University of California

Technicon Instruments Corporation

The Upjohn Co.

Miles Inc.

Donald J Cram

Koon-Wah Leong

Bronislaw P Czech

Eddy Chapoteau

Anand Kumar

Carl R Gebauer

Roger C Helgeson

Martin Gall

Michael F Lipton

The present invention resides in the discovery of a new class of compounds defined herein as 'chromogenic hemispherands' useful for the measurement of ions, in particular, ions in aqueous solution, which have the structure ##STR1## wherein: R, same or different, is hydrogen, lower alkyl, lower alkylidene, lower alkenyl, allyl or aryl;

Chromogenic hemispherands and their preparation

The present invention resides in the discovery of a new class of compounds defined herein as 'chromogenic cryptahemispherands' useful for the measurement of ions, in particular, ions in aqueous solution, which have the structure ##STR1## wherein: R, same or different, is hydrogen, lower alkyl, lower alkylidene, lower alkenyl, allyl or aryl;

Chromogenic cryptahemispherands and their preparation

The present invention resides in the discovery of a new class of compounds defined herein as 'chromogenic hemispherands' useful for the measurement of ions, in particular, ions in aqueous solution, methods of using the chromogenic hemispherands and test devices containing the chromogenic hemispherands. The chromogenic hemispherands of the invention have the structure ##STR1## wherein: R, same or different, is hydrogen, lower alkyl, lower alkylidene, lower alkenyl, allyl or aryl;

Method of detecting electrolytes in an aqueous test sample using

The present invention resides in the discovery of a class of compounds defined herein as 'chromogenic cryptahemispherands' useful for the measurement of ions, in particular, ions in aqueous solution, which have the structure ##STR1## wherein: R, same or different, is hydrogen, lower alkyl, lower alkylidene, lower alkenyl, allyl or aryl;

Method for detecting cations in a test sample utilizing chromogenic

An improved process for preparing a 1-aminomethyl-6-substituted-4H-s-triazolo[4,3-a][1,4]benzodiazepine product, e.g., adinazolam, directly from the corresponding 1-hydrogen-6-substituted-4H-s-triazolo[4,3-a][1,4]benzodiazepine starting material, e.g., from estazolam, by conducting the reaction between the estazolam-type compound and the dimethylaminomethylene salt in the selected solvent in the presence of an alkali metal carbonate, and thereafter extracting the 1-aminomethyl-6-substituted-4H-s-triazolo[4,3-a]-[1,4]benzodiazepine from an aqueous organic solvent mixture thereof into a halogenated C.sub.1 to C.sub.3 -alkane solvent while maintaining the pH of the aqueous phase between pH 3.0 and 4.0, and thereafter recovering the product from the halogenated alkane solvent.

Preparing

Multiheteromacrocycles are disclosed that contain as part of the macrocycle, assemblies of 2,6-dimethylylpyridine (and their corresponding amine oxides), 2,5-dimethylylfuran, 2,5-dimethylyltetrahydrofuran, Diels-Alder adducts of 2,5-dimethylylfuran (and their reduction products), 2- and 4-substituted 1,3-dimethylbenzenes, pentamethylene, or p-phenylene coupled through oxygen to one another, or to ethylene, o-phenylene, or 1,1-binaphthyl-2,2- units (always coupled through oxygens) to form multidentate ligands for complexing selectively alkylammonium or metal cations.

Certain multioxymacrocycle compounds containing pyridyl as part of the

Multiheteromacrocycles are disclosed that contain as part of the macrocycle, assemblies of 2,6-dimethylylpyridine (and their corresponding amine oxides), 2,5-dimethylylfuran, 2,5-dimethylyltetrahydrofuran, Diels-Alder adducts of 2,5-dimethylylfuran (and their reduction products), 2- and 4-substituted 1,3-dimethylylbenzenes, pentamethylene, or p-phenylene coupled through oxygen to one another, or to ethylene, o-phenylene, or 1,1-binaphthyl-2,2- units (always coupled through oxygens) to form multidentate ligands for complexing selectively alkylammonium or metal cations.

Multioxymacrocycle compounds containing pyridyl rings as part of the

Chiral, hinged, asymmetric host binaphthyl-based multiheteromacrocycles of oxygen covalently bonded to styrene/divinylbenzene copolymers are provided. These new compounds have specific chiral recognition properties, which properties make these new compounds useful for separating or resolving racemic and other mixtures of amino acids, amino acid esters and salts thereof for either or both of analytical purposes or large scale manufacturing procedures.

Polymer-multiheteromacrocycles

Chiral, hinged and functionalized host multiheteromacrocycles of the oxygen, nitrogen and sulfur-containing type are disclosed possessing holes sized to afford selective complexation of specific guest substances and shapes to recognize chirally guest molecules by virtue of the chiral steric barrier of the 2,2'-diheteroatom-1,1'-binaphthyl grouping, the naphthyl-naphthyl dihedral angle, and the provision of ortho positioned side chain substituents (arms) bearing terminal functional groups which act as counterions or additional complexing sites, and the provision of remote position side chain substituents used to control solubility and volatility properties or to bond the multiheteromacrocycles to solid supports.

Asymmetric macrocycles containing oxygen and binaphthyl ring members

Multiheteromacrocycles are disclosed that contain as part of the macrocycle, assemblies of 2,6-dimetylylpyridine (and their corresponding amine oxides), 2,5-dimethylylfuran, 2,5-dimethylyltetrahydrofuran, Diels-Alder adducts of 2,5-dimethylylfuran (and their reduction products), 2- and 4-substituted 1,3-dimethylylbenzenes, pentamethylene, or p-phenylene coupled through oxygen to one another or to ethylene, o-phenylene, or 1,1-binaphthyl-2,2- units (always coupled through oxygens) to form multidentate ligands for complexing selectively alkylammonium or metal cations.

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Los Angeles, CA, United States of America

Donald J Cram