Patents Assigned to Interx Research Corporation
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Patent number: 4174450Abstract: This invention deals with chemical intermediates having the formula ##STR1## wherein R.sub.1 and R.sub.2 together with the carbon atom to which they are attached form a single hetero atom member selected from the group consisting of a five-to seven-membered heterocycle containing one hetero-N-atom and a N-substituted five-to seven-membered heterocycle containing an hetero-N-atom whose substituent is C.sub.1 -C.sub.2 alkyl. These compounds are useful in the synthesis of compounds having a variety of uses as pharmaceuticals.Type: GrantFiled: November 8, 1976Date of Patent: November 13, 1979Assignee: INTERx Research CorporationInventors: Nicolae S. Bodor, Sun-Shine Yuan
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Patent number: 4171452Abstract: There is provided, a novel class of compounds exhibiting antibacterial activity and having the formula: ##STR1## wherein X and Y each represent a member which may be the same or different selected from the group consisting of H and Cl with the proviso that X and Y cannot represent H simultaneously;R.sub.1 and R.sub.2 each represent a member which may be the same or different selected from the group consisting of an n- or branched alkyl group of from 1 to 20 carbon atoms, an aryl group (phenyl, naphthyl, etc.) and ##STR2## WHEREIN M REPRESENTS AN INTEGER OF FROM 2 TO 5; N REPRESENTS AN INTEGER OF 1 TO 8; AND Z represents a member selected from the group consisting of an --OOCR.sub.3 group, an --OR.sub.3 group and an --OCH.sub.2 OR.sub.3 group,Wherein R.sub.3 represents a member selected from the group consisting of an n- or branched alkyl group of 1 to 20 carbon atoms, a phenyl group, a naphthyl group, a benzyl group, ##STR3##WHEREIN X is a halogen atom (Cl, Br, I), ##STR4##WHEREIN R.sub.Type: GrantFiled: May 16, 1977Date of Patent: October 16, 1979Assignee: INTERx Research CorporationInventors: James J. Kaminski, Nicolae S. Bodor
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Patent number: 4169147Abstract: There is provided, novel, transient, pro-drug forms of phenylbutazone and oxyphenbutazone having the following formula: ##STR1## wherein R represents a member selected from the group consisting of a C.sub.1 -C.sub.2 O-alkylsulfonyl group, an aryl(phenyl, p-tolyl, naphthyl)sulfonyl group, a nicotinoyl group, an iso-nicotinoyl group, a picolinoyl group, an N-protected naturally occurring amino acid residue, wherein the protective group on the amino group of the amino acid residue is removable via hydrogenolysis or hydrolysis, and an amino acid residue containing a C.sub.1 -C.sub.2 N,N-dialkylamino or a C.sub.4 -C.sub.6 cycloalkylamino group. ##STR2## wherein X and Y each represent a member selected from the group consisting of a hydrogen atom and a --OR.sub.1 group, with the proviso that either X or Y is a hydrogen atom and that R.sub.2 is a member selected from the same or different groups represented by R.sub.1 ; and wherein R.sub.Type: GrantFiled: October 7, 1977Date of Patent: September 25, 1979Assignee: INTERx Research CorporationInventors: Nicholas S. Bodor, Kenneth B. Sloan
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Patent number: 4163058Abstract: Novel derivatives of 5,5-diphenylhydantoin, having the formula: ##STR1## wherein R is as defined in the specification and claims hereinafter, are disclosed. These compounds exhibit enhanced solubility over diphenylhydantoin per se and find therapeutic usefulness as anticonvulsants, antiepileptics and antiarrhythmics.Type: GrantFiled: April 22, 1977Date of Patent: July 31, 1979Assignee: INTERX Research CorporationInventors: Valentino J. Stella, Kenneth B. Sloan
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Patent number: 4160099Abstract: Labile quaternary ammonium salts of the following formula (I) and (II) are provided: ##STR1## wherein ##STR2## represents a tertiary aliphatic amine; wherein ##STR3## represents an unsaturated amine; wherein R represents a member selected from the group consisting of a hydrogen atom, a C.sub.1 -C.sub.8 open chain or cyclo alkyl group, a C.sub.1 -C.sub.8 alkoxyalkyl group, a C.sub.1 -C.sub.8 acyloxyalkyl group, a C.sub.1 -C.sub.8 haloalkyl group, a C.sub.1 -C.sub.8 carboxyalkyl group, a C.sub.2 -C.sub.8 alkenylphenyl group, an aryl group, and a substituted aryl group, whose substituents are selected from the group consisting of a halogen atom, an O-lower alkyl (C.sub.1 -C.sub.4) group, an O-acyl group, a nitro group, a carboxyl group, and a carboethoxy group; wherein R.sub.1 which may be the same or different, represents any member defined by R above with the proviso that R.sub.Type: GrantFiled: September 20, 1976Date of Patent: July 3, 1979Assignee: Interx Research CorporationInventor: Nicolae S. Bodor
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Patent number: 4158005Abstract: Optically and therapeutically active compounds of the formula: ##STR1## wherein R represents a member selected from the group consisting of a straight or branched alkyl group of from one to twenty carbon atoms (C.sub.1 -C.sub.5 being preferred), an ethoxycarbonyl group, a benzyloxycarbonyl group, a phenyl group, an ##STR2## WHEREIN R is as defined above and R.sub.3 is a member selected from the group consisting of a hydrogen atom, a methyl group and a phenyl group, and a 2-, 3-, or 4-pyridyl group, or the HX salts thereof, wherein X represents a pharmaceutically acceptable acid addition salt anion, are prepared optically active m-hydroxy-.alpha.-[methylamino)methyl]benzyl alcohol (phenylephrine).The compounds prepared by the process of this invention find therapeutic application to warm-blooded animals (e.g., humans) in the management of asthma, nasal congestion and as decongestants, vasoconstrictors, mydriatic agents, and anti-glaucomatous agents in the practice of ophthalmology.Type: GrantFiled: May 9, 1977Date of Patent: June 12, 1979Assignee: Interx Research CorporationInventors: Nicolae S. Bodor, Sun-Shine Yuan
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Patent number: 4154824Abstract: Potassium is rendered nonbitter tasting by combining the same with phytic acid. The final product is useful as a nonbitter tasting potassium supplement for warm-blooded animals deficient in levels of potassium.Type: GrantFiled: July 20, 1976Date of Patent: May 15, 1979Assignee: INTERx Research CorporationInventors: Nicolae S. Bodor, Takeru Higuchi
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Patent number: 4147768Abstract: Therapeutic and undegraded levels of digoxin in warm-blooded animals are achieved by orally admininstering thereto, a non-toxic pharmaceutical enteric-coated tablet comprising:(a) A cardiotonic effective amount of digoxin;(b) a non-toxic pharmaceutically acceptable inert diluent, and(c) a standard non-toxic pharmaceutically acceptable enteric coating.This composition is extremely useful in the treatment of cardiac insufficiency in warm-blooded animals. When administered to warm-blooded animals (e.g., humans), superior therapeutic and undegraded blood levels of digoxin are observed over that normally observed with conventional solid dosage formulations for oral administration.Type: GrantFiled: May 19, 1978Date of Patent: April 3, 1979Assignee: Interx Research CorporationInventors: Richard D. Shaffer, John J. Windheuser
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Patent number: 4145441Abstract: Compounds having the formula: ##STR1## wherein R represents hydrogen or a straight or branched C.sub.1 -C.sub.5 alkyl group; and R.sub.1 and R.sub.2 which may be the same or different represent an acyl member which is alkanoyl having 1-22 carbon atoms, alkenoyl having one or two double bonds and having 4-22 carbon atoms, cycloalkyl-C.sub.n H.sub.2n ##STR2## having a total of 4-10 carbon atoms of which 3-7 are ring carbon atoms in cycloalkyl and wherein n is zero, one, or two, phenoxyacetyl, naphthalenecarbonyl, pyridinecarbonyl, phenyl-C.sub.n H.sub.2n ##STR3## wherein n is zero, one or two and phenyl is unsubstituted or is substituted by 1-3 alkyl having 1-4 carbon atoms, alkoxy having 1-4 carbon atoms, halo, trifluoromethyl, dialkylamino having 2-8 carbon atoms, or alkanoylamino having 1-6 carbon atoms groups; ##STR4## wherein R.sub.3 may be hydrogen, hydroxyl or a member defined in accordance with R.sub.1 and R.sub.2 above or ##STR5## wherein R.sub.8 and R.sub.Type: GrantFiled: November 4, 1977Date of Patent: March 20, 1979Assignee: Interx Research CorporationInventor: Nicholas S. Bodor
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Patent number: 4140796Abstract: Free and conjugated bile acids are effectively bound in warm-blooded animals by administering thereto, a therapeutically effective bile acid binding amount of a quaternary ammonium compound having the formula: ##STR1## wherein ##STR2## represents a tertiary open chain or cyclic aliphatic amine; wherein ##STR3## represents an unsaturated amine; wherein R represents a member selected from the group consisting of a hydrogen atom, a C.sub.1 -C.sub.20 open chain or cyclo alkyl group, a C.sub.1 -C.sub.20 alkoxy-alkyl group, a C.sub.1 -C.sub.20 alkanoyloxyalkyl group, a C.sub.1 -C.sub.20 haloalkyl group, a C.sub.1 -C.sub.20 carboxyalkyl group, an aryl group, and a substituted aryl group, whose substituents are selected from the group consisting of a halogen atom, an O--C.sub.1 -C.sub.4 alkyl group, an O--C.sub.1 -C.sub.8 alkanoyl group, a nitro group, a carboxyl group, and a carboethoxy group; wherein R.sub.Type: GrantFiled: June 24, 1977Date of Patent: February 20, 1979Assignee: INTERx Research CorporationInventor: Nicolae S. Bodor
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Patent number: 4139709Abstract: The compound 1,2-Diphenyl-3,5-ditrifluoroacetyloxy-4-butyl-5-hydroxy-3-pyrazoline is disclosed as an intermediate useful in the preparation of selected pro-phenylbutazone derivatives.Such selected pro-phenylbutazone derivatives are novel, transient, pro-drug forms of phenylbutazone and oxyphenbutazone having the following formulae wherein R, R.sub.2, R.sub.4, R.sub.5, X and Y are as defined herein: ##STR1## The above-identified compounds exhibit anti-inflammatory activity in warm-blooded animals. Upon administration to warm-blooded animals, these compounds pass through the gastrointenstinal tract and cleave in the bloodstream, thus releasing phenylbutazone or oxyphenbutazone in an anti-inflammatory effective amount at their therapeutic site or sites of activity.Type: GrantFiled: March 14, 1977Date of Patent: February 13, 1979Assignee: INTERx Research CorporationInventors: Nicolae S. Bodor, Kenneth B. Sloan
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Patent number: 4132805Abstract: There is provided, a novel class of compounds exhibiting antibacterial activity and having the formula: ##STR1## wherein X and Y each represent a member which may be the same or different selected from the group consisting of H and Cl with the proviso that X and Y cannot represent H simultaneously; R.sub.1 and R.sub.2 each represent a member which may be the same or different selected from the group consisting of an n- or branched alkyl group of from 1 to 20 carbon atoms, an aryl group (phenyl, naphthyl, etc.) and a ##STR2## WHEREIN M REPRESENTS AN INTEGER OF FROM 2 TO 5; N REPRESENTS AN INTEGER OF 1 TO 8; AND Z represents a member selected from the group consisting of an --OOCR.sub.3 group, an --OR.sub.3 group and an --OCH.sub.2 OR.sub.3 group, wherein R.sub.Type: GrantFiled: October 3, 1977Date of Patent: January 2, 1979Assignee: INTERx Research CorporationInventors: James J. Kaminski, Nicolae S. Bodor
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Patent number: 4120959Abstract: Free and conjugated bile acids are effectively bound in warm-blooded animals by administering thereto, a therapeutically effective bile acid binding amount of a quaternary ammonium compound having the formula: ##STR1## wherein >N represents a tertiary open chain or cyclic aliphatic amine; wherein >N represents an unsaturated amine; wherein R represents a member selected from the group consisting of a hydrogen atom, a C.sub.1 -C.sub.20 open chain or cyclo alkyl group, a C.sub.1 -C.sub.20 alkoxyalkyl group, a C.sub.1 -C.sub.20 alkanoyloxyalkyl group, a C.sub.1 -C.sub.20 haloalkyl group, a C.sub.1 -C.sub.20 carboxyalkyl group, an aryl group, and a substituted aryl group, whose substituents are selected from the group consisting of a halogen atom, an O--C.sub.1 -C.sub.4 alkyl group, an O--C.sub.1 -C.sub.8 alkanoyl group, a nitro group, a carboxyl group, and a carboethoxy group; wherein R.sub.Type: GrantFiled: June 24, 1977Date of Patent: October 17, 1978Assignee: Interx Research CorporationInventor: Nicolae S. Bodor
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Patent number: 4120958Abstract: There is provided, a novel 2-acetoxybenzoic acid-nicotinamide complex, which exhibits enhanced water solubility and dissolution characteristics, thus permitting rapid absorption of the 2-acetoxybenzoic acid through the gastrointestinal lining for attainment of exceptional 2-acetoxybenzoic acid blood levels.Type: GrantFiled: March 11, 1977Date of Patent: October 17, 1978Assignee: Interx Research CorporationInventor: Anwar A. Hussain
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Patent number: 4117232Abstract: Novel, transient pro-drug forms of the anti-inflammatories phenylbutazone and oxyphenbutazone are disclosed, the same having the structural formulae: ##STR1## wherein R is a member selected from the group consisting of C.sub.1 -C.sub.2 alkylsulfonyl, phenylsulfonyl, p-tolylsulfonyl and naphthylsulfonyl, and ##STR2## wherein X and Y each represent a member selected from the group consisting of a hydrogen atom and ##STR3## with the proviso that either X or Y is a hydrogen atom, R.sub.1 is selected from the group consisting of C.sub.1 -C.sub.2 alkylsulfonyl, phenylsulfonyl, p-tolylsulfonyl and naphthylsulfonyl, and R.sub.2 is selected from the group consisting of straight or branched chain C.sub.1 -C.sub.5 alkyl and phenyl.Type: GrantFiled: March 14, 1977Date of Patent: September 26, 1978Assignee: INTERx Research CorporationInventors: Nicolae S. Bodor, Kenneth B. Sloan
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Patent number: 4115588Abstract: There is provided, a novel class of compounds exhibiting antibacterial activity and having the formula: ##STR1## wherein X and Y each represent a member which may be the same or different selected from the group consisting of H and Cl with the proviso that X and Y cannot represent H simultaneously; R.sub.1 and R.sub.2 each represent a member which may be the same or different selected from the group consisting of an n- or branched alkyl group of from 1 to 20 carbon atoms, an aryl group (phenyl, naphthyl, etc.) and ##STR2## WHEREIN M REPRESENTS AN INTEGER OF FROM 2 TO 5; N REPRESENTS AN INTEGER OF 1 TO 8; AND Z represents a member selected from the group consisting of an --OOCR.sub.3 group, an --OR.sub.3 group and an --OCH.sub.2 OR.sub.3 group, wherein R.sub.3 represents a member selected from the group consisting of an n- or branched alkyl group of 1 to 20 carbon atoms, a phenyl group, a naphthyl group, a benzyl group, ##STR3## WHEREIN X is a halogen atom (Cl, Br, I), ##STR4## WHEREIN R.sub.Type: GrantFiled: June 6, 1977Date of Patent: September 19, 1978Assignee: INTERx Research CorporationInventors: James J. Kaminski, Nicolae S. Bodor
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Patent number: 4094983Abstract: Intraocular pressure in warm-blooded animals is reduced by topically applying to the eye thereof, an effective ophthalmologically acceptable amount of a compound of the formula: ##STR1## wherein R represents a member selected from the group consisting of hydrogen or a C.sub.1 -C.sub.5 straight or branched alkyl group; and wherein R.sub.1 and R.sub.Type: GrantFiled: January 17, 1977Date of Patent: June 13, 1978Assignee: Interx Research CorporationInventor: Nicholas S. Bodor
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Patent number: 4092420Abstract: There is provided, a novel class of compounds exhibiting antibacterial activity and having the formula: ##STR1## wherein X and Y each represent a member which may be the same or different selected from the group consisting of H and Cl with the proviso that X and Y cannot represent H simultaneously; R.sub.1 and R.sub.2 each represent a member which may be the same or different selected from the group consisting of an n- or branched alkyl group of from 1 to 20 carbon atoms, an aryl group (phenyl, naphthyl, etc.) and a ##STR2## WHEREIN M REPRESENTS AN INTEGER OF FROM 2 TO 5; N REPRESENTS AN INTEGER OF 1 TO 8; AND Z represents a member selected from the group consisting of an --OOCR.sub.3 group, an --OR.sub.3 group and an --OCH.sub.2 OR.sub.3 group, wherein R.sub.3 represents a member selected from the group consisting of an n- or branched alkyl group of 1 to 20 carbon atoms, a phenyl group, a naphthyl group, a benzyl group, ##STR3## WHEREIN X is a halogen atom (Cl, Br, I), ##STR4## WHEREIN R.sub.Type: GrantFiled: June 6, 1977Date of Patent: May 30, 1978Assignee: INTERx Research CorporationInventors: James J. Kaminski, Nicolae S. Bodor
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Patent number: 4088783Abstract: Compounds of the formula: ##STR1## wherein R represents a member selected from the group consisting of a straight or branched alkyl group of from one to twenty carbon atoms (C.sub.1 -C.sub.5 being preferred), an ethoxycarbonyl group, a benzyloxycarbonyl group, a phenyl group, an ##STR2## WHEREIN R is as defined above and R.sub.3 is a member selected from the group consisting of a hydrogen atom, a methyl group and a phenyl group, and a 2-, 3-, or 4-pyridyl group, or the HX salts thereof, wherein X represents a pharmaceutically acceptable acid addition salt anion, are extremely valuable in the treatment of conditions responsive to sympathomimetic agents.The compounds of this invention find therapeutic application to warm-blooded animals (e.g., humans) in the management of asthma, nasal congestion and as decongestants, vasoconstrictors, mydriatic agents, and anti-glaucomatous agents in the practice of opthalmology.Type: GrantFiled: October 18, 1976Date of Patent: May 9, 1978Assignee: INTERx Research CorporationInventors: Nicolae S. Bodor, Sun-Shine Yuan
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Patent number: 4085214Abstract: There is provided exceptionally stable and useful pro-drug forms of theophylline having the formula: ##STR1## wherein R represents a straight or branched phenylalkenyl group having 2-8 carbon atoms in the alkenyl portion.The compounds of this invention are useful in the treatment of asthma in warm-blooded animals. Upon administration, the compounds of this invention slowly go into solution and subsequently cleave prior to and/or during the absorption process, releasing theophylline in a sustained manner at a non-toxic, therapeutic level; that is, without the large blood level variations normally observed when theophylline per se is administered.Type: GrantFiled: October 18, 1976Date of Patent: April 18, 1978Assignee: INTERx Research CorporationInventors: Takeru Higuchi, Nicolae S. Bodor, Yu-Neng Kuo