Isothiocyanate Esters (i.e., Compounds Containing The Isothiocyanate Group, -n=c=s, Bonded Directly To Carbon, Which Carbon May Be Single Bonded To Any Atom But May Be Multiple Bonded Only To Carbon) Patents (Class 558/17)
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Publication number: 20040142378Abstract: Disclosed is a probe for mass spectrometry of liquid samples, which may effectively ionize the sample without adding a protic solvent to the mobile phase in the ionization method in mass spectrometry of liquid samples.Type: ApplicationFiled: September 5, 2003Publication date: July 22, 2004Inventors: Koji Suzuki, Yoshio Suzuki
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Publication number: 20040127697Abstract: Novel arylisothiocyanate compounds are described that are useful for activating alcohol-containing macromolecules, for example polyethyleneglycols and cellulose, for covalent linkage to amino-groups of biomolecules, for example polypeptides such as antibodies, enzymes, and proteins.Type: ApplicationFiled: December 19, 2003Publication date: July 1, 2004Inventor: Paul K. Smith
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Publication number: 20040106798Abstract: The invention relates to fluorinated fluorene derivatives of negative DC anisotropy, of the formula IType: ApplicationFiled: September 29, 2003Publication date: June 3, 2004Inventors: Matthias Bremer, Detlef Pauluth, Melanie Klasen-Memmer
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Patent number: 6737524Abstract: Novel arylisothiocyanate compounds are described that are useful for activating alcohol-containing macromomolecules, for example polyethyleneglycols and cellulose, for covalent linkage to amino-groups of biomolecules, for example polypeptides such as antibodies, enzymes, and proteins.Type: GrantFiled: March 25, 2002Date of Patent: May 18, 2004Inventor: Paul K. Smith
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Publication number: 20040087810Abstract: In one embodiment, this invention provides a class of androgen receptor targeting agents (ARTA). The agents define a new subclass of compounds, which are selective androgen receptor modulators (SARM). The SARM compounds have unexpected antiandrogenic activity of a nonsteroidal ligand for the androgen receptor. In one embodiment, the SARM compounds bind irreversibly to the androgen receptor. In another embodiment, the SARM compounds are androgen receptor antagonists which bind irreversibly to the androgen receptor. In another embodiment, the SARM compounds are alkylating agents.Type: ApplicationFiled: February 24, 2003Publication date: May 6, 2004Inventors: James T. Dalton, Duane D. Miller, Mitchell S. Steiner, Karen A. Veverka, Leonid I. Kirkovsky, Arnab Mukherjee, Dong Jin Hwang
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Publication number: 20040086460Abstract: New types of hydroxamic acid-based bifunctional chelators are provided. These chelators are designed to chelate metal ions that can be detected either by their paramagnetic or radioactive properties. Conjugation with peptides or protein can be achieved by the presence of a linker moiety in the molecular structure of these chelators.Type: ApplicationFiled: August 4, 2003Publication date: May 6, 2004Inventor: Jean-Marc DuFour
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Patent number: 6723866Abstract: The invention relates to liquid-crystalline compounds of the formula I in which R1, A1, A2, Z1, Z2, a, b, L1, L2 and L3 are as defined in claim 1, and to liquid-crystalline media comprising at least compound of the formula I and to electro-optical displays containing a liquid-crystalline medium of this type.Type: GrantFiled: July 25, 2002Date of Patent: April 20, 2004Assignee: Merck Patent Gesellschaft mit Beschränkter HaftungInventors: Peer Kirsch, Michael Heckmeier, Joachim Krause, Marc Lenges, Gerald Unger
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Patent number: 6653321Abstract: Methods for treating conditions associated with hyperglycemia, especially Type II diabetes, with novel naphthylsulfonic acids and related compounds. These compounds, as single stereoisomers or mixtures of stereoisomers, or their pharmaceutically acceptable salts, are useful in methods of stimulating the kinase activity of the insulin receptor, enhancing the activation of the insulin receptor by insulin, and stimulating the uptake of glucose into cells. A variety of antidiabetic compounds and pharmaceutical compositions comprising the antidiabetic compounds are also disclosed.Type: GrantFiled: July 28, 2000Date of Patent: November 25, 2003Assignee: Telik, Inc.Inventors: Wayne R. Spevak, Songyuan Shi, Prasad V. V. S. V. Manchem, Michael R. Kozlowski, Steven R. Schow, Robert T. Lum, Louise Robinson, Jeong Weon Park
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Publication number: 20030216554Abstract: The invention relates to liquid-crystalline compounds of the formula I 1Type: ApplicationFiled: July 25, 2002Publication date: November 20, 2003Applicant: Merck Patent GmbHInventors: Peer Kirsch, Michael Heckmeier, Joachim Krause, Marc Lenges, Gerald Unger
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Patent number: 6635761Abstract: This invention relates to the use as catalyst for the cyclotrimerization reaction of isocyanates of a hydrogencarbonate of a cation which either as it is or in the form complexed with a complexing agent has an average molecular or ionic radius of more than 1 Å, preferably greater than 1.5 Å, and which is at least partially soluble in the reaction medium. The invention also relates to a method of preparing (poly)isocyanurate polyisocyanates by catalytic cyclotrimerization of isocyanates, in which a catalytic system is used which comprises a cyclotrimerization catalyst based on a quaternary ammonium salt as catalyst and imidazole as cocatalyst.Type: GrantFiled: June 15, 2000Date of Patent: October 21, 2003Assignee: Rhodia ChimieInventors: Denis Revelant, Jean-Marie Bernard
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Publication number: 20030187233Abstract: Perfluoroisopropylbenzene derivatives of the general formula (I) or salts thereof, useful as intermediates or raw materials in the synthesis of various industrial materials including agricultural chemicals, drugs and surfactants, wherein X1 is H, halogeno, formyl, optionally halogenated C1-6 alkyl, —C(═O)—R1 (wherein R1 is H, halogeno, hydroxyl, C1-6 alkyl, or NR2R3, with R2 and R3 being each H, C1-6 alkyl, or the like), or the like; X3 is H, halogeno, hydroxyl, cyano, isocyanato, hydrazino, diazo, —C(═O)—R1, —SO2—R4 (wherein R4 is halogeno, hydroxyl, C1-6 alkyl, or NR5R6, with R5 and R6 being each H or C1-6 alkyl), or the like; and X4 is H, halogeno, C1-6 alkyl, or C1-6 alkoxy, with publicly known compounds being excepted.Type: ApplicationFiled: September 11, 2002Publication date: October 2, 2003Inventors: Masanobu Onishi, Kenichi Ikeda, Takashi Shimaoka, Masanori Yoshida
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Patent number: 6623721Abstract: New types of hydroxamic acid-based bifunctional chelators are provided. These chelators are designed to chelate metal ions that can be detected either by their paramagnetic or radioactive properties. Conjugation with peptides or protein can be achieved by the presence of a linker moiety in the molecular structure of these chelators.Type: GrantFiled: December 18, 2000Date of Patent: September 23, 2003Assignee: Draximage, Inc.Inventors: Richard J. Flanagan, Jean-Marc Dufour
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Patent number: 6569505Abstract: The instant invention relates to liquid crystal media comprising a strongly dielectrically positive component A, preferably comprising isothiocyanate compounds, most preferably compounds of formula I, as given in the text, and a further dielectrically positive component B, preferably comprising terminally polar substituted bi- or terphenyl compounds, most preferably comprising compounds of formula II, as given in the text, further to novel isothiocyanato compounds as well as to liquid crystal displays comprising these media, in particular to PDLC display and most particular to holographic PDLC displays. The instant invention further relates to compounds of formula I wherein the parameters are as as specified in the text.Type: GrantFiled: February 2, 2001Date of Patent: May 27, 2003Assignee: Merck Patent Gesellschaft mit Beschränkter HaftungInventors: Eike Poetsch, Atsutaka Manabe, Volker Reiffenrath, Marcus Reuter, Volker Meyer, Joachim Krause, Detlef Pauluth
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Patent number: 6566403Abstract: This invention relates to new compositions comprising predominantly one enantiomer of an N-acetonylbenzamide fungicide, methods of preparing N-acetonylbenzamides, and their use as fungicides.Type: GrantFiled: June 16, 1997Date of Patent: May 20, 2003Assignee: Dow AgroSciences LLCInventors: Enrique Luis Michelotti, David Hamilton Young, Thomas Anthony McLaughlin
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Patent number: 6420556Abstract: The subject invention involves novel acyl isothiocyanate resins of formula (I) and processes for making them: (a) starting with a phenyl carboxy resin, treating the resin with any reagent that converts the carboxy to an acyl halide, followed by treatment with tetranikylammonium thiocyanate or an alkali metal salt thereof, to provide the acyl isothiocyanate resin. The subject invention also involves processes for making guanidine compounds and related cyclized compounds using an acyl isothiocyanate resin, comprising the following steps: (b) reacting the acyl isothiocyanate resin with a primary amine; (c) reacting the product from Step (b) with a sulfur activating agent and ammonia or a primary or secondary amine; (d) treating the product from Step (c) with a strong base or medium strength acid to cleave product from the resin, providing the guanidine compound or/and the related cyclized compound.Type: GrantFiled: June 12, 2001Date of Patent: July 16, 2002Assignee: The Procter & Gamble CompanyInventor: Lawrence Joseph Wilson
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Publication number: 20020076377Abstract: New types of hydroxamic acid-based bifunctional chelators are provided. These chelators are designed to chelate metal ions that can be detected either by their paramagnetic or radioactive properties. Conjugation with peptides or protein can be achieved by the presence of a linker moiety in the molecular structure of these chelators.Type: ApplicationFiled: December 18, 2000Publication date: June 20, 2002Inventors: Richard J. Flanagan, Jean-Marc Dufour
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Publication number: 20020052408Abstract: Novel sulfate ester agents and the use of those agents for treating gastroesophageal reflux disease (GERD) are described, exemplary agents being of the formula: 1Type: ApplicationFiled: July 5, 2001Publication date: May 2, 2002Inventors: Richard A. Hudson, Liyanaaratchinge M.V. Tillekeratne, Nelia A. Tobey, Roy C. Orlando
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Publication number: 20010012839Abstract: The present invention relates to an antiandrogen compound and a method of treating prostate cancer in a patient utilizing the compound. The present invention also relates to a pharmaceutical composition which includes the compound.Type: ApplicationFiled: February 22, 2000Publication date: August 9, 2001Inventors: Duane D Miller, Leonid I Kirkovsky, James T Dalton, Arnab Mukherjee
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Patent number: 5874466Abstract: Novel routes for the preparation of acetonylbenzamides are provided by the reaction of an amine and acyl chloride. Novel routes to various intermediates used in the manufacture of acetonylbenzamides are also disclosed.Type: GrantFiled: June 10, 1997Date of Patent: February 23, 1999Assignee: Rohm and Haas CompanyInventors: Enrique Luis Michelotti, Heather Lynnette Rayle, Randall Wayne Stephens, William Joseph Zabrodski
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Patent number: 5808003Abstract: A compound according to the formula: ##STR1## and conjugates thereof.Type: GrantFiled: September 18, 1996Date of Patent: September 15, 1998Assignee: PerImmune Holdings, Inc.Inventors: Ramaswamy Subramanian, James Colony
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Patent number: 5800802Abstract: A method for removing unbound labeling reagent from a composition comprising bound and unbound labeling reagents in which a chelator-matrix conjugate capable of binding unbound labeling reagent is contacted with a biomolecule labeling reaction mixture, by which the unbound labeling reagent is scavenged by the chelator-matrix conjugate, and then the labeled biomolecule essentially free of unbound labeling reagent is removed. Also included is a novel chelator IDAC-2, which may be used for labeling biomolecules and for scavenging in the chelator-matrix conjugate.Type: GrantFiled: May 17, 1995Date of Patent: September 1, 1998Inventors: Ramaswamy Subramanian, James Colony
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Patent number: 5726338Abstract: A process for producing 2-halogenoallyl isothiocyanate ?I! represented by the formula: ##STR1## wherein X.sup.1 is a halogen atom, is disclosed. The process comprises reacting a compound represented by the formula: ##STR2## wherein X.sup.1 is a halogen atom and X.sup.2 is a leaving group, with a thiocyanate represented by the formula;M(SCN)nwherein M is a metal or an ammonium group and n is a valence number of M, in the presence of water under heating. According to the process for producing of the present invention, 2-halogenoallyl isothiocyanata ?I!, which has an insecticidal effect as such and is useful as an intermediate for a medicine, an agricultural chemical and the like, can be produced on an industrially large scale in a good yield.Type: GrantFiled: September 12, 1996Date of Patent: March 10, 1998Assignee: Takeda Chemical Industries, Ltd.Inventors: Hideki Uneme, Yasuo Kamiya
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Patent number: 5668257Abstract: The present invention relates to a novel class of phenylboronic acid complexing reagents useful for the preparation of bioconjugates, and the method of making and using such reagents. In the present invention, in the place of prior art Avidin-Biotin and Digoxigenin-anti-Digoxigenin systems, phenylboronic acid complexing reagents are utilized in conjunction with phenylboronic acid reagents (many of which are known in the prior art) to facilitate chemical conjugation without the use of intermediary biological macromolecules. Reagents suitable for the modification of a bioactive species for the purpose of incorporating a phenylboronic acid complexing moiety for subsequent conjugation to a different bioactive species having pendant phenylboronic acid moieties are of General Formula I or General Formula II. ##STR1## wherein group X is selected from either H, OH, NH.sub.2, NHCH.sub.3, NHOH and NHOCH.sub.Type: GrantFiled: June 7, 1995Date of Patent: September 16, 1997Assignee: Prolinx, Inc.Inventor: Mark L. Stolowitz
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Patent number: 5629346Abstract: Certain N-acetonylbenzamides exhibit low toxicity to plants are particularly useful for control of fungi, especially Phycomycetes.Type: GrantFiled: June 6, 1995Date of Patent: May 13, 1997Assignee: Rohm and Haas CompanyInventors: H. Edwin Carley, Ashok K. Sharma, Colin Swithenbank
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Patent number: 5594151Abstract: The present invention relates to a novel class of phenylboronic acid complexing reagents useful for the preparation of bioconjugates, and the method of making and using such reagents. In the present invention, in the place of prior art Avidin-Biotin and Digoxigenin-anti-Digoxigenin systems, phenylboronic acid complexing reagents are utilized in conjunction with phenylboronic acid reagents (many of which are known in the prior art) to facilitate chemical conjugation without the use of intermediary biological macromolecules. Reagents suitable for the modification of a bioactive species for the purpose of incorporating a phenylboronic acid complexing moiety for subsequent conjugation to a different bioactive species having pendant phenylboronic acid moleties are of General Formula I or General Formula II. ##STR1## wherein group X is selected from either H, OH, NH.sub.2, NHCH.sub.3, NHOH and NHOCH.sub.Type: GrantFiled: January 28, 1994Date of Patent: January 14, 1997Assignee: Prolinx, Inc.Inventor: Mark L. Stolowitz
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Patent number: 5539138Abstract: The ligands HBED-SCN, HBPD-SCN, and HTDD-SCN are provided which have enhanced ease of reaction with peptides or proteins and which are suitable for chelating with radioisoptopes, especially Indium-.sup.III and Gallium-.sup.67.Type: GrantFiled: July 28, 1994Date of Patent: July 23, 1996Assignee: Merck Frosst Canada, Inc.Inventors: Richard J. Flanagan, Keith T. Hogan, Jean-Marc Dufour, F. Peter Charleson
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Patent number: 5488126Abstract: A new series of bifunctional chelating agents useful for attaching metal ions to proteins, polypeptides and other polymers and methods for their preparation are described. These reagents are unique in their ability to bind a variety of metal ions and to yield a high metal ion concentration per protein molecule. Using these methods polymeric analogs of these bifunctional chelating agents called Starburst ligands can also be obtained. Protein metal chelates thus obtained will have useful radiophysical, chemical, fluorescent, photochemical and magnetic properties suitable for biomedical applications.Type: GrantFiled: February 16, 1994Date of Patent: January 30, 1996Assignee: Akzo Nobel N.V.Inventors: Ramaswamy Subramanian, James L. Colony
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Patent number: 5434287Abstract: The subject matter of the present invention relates to bifunctional cyclohexyl DPTA ligands and methods for utilizing these compounds.Type: GrantFiled: November 4, 1993Date of Patent: July 18, 1995Assignee: The United States of America as represented by the Department of Health and Human ServicesInventors: Otto A. Gansow, Martin W. Brechbiel
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Patent number: 5411986Abstract: Sulforaphane has been isolated and identified as a major and very potent phase II enzyme inducer in broccoli (Brassica oleracea italica). Sulforaphane is a monofunctional inducer, inducing phase II enzymes selectively without the induction of aryl hydrocarbon receptor-dependent cytochromes P-450 (phase I enzymes). Analogues differing in the oxidation state of sulfur and the number of methylene groups were synthesized, and their inducer potencies were measured. Sulforaphane is the most potent of these analogues. Other analogues having different substituent groups in place of the methylsulfinyl group of sulforaphane were also synthesized and assessed. Of these, the most potent are 6-isothiocyanato-2-hexanone and exo-2-acetyl-6-isothiocyanatonorbornane.Type: GrantFiled: March 12, 1993Date of Patent: May 2, 1995Assignee: The Johns Hopkins UniversityInventors: Cheon-Gyu Cho, Gary H. Posner, Paul Talalay, Yuesheng Zhang
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Patent number: 5354777Abstract: New cyanoalkene derivatives of the formula (I) ##STR1## are described, in which R and R.sup.1 have the meaning given in the description, and a process for their preparation.The new cyanoalkene derivatives are used for combating microorganisms for the protection of industrial materials.Type: GrantFiled: February 23, 1993Date of Patent: October 11, 1994Assignee: Bayer AktiengesellschaftInventors: Peter Wachtler, Wilfried Paulus, Georg-Wilhelm Ludwig
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Patent number: 5349062Abstract: Compounds of formula I ##STR1## wherein X.sub.1 and X.sub.2 are each independently of the other O, S or Se, and R.sub.1 and R.sub.2 are each independently of the other a monovalent radical of an aliphatic or aromatic hydrocarbon of 1 to 20 carbon atoms which is unsubstituted or substituted by NH.sub.2, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, phenyl or C.sub.3 -C.sub.8 cycloalkyl. The compounds of formula I are able to form electrically conductive charge transfer complexes.Type: GrantFiled: June 28, 1993Date of Patent: September 20, 1994Assignee: Ciba-Geigy CorporationInventor: John Zambounis
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Patent number: 5310916Abstract: Trifunctional agents useful as inhibitors of A.sub.1 -Adenosine receptors may be formulated into pharmaceutical compositions. These agents are represented by formula (I): ##STR1## wherein X is CH or N, R is an isothiocyanate group, an amino group or --NHCO.sub.2 C(CH.sub.3).sub.3 and R.sup.1 is hydrogen, carboxyl, lower alkoxycarbonyl, aminocarbonyl, ##STR2## lower alkyl, optionally substituted with: --OH, --COOH, lower ester of COOH, carboxamide, NHCOCH.sub.3, NHCOCH.sub.2 Br, halo, dimethylamino, triethylammonium, NHCONH.sub.2, SO.sub.2 NH.sub.2, --SO.sub.3 H, or a reporter group, particularly a spectroscopic reporter group such as a fluorescent dye, photoaffinity probe, or spin label probe, coupled through an amide, sulfonamide, amine or thiourea linkage, biotinylamino- (optionally containing an .epsilon.-aminocaproyl spacer chain or similar spacer chain) or; R.sup.1 is CONH--R.sup.2 or NHCSNH--R.sup.2, wherein R.sup.Type: GrantFiled: August 24, 1990Date of Patent: May 10, 1994Assignee: The United States of America as represented by the Secretary of the Department of Health and Human ServicesInventors: Kenneth A. Jacobson, Gary L. Stiles, Daniel L. Boring
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Patent number: 5308869Abstract: N,N'-disubstituted-amidines, e.g., of the formula ##STR1## wherein R, R' and R" are substituted or unsubstituted hydrocarbon and/or heterocyclic groups.Methods are provided for the treatment or prophylaxis of anxiety in an animal, for treating psychosis, and for treating hypertension by administering an effective amount of an N,N'-disubstituted amidine which, preferably, has a high affinity for the sigma receptor.Type: GrantFiled: March 30, 1992Date of Patent: May 3, 1994Assignee: State of Oregon, acting by and through the Oregon State Board of Higher EducationInventors: John F. W. Keana, Eckard Weber
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Patent number: 5304572Abstract: Novel N-acetonylbenzamides and their use in controlling phytopathogenic fungi.Type: GrantFiled: December 1, 1992Date of Patent: April 19, 1994Assignee: Rohm and Haas CompanyInventors: Enrique L. Michelotti, David H. Young
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Patent number: 5292938Abstract: Cyclo agents useful in forming antibody-metal conjugates useful for diagnostic and therapeutic purposes. New compounds and processes of forming these compounds are disclosed including 4-haloacetamido-trans-1,2-diaminocyclohexyl polyaminocarboxylate and 4-isothiocyanato-trans-1,2-diamino cyclohexane-N,N,N',N'-tetra acetic acid.Type: GrantFiled: April 13, 1992Date of Patent: March 8, 1994Assignee: Associated Universities, Inc.Inventors: Ronnie C. Mease, Leonard F. Mausner, Suresh C. Srivastava
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Patent number: 5254584Abstract: Certain N-acetonylbenzamides exhibit low phytotoxicity and are useful for control of a wide range of fungi, including phytopathogenic fungi of the classes Oomycetes, Ascomycetes, Deuteromycetes and Basidiomycetes.Type: GrantFiled: December 18, 1992Date of Patent: October 19, 1993Assignee: Rohm and Haas CompanyInventors: Enrique L. Michelotti, Robert R. Raney, David H. Young
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Patent number: 5231209Abstract: A method of inhibiting lung tumor multiplicity and/or incidence by treating mammals with relatively long chain arylalkyl isothiocyanates, especially effective with respect to tumors induced by exposure to tobacco-specific nitrosamine. Among the isothiocyanates are 4-phenylbutyl isothiocyanate, phenylpentyl isothiocyanate and phenylhexyl isothiocyanate, which are synthesized by adding hydrochloride of phenylbutylamine, phenylpentylamine, or phenylhexylamine in water to thiophosgene in an inert organic solvent. For comparison testing, oxo-pyridyl butyl isothiocyanate is synthesized by dissolving myosmine in HCl to obtain a hydrochloride salt, suspending the salt in dry chloroform, adding thiophosgene, and adding chloroform containing triethylamine.Type: GrantFiled: December 13, 1991Date of Patent: July 27, 1993Assignee: American Health FoundationInventors: Fung-Lung Chung, Stephen S. Hecht, Karin Eklind, Mark A. Morse
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Patent number: 5227474Abstract: The present invention provides bifunctional chelating agents comprising a unique substrate reactive moiety incorporated into a carboxymethyl arm of a polyaminopolycarboxylate chelating framework capable of forming stable complexes with metal ions.Type: GrantFiled: May 28, 1991Date of Patent: July 13, 1993Assignee: Abbott LaboratoriesInventors: David K. Johnson, Steven J. Kline
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Patent number: 5220000Abstract: Novel bifunctional bis-quinolinols are provided as well as their chelates and processes for their production. The quinolinols can be attached to organic substrates before or after chelation and are useful for diagnostic and therapeutic purposes.Type: GrantFiled: January 23, 1992Date of Patent: June 15, 1993Inventor: Spyros Theodoropulos
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Patent number: 5188759Abstract: The invention relates to a liquid crystalline medium having at least two components, where at least one component is a haloacetylene derivatives of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --(A.sup.2 --Z.sup.2).sub.m --A.sup.3 --C.tbd.C--X IwhereinR.sup.1 is an alkyl or alkenyl radical having up to 15 carbon atoms which is unsubstituted or monosubstituted by CN, halogen or CF.sub.3, or such a radical wherein one or more CH.sub.2 groups is replaced, in each case independently of one another, by --S--, --O--, ##STR1## --CO--, --CO--O--, --O--CO-- or --O--CO--O-- in such a manner that sulfur and/or oxygen atoms are not linked directly to one another,A.sup.1, A.sup.2 and A.sup.3, in each case independently of one another, are(a) a trans-1,4-cyclohexylene radical or --S-- one or more non-adjacent CH.sub.Type: GrantFiled: February 1, 1991Date of Patent: February 23, 1993Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Ekkehard Bartmann, Reinhard Hittich, Herbert Plach, Ulrich Finkenzeller
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Patent number: 5180418Abstract: Cycloalkanecarboxylic acid derivatives of formula I ##STR1## wherein W is ##STR2## and A is CO--R.sub.3 or CN; R.sub.1 is hydrogen or fluorine; R.sub.2 is halogen or cyano; R.sub.3 is chlorine, X--R.sub.5, amino, C.sub.1 -C.sub.4 alkylamino, d-C.sub.1 -C.sub.4 alkylamino, C.sub.2 -C.sub.4 haloalkylamino, di-C.sub.2 -C.sub.4 haloalkylamino, C.sub.1 -C.sub.4 hydroxyalkylamino, di-C.sub.1 -C.sub.4 hydroxyalkylamino, C.sub.3 -C.sub.4 alkenylamino, diallylamino, --N-pyrrolidino, --N-piperidino, --N-morpholino, --N-thiomorpholino, --N-piperidazino, the group --O--N.dbd.C--(R.sub.9)R.sub.10 or the group --N--R.sub.6 (OR.sub.6); each of R.sub.4 and R.sub.14, independently of the other, is hydrogen, fluorine, chlorine, bromine, C.sub.1 -C.sub.4 alkyl or trifluoromethyl; R.sub.5 is hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.10 alkylthio-C.sub.1 -C.sub.4 alkyl, di-C.sub.1 -C.sub.4 alkylamino-C.sub.1 -C.sub.4 alkyl, cyano-C.sub.1 -C.sub.Type: GrantFiled: July 19, 1991Date of Patent: January 19, 1993Assignee: Ciba-Geigy CorporationInventors: Georg Pissiotas, Hans Moser, Hans-Georg Brunner, Eginhard Steiner
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Patent number: 5175257Abstract: Chelating compounds of specified N.sub.2 S.sub.2 N.sub.3 S derived structure are useful for radiolabeling targeting molecules such as antibodies. Cleavable ester orthioester linkers connect the radionuclide metal chelates to the antibodies. The radiolabeled antibodies have improved biodistribution properties, including reduced localization within the intestines and kidneys.Type: GrantFiled: January 14, 1991Date of Patent: December 29, 1992Assignee: NeoRx CorporationInventors: Sudhakar Kasina, Ananthachari Srinivasan, John M. Reno, Linda M. Gustavson, Jeffrey N. Fitzner, David S. Jones
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Patent number: 5141949Abstract: Anxiolytic and antipsychotic treatment is provided to patients by administering therapeutically effective amounts of N-[2-(diethylamino)-ethyl]-2-methoxy-4-[(1-H-4,5-dihydro-2-imidazolyl)-ami no]-5-chlorobenzamide, or a pharmaceutically acceptable salt thereof.Type: GrantFiled: October 31, 1991Date of Patent: August 25, 1992Assignee: Laboratoires Delagrange (Synthelabo)Inventors: Jacques Acher, Jean-Claude Monier, Jean-Paul Schmitt, Brenda Costall, Robert Naylor, Renee Gardaix-Luthereau
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Patent number: 5135562Abstract: Compounds of formula I ##STR1## wherein R.sub.1 is halogen;X is oxygen; or sulfur;Y is oxygen; or sulfur;A is a straight-chain or branched C.sub.1 -C.sub.4 alkylene chain;Q is hydroxy; halogen; cyano; unsubstituted or cyano- or halo-substituted C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.4 alkynyl; --CR.sub.2 .dbd.CH--COOR.sub.3 ; --CH[N(R.sub.2).sub.2 ]COOR.sub.2 ; --NR.sub.4 (R.sub.5); --CO--NR.sub.6 R.sub.7 ; --COON.dbd.CR.sub.8 (R.sub.8); --C(R.sub.2)(OR.sub.9).sub.2 ; --Si(R.sub.10).sub.3 ; --COOCH.sub.2 Si(CH.sub.3).sub.2 --C.sub.1 -C.sub.6 alkyl; ##STR2## --CON(R.sub.12)SO.sub.2 --C.sub.1 -C.sub.6 alkyl; --CON(R.sub.12)SO.sub.2 --C.sub.1 -C.sub.4 haloalkyl; C.sub.1 -C.sub.6 alkylcarbonyl; C.sub.2 -C.sub.6 alkoxyalkylcarbonyl; benzoyl; benzylcarbonyl; --COOR.sub.16 ; --CO--N(R.sub.2)CH.sub.2 --CH.sub.2 --CH(O--C.sub.1 -C.sub.6 alkyl).sub.2 ; --COO(CH.sub.2).sub.j N(R.sub.2).sub.2 ; --S(O).sub.k --R.sub.14 ; --S(O).sub.k --A'--COOR.sub.Type: GrantFiled: March 19, 1991Date of Patent: August 4, 1992Assignee: Ciba-Geigy CorporationInventors: Georg Pissiotas, Hans Moser, Hans-Georg Brunner
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Patent number: 5132313Abstract: The present invention relates to novel NMDA receptor antagonists and methods for their use. The present invention also provided pharmaceutical compositions comprising such NMDA receptor antagonists.Type: GrantFiled: October 26, 1989Date of Patent: July 21, 1992Assignee: University of PittsburghInventors: Alan P. Kozikowski, Yuan-Ping Pang
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Patent number: 5124471Abstract: The subject matter of the present invention relates to bifunctional cyclohexyl DPTA ligands and methods for utilizing these compounds.Type: GrantFiled: March 26, 1990Date of Patent: June 23, 1992Assignee: The United States of America as represented by the Secretary of the Department of Health and Human ServicesInventors: Otto A. Gansow, Martin W. Brechbiel
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Patent number: 5117057Abstract: This invention relates to insecticidal compositions containing N'-substituted-N,N'-disubstitutedhydrazines, methods of using such compositions and N'-substituted-N, N'-disubstitutedhydrazines. Specifically, the invention relates to insect growth regulating compositions, and methods of using such compositions, which include compounds having a nucleus of the formula ##STR1## where A', B', D and J are independently any atom or group of atoms; where E is a tertiary carbon containing organic radical, a haloalkyl having a total of at least four carbon and halogen atoms but not more than six halogen atoms, or a non-tertiary carbon containing non-haloalkyl organic or organometallic radical having at least five atoms other than hydrogen, oxygen and halogen, and is attached to the nitrogen shown in the formula by a carbon-to-nitrogen single bond; where one G.sub.1 is C, N, O and S, and both G.sub.2 's and the other G.sub.1 are carbon; or one G.sub.2 is S or P, and both G.sub.1 's and the other G.sub.Type: GrantFiled: June 14, 1991Date of Patent: May 26, 1992Assignee: Rohm and Haas CompanyInventors: Adam C. Hsu, Harold E. Aller, Raymond A. Murphy, Dat P. Le, Donald W. Hamp, Barry Weinstein
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Patent number: 5101041Abstract: A group of functionalized triamine chelants and their derivatives that form complexes with radioactive metal ions are disclosed. The complexes can be covalently attached to a protein or an antibody or antibody fragment and used for therapeutic and/or diagnostic purposes.Type: GrantFiled: April 26, 1989Date of Patent: March 31, 1992Assignee: The Curators of the University of MissouriInventors: David E. Troutner, Christy S. John, Maroor R. A. Pillai
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Patent number: 5099069Abstract: New polysubstituted diethylenetriaminepentaacetic acid chelates and protein conjugates of the same are described together with the methods of preparing such compounds. A method of delivering radiolabelled compound of the present invention to a target site while minimizing the distribution of the compound to non-targeted organs or tissues is also disclosed.Type: GrantFiled: December 16, 1988Date of Patent: March 24, 1992Inventors: Otto A. Gansow, Martin W. Brechbiel
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Patent number: RE36784Abstract: Sulforaphane has been isolated and identified as a major and very potent phase II enzyme inducer in broccoli (Brassica oleracea italica). Sulforaphane is a monofunctional inducer, inducing phase II enzymes selectively without the induction of aryl hydrocarbon receptor-dependent cytochromes P-450 (phase I enzymes). Analogues differing in the oxidation state of sulfur and the number of methylene groups were synthesized, and their inducer potencies were measured. Sulforaphane is the most potent of these analogues. Other analogues having different substituent groups in place of the methylsulfinyl group of sulforaphane were also synthesized and assessed. Of these, the most potent are 6-isothiocyanato-2-hexanone and exo-2-acetyl-6-isothiocyanatonorbornane.Type: GrantFiled: May 2, 1997Date of Patent: July 18, 2000Assignee: The Johns Hopkins UniversityInventors: Cheon-Gyu Cho, Gary H. Posner, Paul Talalay, Yuesheng Zhang