituted by lower alkyl, alkoxy, halogen, nitro, trihalomethyl; and salts thereof, possess an agonistic activity on PGl2 receptor, and therefore are useful for prevention and/or treatment of thrombosis, arteriosclerosis, ischemic heart diseases, gastric ulcer and hypertension.
    Type: Grant
    Filed: March 17, 1994
    Date of Patent: January 2, 1996
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Nobuyuki Hamanaka, Kanji Takahashi, Hidekado Tokumoto
  • Patent number: 5468775
    Abstract: The present invention concerns enaminones having the formula: ##STR1## wherein R is from the group consisting of COOCH.sub.3 and COOC.sub.2 H.sub.5 ; R.sup.1 is from the group consisting of H and CH.sub.3 ; R.sup.2 is from the group consisting of H when R.sup.1 is CH.sub.3 and CH.sub.3 when R.sup.1 is H; and R.sup.3 is from the group of first radicals consisting of benzyl, phenethyl, disubstituted phenyl and trisubstituted phenyl. The substituted species are second radicals having positive lipophilicity selected from the group consisting of F, Cl, Br, and I.
    Type: Grant
    Filed: March 2, 1993
    Date of Patent: November 21, 1995
    Assignee: Howard University
    Inventors: Kenneth R. Scott, Jesse M. Nicholson, Ivan O. Edafiogho
  • Patent number: 5464809
    Abstract: Fungicidal new 2-methoximinocarboxylic esters of the general formula (I) ##STR1## in which Ar represents one of the radicals ##STR2## and A represents one of the radicals --CH.sub.2 --; ##STR3## where Y represents one of the radicals ##STR4## --O--CH.sub.2 --; --CH.sub.2 --O--; --S--CH.sub.2 --; ##STR5## --SO.sub.2 --CH.sub.2 --; --O--; --CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --,n represents the number 0 or 1,R represents alkyl, halogenoalkyl, alkenyl, halogenoalkenyl, or represents optionally substituted cycloalkyl, or represents optionally substituted aryl or represents optionally substituted heteroaryl, and, moreover, in the event that n is 0, also represents halogen, andX.sup.1, X.sup.2, X.sup.3 and X.sup.4 independently of one another in each case represent hydrogen, halogen, hydroxyl or methoxy, but where, in the event that X.sup.2 represents bromine, X.sup.3 does not simultaneously represent hydroxyl or methoxy.
    Type: Grant
    Filed: September 12, 1994
    Date of Patent: November 7, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfgang Kramer, Dieter Berg, Heinz-Wilhelm Dehne, Stefan Dutzmann
  • Patent number: 5455274
    Abstract: The invention relates to the compounds of the formula ##STR1## wherein the C(=NOH)-NH.sub.2 group may be in tautomeric form, and pharmaceutically acceptable salts thereof, in which:R.sub.1 is amino or amino which is mono- or disubstituted by a substituent selected from an aliphatic hydrocarbon radical, an araliphatic hydrocarbon radical, an aromatic radical, and a cycloaliphatic hydrocarbon radical or is amino which is disubstituted by a divalent aliphatic hydrocarbon radical or a said radical interrupted by oxygen;R.sub.2 is hydrogen, halogen, trifluoromethyl, an aliphatic hydrocarbon radical or hydroxy; or R.sub.2 is hydroxy which is etherified by an aliphatic alcohol, araliphatic alcohol, or aromatic alcohol or which is esterified by an aliphatic or araliphatic carboxylic acid; or R.sub.2 is hydroxy which is etherified by an aliphatic alcohol which is substituted by carboxy, by esterified carboxy or by amidated carboxy;X.sub.1 and X.sub.
    Type: Grant
    Filed: December 9, 1992
    Date of Patent: October 3, 1995
    Assignee: Ciba-Geigy Corporation
    Inventor: Hongsuk Suh
  • Patent number: 5453440
    Abstract: This invention relates to compounds having the following formula ##STR1## or pharmaceutically acceptable salt thereof which are useful in the inhibition of platelet aggregation, to pharmaceutical compositions of such phenylamidines derivatives, and to a method of inhibiting platelet aggregation in mammals by administering such compounds and compositions.
    Type: Grant
    Filed: October 15, 1993
    Date of Patent: September 26, 1995
    Assignee: G. D. Searle & Co.
    Inventors: Philippe R. Bovy, Robert B. Garland, Masateru Miyano, Joseph G. Rico, Thomas E. Rogers, Jeffery A. Zablocki
  • Patent number: 5449809
    Abstract: Acetylene derivatives of the general formula I ##STR1## where U, V and W are hydrogen, halogen, nitro, cyano, alkyl or alkoxy,A is alkylidene, alkoxymethylidene, alkylthiomethylidene or alkoximino,B is OH, alkoxy or alkylamino andR is hydrogen, halogen, cyano, CF.sub.3, alkyl, cycloalkyl, haloalkyl, aryl, alkenyl, alkynyl, heterocyclyl, hetaryl, arylalkyl, arylalkenyl, arylethynyl, hetaryl-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl, aryloxyalkyl, hetaryloxyalkyl, arylamino-alkyl, arylthiomethyl, hetarylthiomethyl, C(O)R.sup.1, C(O)NR.sup.2 R.sup.3, C(S)NR.sup.4 R.sup.5, C(O)SR.sup.6, C(S)OR.sup.7, C(S)SR.sup.8, CH(OH)R.sup.9, CH(OR.sup.10)R.sup.11, SiR.sup.12 R.sup.13 R.sup.14, SnR.sup.15 R.sup.16 R.sup.17, C(OR)R.sup.18 or C(.dbd.N--OR.sup.19)R.sup.20 andR.sup.1 -R.sup.17, R.sup.19 and R.sup.20 are hydrogen, alkyl, aryl, hetaryl, arylalkyl or hetarylalkyl and R.sup.18 is OH, C.sub.1 -C.sub.4 -alkoxy or aryl-C.sub.1 -C.sub.4 -alkoxy, and fungicides containing these compounds.
    Type: Grant
    Filed: July 30, 1993
    Date of Patent: September 12, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Horst Wingert, Beate Hellendahl, Reinhard Kirstgen, Hubert Sauter, Eberhard Ammermann, Gisela Lorenz
  • Patent number: 5432197
    Abstract: Compounds having the formula (I) : ##STR1## and stereoisomers thereof, wherein A is hydrogen, halo, hydroxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.1-4 haloalkoxy, C.sub.1-4 alkylcarbonyl, C.sub.1-4 alkoxycarbonyl, phenoxy, nitro or cyano; R.sup.1 and R.sup.2, which may be the same or different, are hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted heterocyclylalkyl, optionally substituted cycloalkylalkyl, optionally substituted aralkyl, optionally substituted heteroarylalkyl, optionally substituted aryloxyalkyl, optionally substituted heteroaryloxyalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted aryloxy, optionally substituted heteroaryloxy, nitro, halo, cyano, --NR.sup.3 R.sup.4, --CO.sub.2 R.sup.3, --CONR.sup.3 R.sup.4, --COR.sup.3, --S(O).sub.n R.sup.3 wherein n is 0, 1 or 2, (CH.sub.2).sub.
    Type: Grant
    Filed: August 25, 1994
    Date of Patent: July 11, 1995
    Assignee: Zeneca Limited
    Inventors: Paul J. de Fraine, Anne Martin
  • Patent number: 5430172
    Abstract: A process for preparing 4-alkanoylaryl benzyl ethers of the general formula I ##STR1## where R is hydrogen, halogen, cyano; alkyl, alkoxy;X is CH.sub.2, CH--CH.sub.3, CH--CH.sub.2 --CH.sub.3, CH--OCH.sub.3 or N--OCH.sub.3 ;Y is oxygen, sulfur, direct linkage or nitrogen;m is 0, 1, 2 or 3;R.sup.1 is hydrogen; alkyl, alkenyl, alkynyl or alkoxy;R.sup.2 is cyano, halogen, alkyl, alkoxy or haloalkyl;R.sup.3 is alkyl; haloalkyl; cycloalkyl; or an unsubstituted or substituted mono- to trinuclear aromatic system,comprises reacting an aryl benzyl ether of the general formula II ##STR2## where X, Y, R, R.sup.1, R.sup.2 and m have the abovementioned meanings, with a carbonyl halide or with a carboxylic anhydride or with a carboxylic sulfonic anhydride in the presence of an acid and in the presence or absence of a diluent.
    Type: Grant
    Filed: April 15, 1994
    Date of Patent: July 4, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Wassilios Grammenos, Wolfgang Siegel, Klaus Oberdorf, Bernd Mueller, Hubert Sauter, Reinhard Doetzer
  • Patent number: 5414791
    Abstract: Novel acceptor-donor-acceptor compounds for use in forming a thermally-stable electro-optic waveguide are disclosed. Also disclosed is a thermally stable waveguide material containing thermally stable acceptor-donor-acceptor or donor-acceptor-donor guest dipole compounds in dissolved form in a polyimide matrix. The waveguide has selected regions in which the net dipoles of the guest molecules are oriented, for electro-optic switching when an electric field is placed across these regions.
    Type: Grant
    Filed: October 5, 1993
    Date of Patent: May 9, 1995
    Assignee: Lockheed Missiles & Space Company, Inc.
    Inventors: Susan P. Ermer, Doris S. Leung, Steven M. Lovejoy
  • Patent number: 5412149
    Abstract: A new process and new intermediates are described for the preparation of 2-oximinoactic acid derivatives of the formula (I) ##STR1## in which R.sup.1, R.sup.2, n, Z and Ar have the meaning given in the description and which are used as pesticides.
    Type: Grant
    Filed: May 6, 1994
    Date of Patent: May 2, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dietmar Kuhnt, Herbert Gayer, Peter Gerdes
  • Patent number: 5412148
    Abstract: Disclosed are amplifier molecules: various organic compounds having branched structures terminating with amine groups to which pharmacologically active groups can be chemically attached. A number of MRI contrast-enhancing agents were synthesized, each comprising plural active groups, such as stable nitroxides and complexes of trivalent metal cations. Such syntheses were successfully performed using a number of amplifiers having different branched structures, demonstrating the general utility of the pertinent chemistry in the synthesis of amplifiers having any of a wide variety of pharmacologically active groups. Amplifiers were also synthesized having linkers terminating with chemically reactive groups such as isothiocyanates, which render the amplifier bifunctional: attachable to polymers, biomacromolecules, or other biocompatible entity possessing multiple reactive sites such as terminal amines.
    Type: Grant
    Filed: October 6, 1993
    Date of Patent: May 2, 1995
    Assignee: The State of Oregon Acting by and Through the State Board of Higher Education on Behalf of the University of Oregon
    Inventor: John F. W. Keana
  • Patent number: 5410056
    Abstract: The present invention is directed to a novel process for the production of folic acid in high yield utilizing a novel diimine as an intermediate. This diimine is formed by reacting 2-substituted malondialdehyde with p-aminobenzoyl-L-glutamic acid. This diimine may be converted into folic acid by reacting said diimine with triaminopyrimidinone in the presence of sulphite.
    Type: Grant
    Filed: January 6, 1994
    Date of Patent: April 25, 1995
    Assignee: Hoffman-La Roche Inc.
    Inventor: Christof Wehrli
  • Patent number: 5389619
    Abstract: Compounds of the formula I ##STR1## where n, W, X, Y, Z, R.sup.1, R.sup.2, and R.sup.3 are as defined herein exhibit fungicidal, insecticidal, and acaracidal activity.
    Type: Grant
    Filed: March 29, 1993
    Date of Patent: February 14, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Reinhard Doetzer, Hubert Sauter, Horst Wingert, Reinhard Kirstgen, Albrecht Harreus, Gisela Lorenz, Eberhard Ammermann
  • Patent number: 5387607
    Abstract: O-Benzyloxime ethers of the formula I ##STR1## where X is substituted or unsubstituted CH.sub.2, NOalkylY isO, S, NR.sup.5R.sup.1, R.sup.2, R.sup.5 are H, alkylZ.sup.1, Z.sup.2 are H, halogen, methyl, methoxy, cyanoR.sup.3, R.sup.4 are hydrogen, cyano, substituted or unsubstituted alkyl, alkenyl, cycloalkyl, cycloalkenyl, alkynyl, alkoxy, haloalkoxy, alkylthio, benzylthio, alkylcarbonyl, substituted or unsubstituted phenylcarbonyl, substituted or unsubstituted benzylcarbonyl, alkoxycarbonyl, substituted or unsubstituted phenoxycarbonyl, substituted or unsubstituted benzyloxycarbonyl,N(R.sup.6).sub.2, where R.sup.6 is H, alkyl, substituted or unsubstituted phenyl,--CO--N(R.sup.7).sub.2, where R.sup.
    Type: Grant
    Filed: December 13, 1993
    Date of Patent: February 7, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Siegbert Brand, Uwe Kardorff, Reinhard Kirstgen, Bernd Mueller, Klaus Oberdorf, Hubert Sauter, Gisela Lorenz, Eberhard Ammermann, Christoph Kuenast, Albrecht Harreus
  • Patent number: 5380913
    Abstract: A compound of the formula [I]: ##STR1## wherein X is hydrogen, lower alkyl, lower alkoxy or halogen; is any configuration of E-isomer, Z-isomer or a mixture thereof is produced by reacting a compound of the formula [II] ##STR2## wherein X and are as defined above; W is --CN or --COOR; and R is a lower alkyl, with methylamine in the presence of methanol. The compound [I] is useful for an agricultural fungicide. An intermediate used for producing the compound [I] is also disclosed.
    Type: Grant
    Filed: September 14, 1993
    Date of Patent: January 10, 1995
    Assignee: Shionogi & Co., Ltd.
    Inventors: Akira Takase, Hiroyuki Kai, Kuniyoshi Nishida, Shoji Shinomoto, Masahiko Nagai
  • Patent number: 5380914
    Abstract: Fungicidal new 2-methoximinocarboxylic esters of the general formula (I) ##STR1## in which Ar represents one of the radicals ##STR2## A represents one of the radicals ##STR3## where Y represents one of the radicals ##STR4## n represents the number 0 or 1, R represents alkyl, halogenoalkyl, alkenyl, halogenoalkenyl, or represents optionally substituted cycloalkyl, or represents optionally substituted aryl or represents optionally substituted heteroaryl, and, moreover, in the event that n is 0, also represents halogen, andX.sup.1, X.sup.2, X.sup.3 and X.sup.4 independently of one another in each case represent hydrogen, halogen, hydroxyl or methoxy, but where, in the event that X.sup.2 represents bromine, X.sup.3 does not simultaneously represent hydroxyl or methoxy.
    Type: Grant
    Filed: December 7, 1993
    Date of Patent: January 10, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfgang Kramer, Dieter Berg, Heinz-Wilhelm Dehne, Stefan Dutzmann
  • Patent number: 5374769
    Abstract: Novel polycyanate compositions containing one or more mesogenic moieties as lateral substituents are disclosed which provide improved processability relative to polycyanates containing one or more mesogenic moieties in the main chain of the molecule. Molecular level ordering of the resulting thermosets is maintained much similar to that found thermosets of polycyanates which have one or more mesogenic moieties in the main chain.
    Type: Grant
    Filed: December 24, 1992
    Date of Patent: December 20, 1994
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls
  • Patent number: 5371268
    Abstract: Ortho-substituted benzyl esters of cyclopropanecarboxylic acids I ##STR1## where X is N or CH and A is one of the following cyclopropane radicals: ##STR2## where R.sup.1 is CN, C.sub.2 -C.sub.8 -alkyl, CF.sub.3, C.sub.3 -C.sub.8 -alkenyl, (C.sub.1 -C.sub.4 -alkoxycarbonyl, unsubstituted or substituted phenyl-C.sub.1 -C.sub.6 -alkyl or phenyl-C.sub.3 -C.sub.6 -alkenyl, ethoxyphenyl, 2- or 3-bromophenyl, 2- or 4-trifluoromethylphenyl, 2,4- or 2,6-difluorophenyl, 2-fluoro-6-chlorophenyl, 2,4- or 2,6-dimethylphenyl, 2,3,6-trichlorophenyl or trimethylsilyl, R.sup.2 is H or halogen, R.sup.3 is unsubstituted or substituted phenyl, R.sup.4 is CH.sub.3 or halogen and Hal is halogen, with the proviso that X is CH when R.sup.1 is CF.sub.3 or trimethylsilyl, are suitable as fungicides and for controlling pests.
    Type: Grant
    Filed: March 14, 1994
    Date of Patent: December 6, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Schuetz, Hubert Sauter, Norbert Goetz, Jochen Wild, Hans-Josef Wolf, Reinhard Doetzer, Gisela Lorenz, Eberhard Ammermann, Christoph Kuenast, Uwe Kardorff
  • Patent number: 5371084
    Abstract: Compounds having the formula (I): ##STR1## and stereoisomers thereof, wherein A is hydrogen, halo, hydroxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.1-4 haloalkoxy, C.sub.1-4 alkylcarbonyl, C.sub.1-4 alkoxycarbonyl, phenoxy, nitro or cyano; R.sup.1 and R.sup.2, which may be the same or different, are hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted heterocyclylalkyl, optionally substituted cycloalkylalkyl, optionally substituted aralkyl, optionally substituted heteroarylalkyl, optionally substituted aryloxyalkyl, optionally substituted heteroaryloxyalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted aryloxy, optionally substituted heteroaryloxy, nitro, halo, cyano, --NR.sup.3 R.sup.4, --CO.sub.2 R.sup.3, --CONR.sup.3 R.sup.4, --COR.sup.3, --S(O).sub.n R.sup.3 wherein n is 0, 1 or 2, (CH.sub.2).sub.m PO(OR.
    Type: Grant
    Filed: October 28, 1993
    Date of Patent: December 6, 1994
    Assignee: Zeneca Limited
    Inventors: Paul J. de Fraine, Anne Martin
  • Patent number: 5354883
    Abstract: E-Oxime ethers of phenylglyoxylic esters of the formula I ##STR1## X, Y=halogen, alkyl, alkoxy, CF.sub.3, C(.dbd.NOR)R (R=alkyl or alkenyl) are prepared by reacting oximes of the formula II ##STR2## with a methylating agent in an organic diluent, and E-oximes of phenylglyoxylic esters of the formula II are prepared by isomerizing the E/Z-oximes.
    Type: Grant
    Filed: February 5, 1993
    Date of Patent: October 11, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinz Isak, Michael Keil, Bernd Wolf, Horst Wingert
  • Patent number: 5344957
    Abstract: Novel substituted .beta. amino acid derivatives are provided which inhibit platelet aggregation. This invention also pertains to pharmaceutical compositions and methods of using such derivatives.
    Type: Grant
    Filed: October 6, 1992
    Date of Patent: September 6, 1994
    Assignees: G.D. Searle & Co., Monsanto Company
    Inventors: Philippe R. Bovy, Joseph G. Rico, Thomas E. Rogers, Foe S. Tjoeng, Jeffery A. Zablocki
  • Patent number: 5338868
    Abstract: A process is disclosed for the preparation of a compound of the Formula (VI) ##STR1## wherein X is a hydrogen atom, or OH,Y is a hydrogen atom, OH or a methyl group,R.sup.2 is a CH--COOR group, or a group of the formula (XI) ##STR2## and R is a C.sub.1 to C.sub.2 alkyl group, which comprises the step of: reacting a condensed salt of the Formula (IV) ##STR3## wherein Me is Na.sup.+ or K.sup.+, with a reactive derivative of trifluoromethane-sulfonic acid of the Formula (V)F.sub.3 C--SO.sub.2 OH.The compounds of the Formula (VI) are intermediates in the preparation of penicillins and cephalosporins with antibiotic activity.
    Type: Grant
    Filed: May 24, 1991
    Date of Patent: August 16, 1994
    Assignee: Chinoin Gyogyszer- es Vegyeszeti Termekek Gyara Rt.
    Inventors: Karoly Ban, Annamaria Ban, Lajosne Pali, Marta Kruppa, Eva Somfai, Csaba Huszar
  • Patent number: 5334607
    Abstract: Antimycotics containing a compound of the formula ##STR1## where .dbd.Y is .dbd.CH--OCH.sub.3, .dbd.CH--CH.sub.3, .dbd.CH--CH.sub.2 --CH.sub.3, .dbd.CH--SCH.sub.3 or .dbd.N--OCH.sub.3, and X is oxygen, or X may also be NH if Y is .dbd.N--OCH.sub.3,Z is halogen, nitro, cyano, unsubstituted or substituted organic radicals, OR.sup.12, SR.sup.13, SOR.sup.14, SO.sub.2 R.sup.15, --COOR.sup.16, --CONR.sup.17 R.sup.18, --COR.sup.19, --CR.sup.20 .dbd.NR.sup.21, --N.dbd.CR.sup.22 R.sup.23, --CR.sup.24 .dbd.N--OR.sup.25, --CR.sup.25 R.sup.26 --O--N.dbd.CR.sup.27 R.sup.28 andU, V, W can be hydrogen or one of the meanings given for Z, or where two of Z, U, V and W in adjacent positions on the phenyl ring can form an unsubstituted or substituted five- or six-membered, aromatic or aliphatic ring which may contain one to three hetero atoms (N, S, O), and R.sup.12 to R.sup.26 are identical or different and are hydrogen, unsubstituted or substituted organic radicals,are used for controlling mycoses.
    Type: Grant
    Filed: May 28, 1992
    Date of Patent: August 2, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Hubert Sauter, Gisela Lorenz, Gerd Steiner, Bernd Janssen, Timm Anke, Wolfgang Steglich
  • Patent number: 5319122
    Abstract: This invention relates to a novel process for preparing benzylformimidates which are useful in the production of certain carbapenem antibiotics. The process of this invention provides a means of producing a high-yield, high-purity product.
    Type: Grant
    Filed: November 12, 1992
    Date of Patent: June 7, 1994
    Assignee: Merck & Co., Inc.
    Inventor: Joel J. Friedman
  • Patent number: 5312960
    Abstract: Fungicidal new 2-methoximinocarboxylic esters of the general formula (I) ##STR1## in which Ar represents one of the radicals ##STR2## A represents one of the radicals --CH.sub.2 --; ##STR3## where Y represents one of the radicals ##STR4## --SO.sub.2 --CH.sub.2 --; --O--; --CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --,n represents the number 0 or 1,R represents alkyl, halogenoalkyl, alkenyl, halogenoalkenyl, or represents optionally substituted cycloalkyl, or represents optionally substituted aryl or represents optionally substituted heteroaryl, and, moreover, in the event that n is 0, also represents halogen, andX.sup.1, X.sup.2, X.sup.3 and X.sup.4 independently of one another in each case represent hydrogen, halogen, hydroxyl or methoxy, but where, in the event that X.sup.2 represents bromine, X.sup.3 does not simultaneously represent hydroxyl or methoxy.
    Type: Grant
    Filed: June 4, 1991
    Date of Patent: May 17, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfgang Kramer, Dieter Berg, Heinz-Wilhelm Dehne, Stefan Dutzmann
  • Patent number: 5312962
    Abstract: The invention relates to a process for the production of organic compounds containing aldimine or ketimine groups by the reaction of compounds containing .beta.-ketoester groups with bis-aldimines or bis-ketimines with elimination of aldehyde or ketone and to the preferred compounds obtained by this process.
    Type: Grant
    Filed: July 2, 1992
    Date of Patent: May 17, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Walter Schafer, Hanns-Peter Muller
  • Patent number: 5302739
    Abstract: Compounds of the formula ##STR1## as intermediates for the preparation of pyrimidine or triazine herbicides.
    Type: Grant
    Filed: October 29, 1992
    Date of Patent: April 12, 1994
    Assignees: Kumiai Chemical Industry Co., Ihara Chemical Industry Co., Ltd.
    Inventors: Masatoshi Tamaru, Norihiro Kawamura, Masahiro Sato, Fumiaki Takabe, Shigehiko Tachikawa, Ryo Yoshida