Patents Assigned to Research Institute for Medicine and Chemistry
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Patent number: 7235552Abstract: Novel sterol derivatives of formula (I), in which: R1 represents a hydroxyl group or protected hydroxyl group, R2 represents a hydrogen atom and a double bond is present at c, or R1 and R2 together represent an oxo group and a double bond is present at b or double bonds are present at a and b; R3 represents a methyl group having ?- or ?-configuration; R4 and R5, which may be the same or different, are selected from hydrogen atoms and aliphatic, cycloaliphatic, araliphatic and aryl groups, or together with the nitrogen atom to which they are attached form a heterocyclic group; and X represents a polymethylene group containing 2–5 carbon atoms, an oxa group-containing analogue thereof in which a methylene group other than that attached to the —CO.NR4R5 moiety is replaced by an oxygen atom, or an unsaturated analogue thereof containing up to two double bonds.Type: GrantFiled: August 1, 2000Date of Patent: June 26, 2007Assignee: Research Institute for Medicine and Chemistry, Inc.Inventors: Robert Henry Hesse, Sundara Katugam Srinivasasetty Setty, Malathi Ramgopal
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Patent number: 6967195Abstract: Compounds of formula (I) in which: R1 represents a hydrogen atom or an O-protecting group; R2 represents a hydroxyl, lower alkoxy, carboxaldehyde, lower alk-1-enyl or hydroxy- or lower alkoxy-substituted lower alkyl group; R3 represents a methyl group having ?- or ?-configuration; X represents a C1-3 alkylene group or a valence bond; Y represents a carboxaldehyde group or a group of formula —C(R4)(R5)OR1 where R1 is as defined above and R4 and R5, which may be the same or different, are each selected from hydrogen atoms, alkyl, alkenyl and alkynyl groups such that the total carbon content of R4 and R5 does not exceed three atoms, with the proviso that X is a valence bond when both R4 and R5 are other than hydrogen; and the dotted line signifies that a double bond may optionally be present at the 16(17)-position exhibit potent cell modulating activity, including antiproliferative and antiangiogenic effects.Type: GrantFiled: May 11, 2001Date of Patent: November 22, 2005Assignee: Research Institute for Medicine and Chemistry, Inc.Inventors: Robert Henry Hesse, Sundara Katugam Srinivasasetty Setty, Maurice Murdoch Pechet, Michael Gile
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Publication number: 20050171075Abstract: Formula (I) in which: R1 and R2, which may be the same or different, each represents a lower alkyl, alkenyl or alkynyl group; R3 represents a methyl group having ?- or ?-configuration; R4 represents a hydrogen atom or an etherifying or esterifying group; R5 represents a hydrogen atom, a hydroxyl group or a lower alkoxy group; X represents a group OR4, or a group NR6R7 wherein R6 represents a hydrogen atom, an aliphatic or araliphatic group, or an acyl group comprising an aliphatic, araliphatic or aryl group linked to the nitrogen atom by way of a carbonyl group; and R7 is a hydrogen atom or a lower alkyl group; Y represents a lower alkylene, alkenylene or alkynylene group optionally substituted by a hydroxyl, etherified hydroxyl or esterified hydroxyl group; exhibit potent effects on modulation of cell growth and differentiation, while having low calcaemic activity.Type: ApplicationFiled: February 11, 2005Publication date: August 4, 2005Applicant: Research Institute for Medicine and Chemistry Inc.Inventors: Robert Hesse, Sundara Srinivasasetty Setty, Malathi Ramgopal, Sanga Kugabalnsooriar
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Patent number: 6881730Abstract: Compounds of Formula (I) in which: R1 and R2, which may be the same or different, each represents a lower alkyl, alkenyl or alkynyl group; R3 represents a methyl group having ?- or ?-configuration; R4 represents a hydrogen atom or an etherifying or esterifying group; R5 represents a hydrogen atom, a hydroxyl group or a lower alkoxy group; X represents a group OR4, wherein R4 is as defined above, or a group NR6R7 wherein R6 represents a hydrogen atom, an aliphatic or araliphatic organic group, or an acyl group comprising an aliphatic, araliphatic or aryl organic group linked to the nitrogen atom by way of a carbonyl group; and R7 is a hydrogen atom or a lower alkyl group; Y represents a lower alkylene, alkenylene or alkynylene group optionally substituted by a hydroxyl, etherified hydroxyl or esterified hydroxyl group; and the dotted lines signify that double bonds may be present at the 16(17)-position and/or either at the 6(7)- and 8(9)-positions or at the 7(8)-position exhibit potent effects on modulation ofType: GrantFiled: May 11, 2003Date of Patent: April 19, 2005Assignee: Research Institute for Medicine & Chemistry, Inc.Inventors: Robert Henry Hesse, Sundara Katugam Srinivasasetty Setty, Malathi Ramgopal, Sanga Kugabalnsooriar
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Publication number: 20020188142Abstract: 1-Hydroxy pregnacalciferol derivatives of formula (I) and their corresponding 5,6-trans isomers wherein R1 is hydroxyl or lower alkoxy and R2 is optionally hydroxylated or lower alkoxylated lower alkynyl and R1 is C(RA) (RB)CH3 where RA is optionally hydroxylated or lower alkoxylated lower alkynyl and RB is hydroxyl or lower alkoxy or RA and RB together represent oxo and R2 is hydrogen, hydroxyl or lower alkoxy, and R3 and R4 represent hydrogen atoms, exhibit anti-progesterone activity and may be useful as antineoplastic, antifertility, antiproliferative, immunosuppressive and/or antiinflammatory agents.Type: ApplicationFiled: March 7, 2002Publication date: December 12, 2002Applicant: Research Institute for Medicine and ChemistryInventors: Robert Henry Hesse, Maurice Murdoch Pechet, Sundara Katugam Srinivasasetty Setty
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Patent number: 6372926Abstract: 1-Hydroxy pregnacalciferol derivatives of formula (I) and their corresponding 5,6-trans isomers wherein R1 is hydroxyl or lower alkoxy and R2 is optionally hydroxylated or lower alkoxylated lower alkynyl or R1 is C(RA) (RB)CH3 where RA is optionally hydroxylated or lower alkoxylated lower alkynyl and RB is hydroxyl or lower alkoxy or RA and RB together represent oxo and R2 is hydrogen, hydroxyl or lower alkoxy, and R3 and R4 represent hydrogen atoms, exhibit anti-progesterone activity and may be useful as antineoplastic, antifertility, antiproliferative, immunosuppressive and/or antiinflammatory agents.Type: GrantFiled: February 19, 1999Date of Patent: April 16, 2002Assignee: Research Institute for Medicine and ChemistryInventors: Robert Henry Hesse, Maurice Murdoch Pechet, Sundara Katugam Srinivasasetty Setty
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Patent number: 6013814Abstract: The present invention relates to novel 1.alpha.-hydroxy vitamin D derivatives in which the 17-position side chain carries an azide or optionally substituted 1,2,3-triazole group, including compounds of general formula (I) where R.sup.1 represents a methyl group having .alpha.- or .beta.-configuration; W represents a valence bond or a C.sub.1-5 alkylene group; X represents azide or an optionally substituted triazole group; and A.dbd. represents a cyclohexylidene moiety characteristic of the A-ring of a 1.alpha.-hydroxylated vitamin D or analogue thereof. Active compounds of the invention exhibit cell modulating activity while exhibiting a substantial lack of calcaemic effect.Type: GrantFiled: October 20, 1998Date of Patent: January 11, 2000Assignee: Research Institute for Medicine and Chemistry, Inc.Inventors: Robert Henry Hesse, Sundara Katugam Srinivasasetty Setty, Malathi Ramgopal, Gaddam Subba Reddy
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Patent number: 5872140Abstract: The present invention relates to novel 1.alpha.-hydroxy vitamin D derivatives in which the 17-position side chain carries an azide or optionally substituted 1,2,3-triazole group, including compounds of general formula (I) where R.sup.1 represents a methyl group having .alpha.- or .beta.-configuration; W represents a valence bond or a C.sub.1-5 alkylene group; X represents azide or an optionally substituted triazole group; and A=represents a cyclohexylidene moiety characteristic of the A-ring of a 1.alpha.-hydroxylated vitamin D or analogue thereof. Active compounds of the invention exhibit cell modulating activity while exhibiting a substantial lack of calcaemic effect.Type: GrantFiled: March 21, 1996Date of Patent: February 16, 1999Assignee: Research Institute for Medicine and Chemistry, Inc.Inventors: Robert Henry Hesse, Sundara Katugam Srinivasasetty Setty, Malathi Ramgopal, Gaddam Subba Reddy
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Patent number: 5811562Abstract: The present invention relates to compounds of general formula (I) ##STR1## where R.sup.1 and R.sup.2, which may be the same or different, each represent a hydrogen atom or an aliphatic, cycloaliphatic, araliphatic or aryl group or together with the nitrogen atom to which they are attached form a heterocyclic group; R.sup.3 represents a methyl group having .alpha.- or .beta.-configuration; one of R.sup.a and R.sup.b represents a hydroxy group or protected hydroxy group and the other represents a hydrogen atom; Y represents a valence bond or an alkylene group containing up to 3 carbon atoms; and A= represents a cyclohexylidene moiety characteristic of the A-ring of a 1.alpha.-hydroxylated vitamin D or analogue thereof. Active compounds of the invention exhibit separation of cell modulating and calcaemic activities coupled with enhanced duration of activity.Type: GrantFiled: November 20, 1996Date of Patent: September 22, 1998Assignee: Research Institute for Medicine and Chemistry Inc.Inventors: Robert Henry Hesse, Sundara Katugam Srinivasasetty Setty
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Patent number: 5786347Abstract: The invention relates to vitamin D amine and amide derivatives of general formula ##STR1## where R represents a hydrogen atom, an aliphatic, cycloaliphatic or araliphatic group, or an acyl group comprising an aliphatic, cycloaliphatic, arylaliphatic or aryl group linked to the nitrogen atom by way of a carbonyl group; R.sup.1 and R.sup.2 are each selected from lower alkyl and cycloalkyl groups or together with the carbon atom to which they are attached form a lower cycloalkyl group; R.sup.3 represents a methyl group having .alpha.- or .beta.-configuration; Y represents a lower alkylene, alkenylene or alkynylene group optionally substituted by a hydroxyl, etherified hydroxyl or esterified hydroxyl group; and A.dbd. represents a cyclohexylidene moiety characteristic of the A-ring of a 1 .alpha.-hydroxylated vitamin D or analogue thereof. Active compounds of the invention exhibit cell modulating activity and in certain cases may also have an effect on calcium metabolism.Type: GrantFiled: July 31, 1996Date of Patent: July 28, 1998Assignee: Research Institute for Medicine and Chemistry, Inc.Inventors: Robert Henry Hesse, Sundara Katugam Srinivasaetty Setty, Malathi Ramgopal
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Patent number: 5756733Abstract: The invention relates to novel 1.alpha.-hydroxy vitamin D derivatives and their 20-epi analogues, comprising compounds of general formula (I) ##STR1## where R.sup.1 and R.sup.2, which may be the same or different, each represents a hydrogen atom or an aliphatic, cycloaliphatic, araliphatic or aryl group or together with the nitrogen atom to which they are attached form a heterocyclic group; R.sup.3 represents a methyl group having .alpha.- or .beta.-configuration; X represents a valence bond or a C.sub.1-2 alkylene group; Y represents --O--, --S--, --CH.sub.2 -- or --NR-- where R is a hydrogen atom or an organic group; Z represents a valence bond or a C.sub.1-3 alkylene group; and A.dbd. represents a cyclohexylidene moiety characteristic of the A-ring of a 1.alpha.-hydroxylated vitamin D or analogue thereof, with the proviso that when --X--Y--Z-- together represent an alkylene group containing up to 4 carbon atoms A.dbd. does not carry an exocyclic methylene group at the 10-position.Type: GrantFiled: January 5, 1996Date of Patent: May 26, 1998Assignee: Research Institute for Medicine and ChemistryInventors: Robert Henry Hesse, Sundara Katugam Srinivasasetty Setty, Malathi Ramgopal
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Patent number: 5686435Abstract: The invention pertains to vitamin D amide derivatives of formula (I). These novel 1.alpha.-hydroxy vitamin D derivatives and their 20-epi analogues comprise compounds of formula (I) and corresponding 5,6-trans isomers, where Y represents an alkylene or alkenylene group containing up to four carbon atoms; R.sup.1 and R.sup.2 independently represent a hydrogen atom or a lower alkyl or cycloalkyl group, or R.sup.1 R.sup.2 N-- represents a heterocyclic group; and R.sup.3 and R.sup.4 independently represent a hydrogen atom or an O-protecting group. Active compounds, in which R.sup.3 and R.sup.4 are hydrogen atoms or metabolically labile O-protecting groups exhibit potent cell modulating effect, but minimal effect on calcium metabolism.Type: GrantFiled: December 7, 1995Date of Patent: November 11, 1997Assignee: Research Institute for Medicine and ChemistryInventors: Robert Henry Hesse, Gaddam Subba Reddy, Sundara Katugam Srinivasasetty Setty
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Patent number: 5494905Abstract: The invention pertains to vitamin D amide derivatives of formula (I). These novel 1.alpha.-hydroxy vitamin D derivatives and their 20-epi analogues comprise compounds of formula (I) and corresponding 5,6-trans isomers, where Y represents an alkylene or alkenylene group containing up to four carbon atoms; R.sup.1 and R.sup.2 independently represent a hydrogen atom or a lower alkyl or cycloalkyl group, or R.sup.1 R.sup.2 N-- represents a heterocyclic group; and R.sup.3 and R.sup.4 independently represent a hydrogen atom or an 0-protecting group. Active compounds, in which R.sup.3 and R.sup.4 are hydrogen atoms or metabolically labile 0-protecting groups exhibit potent cell modulating effect, but minimal effect on calcium metabolism.Type: GrantFiled: May 31, 1994Date of Patent: February 27, 1996Assignee: Research Institute for Medicine and ChemistryInventors: Robert H. Hesse, Gaddam S. Reddy, Sundara K. S. Setty
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Patent number: 5472957Abstract: The invention provides novel compositions for use in pharmaceutical and veterinary medicine which contain 1.alpha.-hydroxy vitamin D compounds. Particular compositions are described which contain steroids which induce or assist in combatting osteoporosis together with 1.alpha.-hydroxy vitamin D.sub.3 or 1.alpha.,25-dihydroxy vitamin D.sub.3. Methods of treatment of diseases are also provided including many which are resistant to vitamin D.sub.3, in particular bone diseases.Type: GrantFiled: August 10, 1993Date of Patent: December 5, 1995Assignee: Research Institute for Medicine and ChemistryInventors: Robert H. Hesse, Ezio Rizzardo, Derek H. R. Barton
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Patent number: 4772433Abstract: Compounds of the general formula ##STR1## wherein R represents a hydrogen atom or a hydroxyl protecting group, Y represents a hydrogen atom or an optionally protected hydroxyl group, X represents the residue of a dienophile and either R.sup.1 represents a halogen atom a hydrocarbylsulphonyloxy group or a group of the formula --Z--R.sup.3 (in which Z represents --O--, --S--, --SO--, --NR.sup.4 -- or --CR.sup.4 R.sup.5 -- and R.sup.3, R.sup.4 and R.sup.5, which may be the same or different, each represent a hydrogen atom or a straight or branched aliphatic group having 1-12 carbon atoms and which may optionally carry one or more substituents) and R.sup.2 represents a hydrogen atom or R.sup.1 and R.sup.2 together represent an oxo group or an optionally substituted alkylidene group, except that R.sup.1 and R.sup.2 together with the group --CH(CH.sub.3)CH-- to which they are attached do not represent a group having the branched 17.beta.-hydrocarbyl side chain skeleton of vitamin D.sub.2 or vitamin D.sub.Type: GrantFiled: February 10, 1986Date of Patent: September 20, 1988Assignee: Research Institute for Medicine and Chemistry Inc.Inventor: Robert Hesse
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Patent number: 4554105Abstract: 1-unsubstituted 5,6-trans vitamin D compounds are 1.alpha.-hydroxylated by Se.sup.IV oxidation in the presence of selenous acid at a pH in the range 3-9. The oxidation is preferably effected using a 1-unsubstituted-3-trihydrocarbylsilyloxy-5,6-trans vitamin D compound in the presence of a co-oxidant.Type: GrantFiled: September 7, 1984Date of Patent: November 19, 1985Assignee: Research Institute For Medicine and Chemistry Inc.Inventor: Robert H. Hesse
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Patent number: 4284558Abstract: Saturated organic compounds containing a hydrogen atom bound to a tertiary carbon atom may be electrophilically fluorinated by reaction with an electrophilic fluorinating agent such as molecular fluorine or trifluoromethyl hypofluorite under conditions whereby the formation of free fluorine radicals is suppressed, e.g. by the presence of a free radical inhibitor such as oxygen or nitrobenzene, the reactants being substantially homogeneously dispersed in a liquid medium, e.g. a solvent medium such as fluorotrichloromethane or chloroform/fluorotrichloromethane, so that the said hydrogen atom is electrophilically replaced by a fluorine atom. The fluorination is highly selective and, in the case of complex substrates such as saturated steroids which contain a number of tertiary C--H bonds, may be substantially completely confined to replacement of the hydrogen atom at the tertiary carbon atom which has the highest electron density about the C--H bond.Type: GrantFiled: March 9, 1977Date of Patent: August 18, 1981Assignee: Research Institute for Medicine and Chemistry, Inc.Inventors: Derek H. R. Barton, Robert H. Hesse
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Patent number: 4263215Abstract: 1-Hydroxy-5,6-trans vitamin D compounds are prepared by oxidizing a 5,6-trans vitamin D compound using a selenic ester which may be formed in situ using selenous acid or selenium dioxide in the presence of an alcohol.Type: GrantFiled: November 6, 1979Date of Patent: April 21, 1981Assignee: Research Institute for Medicine and Chemistry, Inc.Inventors: Robert H. Hesse, Graham Johnson
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Patent number: 4234515Abstract: N,N-difluoroamines are prepared by fluorination of compounds containing a >C.dbd.N-- bond using molecular fluorine or a hypofluorite in which the fluoroxy group is bonded to an inert electron attracting group, such hypofluorites including fluoroalkyl hypofluorites such as trifluoromethyl hypofluorite. The fluorination is advantageously conducted in the presence of an alkanol or other nucleophilic compound. Suitable starting materials include imino ethers and esters and aliphatic and aromatic Schiff's bases, use of the latter being particularly convenient.Type: GrantFiled: May 9, 1978Date of Patent: November 18, 1980Assignee: Research Institute for Medicine & Chemistry Inc.Inventors: Derek H. R. Barton, Robert H. Hesse
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Patent number: 4181655Abstract: Novel compounds of general formula ##STR1## (where R.sup.1 and R.sup.2, which may be the same or different, are hydrogen atoms or alkyl groups; and R.sup.3 and R.sup.4, which may be the same or different, represent alkyl groups which may carry substituents, R.sup.4 alternatively representing a hydrogen atom; or R.sup.3 and R.sup.4 together with the intervening N represent a heterocyclic group or an acid-addition salt thereof) are provided, together with a process for their preparation. The new compounds are useful as antidepressants.Type: GrantFiled: May 4, 1977Date of Patent: January 1, 1980Assignee: Research Institute for Medicine and Chemistry Inc.Inventors: Derek H. R. Barton, Robert H. Hesse