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Process and intermediates for preparing a cyclohexylnitrile (Fri, 26 May 2006)
Patent 535657 A method for preparing a (,(-unsaturated cyclohexene dicarbonitrile of formula (B) is disclosed, wherein the method comprises dehydrating the 1,4-dicarbonitrile cyclohexene-1-ol of formula (C), wherein Ba(OH)2 is used as a base for dehydrating the compound of formula (C) , where Ar is an aromatic group.
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Process and intermediates for preparing a cyclohexylnitrile (Fri, 26 May 2006)
Patent 535656 A method for preparing a (,(-unsaturated cyclohexene carboxylic acid of formula (A) is disclosed, wherein the method comprises hydrolysing the (,(-unsaturated cyclohexene dicarbonitrile of formula (B), wherein the hydrolysis is carried out using thionyl chloride, where Ar is an aromatic group.
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Process and intermediates for preparing a cyclohexylnitrile (Fri, 26 May 2006)
Patent 535655 A method for preparing a 1,4-dicarbonitrile cyclohexan-1-ol cyclohexane-1-ol of formula (C) by cyanohydrin homologation of a cyclohexanone precursor is disclosed, wherein the method comprises cyanohydrin homologation of a cyclohexanone of formula (D), wherein the homologation is carried out using an alkali metal cyanide salt or a trialkylsilyl cyanide, where Ar is an aromatic group.
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Process and intermediates for preparing a cyclohexylnitrile (Fri, 26 Nov 2004)
Patent 519800 A method for preparing a cyclohexanoic acid of formula (I) by cyanohydrin homologation of a cyclohexanone precursor is disclosed, wherein the method comprises reducing a, (,(-unsaturated cyclohexene carboxylic acid of formula (A), wherein the double bond is reduced by catalytic homologation using a heavy metal catalyst and an ammonium carbonate, where Ar is an aromatic group.
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Salts of cis-[4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl) cyclohexan-1-carboxylate] (Fri, 30 May 2003)
Patent 515169 The sodium salt of cis-[-4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-carboxylate]. Also described is the ethylene diamine salt of cis-[-4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-carboxylate]. Also described is the tris(hydroxymethyl)aminomethane salt of cis-[-4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-carboxylate]. Also described is a pharmaceutical composition comprising the sodium salt of cis-[-4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-carboxylate] and a pharmaceutically acceptable excipient. Also described is a pharmaceutical composition comprising the ethylene diamine salt of cis-[-4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-carboxylate] and a pharmaceutically acceptable excipient. Also described is a pharmaceutical composition comprising the tris(hydroxymethyl)aminomethane salt of cis-[-4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-carboxylate] and a pharmaceutically acceptable excipient...
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Modified meningococcal fHBP polypeptides (Thu, 24 May 2012)
The factor H binding activity of meningococcal fHBP can be uncoupled from its bactericidal sensitivity. NMR studies have identified various amino acid residues involved in the fHBP/fH interaction and one or more of these residues is modified in a fHBP to reduce or eliminate its ability to bind to fH.
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Peptide deformylase inhibitors (Thu, 26 Jun 2014)
The present invention relates to {2-(alkyl)-3-[2-(5-fluoro-4-pyrimidinyl)hydrazino]-3- oxopropyl}hydroxyformamide compounds of Formula (I): or pharmaceutically acceptable salts thereof, corresponding pharmaceutical compositions, processes for making and use of such compounds in the inhibition of bacterial peptide deformylase (PDF) activity and in treatment methods for bacterial infections.
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PEPTIDE DEFORMYLASE INHIBITORS (Thu, 30 Oct 2014)
The present invention relates to {2-(alkyl)-3-[2-(5-fluoro-4-pyrimidinyl)hydrazino]-3-oxopropyl}hydroxyformamide compounds of Formula (I): embedded image or pharmaceutically acceptable salts thereof, corresponding pharmaceutical compositions, processes for making and use of such compounds in the inhibition of bacterial peptide deformylase (PDF) activity and in treatment methods for bacterial infections.
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TRI-SUBSTITUTED IMIDAZOLES HAVING MULTIPLE THERAPEUTIC PROPERTIES (Wed, 26 Aug 1998)
This compound has the formula I wherein R1 is an optionally substituted 4-pyridyl, pyrimidinyl, quinolyl, isoquinolinyl, quinazolin-4-yl, 1-imidazolyl or 1-benzimidazolyl; R4 is an optionally substituted phenyl, naphth-1-yl or naphth-2-yl and R2 is as defined in the specification. A pharmaceutical composition containing a compound of formula I useful in the treatment of a cytokine mediated disease is claimed.
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CRYSTALLINE (R)-MANDELATE SALT OF (1R,2S)-2-PHENYLCYCLOPROPYLAMINE (Thu, 01 Feb 2018)
Disclosed is a crystalline form of the (R)-mandelate salt of (1R, 2S)-2- phenylcyclopropylamine. Also disclosed is a method for resolving trans-2- phenylcyclopropylamine.
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CRYSTALLINE SALT FORM OF (S)-5-BENZYL-N-(5-METHYL-4-OXO-2,3,4,5-TETRAHYDROBENZO[B][1,4]OXAZEPIN-3-YL)-4H-1,2,4-TRIAZOLE-3-CARBOXAMIDE (Thu, 27 Jun 2019)
Disclosed is a novel salt form of (S)-5-benzyl-N-(5-methyl-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)-4H-1,2,4-triazole-3-carboxamide, in particular crystalline forms thereof and pharmaceutical compositions containing the same. Also disclosed are processes for the preparation thereof and methods for use thereof.
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Substituted bridged urea analogs as sirtuin modulators (Thu, 06 Jul 2017)
Provided herein are novel substituted bridged urea and related analogs and methods of use thereof. The sirtuin-modulating compounds may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders including, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benefit from increased mitochondrial activity. Also provided are compositions comprising a sirtuin-modulating compound in combination with another therapeutic agent. Figure 1. H-NMR Spectrum of Compound 1
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Process for preparing certain pyrrolo[3,4-b]quinolines, certain 1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-3,14(4H,12H)-diones, and certain 8-methyl-7-(oxopropyl)-indolizino[1,2-b]quinolin-9(11H)-ones (Tue, 26 Nov 1996)
This process for preparing a compound selected from the group consisting essentially of pyrrolo[3,4-b]quinolines, 1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-3,14(4H,12H)-diones, and 8-methyl-7-(oxopropyl)-indolizino[1,2-b]quinolin-9(11H)-ones, comprises the step of intramolecular [4+2] cycloaddition of the N-arylimidate portion of a compound of formula: where: X = OH,OAlCl2, Cl, Br, I, F, OR, OSO2CF3 or any good leaving group or H Y = H or Y,R1 = -OCH2O-; R1 = H, OH, or OR, where R is an ester protecting group; R2 = H, NO2, or a protected amine function; R3 = H, C2H5, or a trialkylsilyl; R4 = H or CH2COOEt; R5 = COOMe or tosyl; or R4 and R5 are joined together to form a substituted pyridone: where A = H, COOR, or a functionality for preparation of the hydroxymethyl(C-17) portion of an E ring lactone; and B = H, OH, an appropriate leaving group or a functionality for preparation of C-(18-21) of the E ring lactone portion of camptothecin; with the unactivated acetylene portion. ..
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Method for the synthesis of quinoline derivatives (Fri, 26 Apr 2002)
Patent 503307 A method for preparing a compound of formula (I) wherein: Ar is an optionally substituted phenyl group, or a naphthyl or C5-7 cycloalkdienyl group, or an optionally substituted single or fused ring heterocyclic group, having aromatic character, containing from 5 to 12 ring atoms and comprising up to 4 hetero-atoms in the or each ring selected from S, O, N; R is linear or branched C1-8 alkyl, C3-7 cycloalkyl, C4-7 cycloalkylalkyl, an optionally substituted phenyl group or a phenyl C1-6 alkyl group, an optionally substituted 5-membered heteroaromatic ring comprising up to 4 heteroatom selected from 0 and N, hydroxy C1-6 alkyl, di C1-6 alkylaminoalkyl, C1-6 acylaminoalkyl, C1-6 alkoxyalkyl, C1-6 alkylcarbonyl, carboxy, C1-6 alkoxycarbonyl, C1-6 alkoxycarbonyl C1-6 alkyl, aminocarbonyl, C1-6 alkylaminocarbonyl, di C1-6 alkylaminocarbonyl; or is a group -(CH2)p- when cyclized onto Ar, where p is 2 or 3; R1 and R2, which may be the same or different, are independently H or C1-6 linear or branched alkyl, or together form a -(CH2)n- group in which n represents 3, 4, or 5; or R1 together with R forms a group -(CH2)q-, in which q is 2, 3,4 or 5; R3 and R4, which may be the same or different, are independently H, C1-6 linear or branched alkyl, C1-6 alkenyl, aryl, C1-6 alkoxy, hydroxy, halogen, nitro, cyano, carboxy, carboxamido, sulphonamido, trifluoromethyl, amino, mono and di-C1-6 alkylamino, -O(CH2)rNT2, in which r is 2, 3, or 4 and T is C1-6 alkyl or both T together with the N from a heterocyclic group (A) or (B) in which u is 0, 1 or 2; -O(CH2)s-OW2 in which s is 2, 3, or 4 and W is C1-6 alkyl; hydroxyalkyl, mono-or di-alkylaminoalkyl, acylamino, alkylsulphonylamino, aminoacylamino, mono- or di-alkylaminoacylamino; with up to 4 R3 substituents being present in the quinoline nucleus; or R4 is a group -(CH2)t- when cyclized onto R5 as aryl, in which t is 1, 2, or 3; and R5 is branched or linear C1-6 alkyl, C3-7 cycloalkyl, C4-7 cycloalkylalkyl, optionally substituted aryl, wherein the optional substituent is one of hydroxy, halogen, C1-6 alkoxy or C1-6 alkyl, or an optionally substituted single or fused ring heterocyclic group, having aromatic character, containing from 5 to 12 ring atoms and comprising up to four hetero-atoms in the or each ring selected from S, O, N; comprising: 1) adding a compound of formula (III) to base in a suitable solvent, to form a first reaction mixture, adding to the first reaction mixture a compound of formula (II) to form a second reaction mixture, and heating the second reaction mixture to form a compound of formula (IV); 2) isolating the compound of formula (IV) and then reacting the compound of formula (IV), in a suitable solvent, with a base to form a third reaction mixture, cooling the third reaction mixture, and adding carbonyl-activating agent to form a fourth reaction mixture; 3) adding a compound of formula (V) to the fourth reaction mixture to form a fifth reaction mixture; 4) heating the fifth reaction mixture; and 5) optionally converting the compound of formula (I) to a pharmaceutically acceptable salt thereof, wherein Ar, R, R1, R2, R3, R4, and R5 as used in a compound of formulae (II) through (VI) are as defined for a compound of formula (I)...
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SUBSTITUTED INDOLIZINO [1,2-B]QUINOLINONES (Tue, 28 May 1996)
These compounds, suitable for treating viral infections, are of the formula: where: R7 is -H, -NO2, -CN, C1-6 alkoxy, C1-6 alkyl, -OAr, -NHCH2Ar, -C���CCH2NRR1, -CH=CHCH2NRR1, or -(CH2)nCH2V; R9 is -H, -OR, -NO2, -NRR1, -CN, halo, or -(CH2)nCH2V; R10 is -H, -OR, -NO2, -NRR1, -CN, -COR12, -CH(OH)R12, -OC(O)R12, -OC(O)OR12, -OC(O)CH2CH2COOR13, -O-(CH2)1-5CH2NRR1, -OC(O)NRR1, 1,4'-bipiperidine-1'-carboxy, or -(CH2)nCH2V; each n = 0-3 and each V is independently -OH, -OC1-6alkyl, -OCOR12, -OCOOR13, -OCONRR1, -NRR1, or -CN; R11 is -H, -CN, or -OR; R12 is -H or C1-6alkyl; R13 is C1-6alkyl; R and R1 are independently selected from the group consisting of -H, -C1-6 alkyl, and, when R and R1 are substituted on nitrogen, R and R1 can be taken together to form a 5-7 membered saturated heterocyclic ring containing the nitrogen; X is -H, -OH, -CN, -SOR, -CH(OH)CH(OH)CH3, -CHR3R4, -C���CCH2NRR1, -CH2CH2CH2NRR1, C1-6alkyl, -C(CH2CH3)(OH)COOH, -C(R5)R6- or Y is -H, -CH3, or -CH2OR2; R2 is -H, -C(O)H, -C(O)C1-5alkyl, -C(O)C1-4alkylCOOH or -C(O)C1-4alkylNRR1; R3 is -OH, halo, or -NH2; R4 is -H, C1-6 alkyl, or -OR; R5 is =O, =NOH, or =CHR; R6 is -H, C1-6 alkyl, or -NRR1; and Ar is phenyl, monosubstituted phenyl, disubstituted phenyl, 3-pyridyl, monosubstituted 3-pyridyl, or disubstituted 3-pyridyl, where substituents can be -CN or C1-6 alkoxy; provided that: a) if one of R7, R9, R10 and R11 is other than -H, only one of the others may be other than -H; b) only one of R7, R9, R10 and R11 may be -NO2 or -NRR1; c) when X is -CHR3R4 and R4 is -OR, R3 is -OH; d) when R6 is -NRR1, R5 is =O; e) when R5 is =CHR, R6 is -H; f) when X is the moiety of formula II, R10 is -OH, R7, R9, and R11 are -H, and Y is -CH3; g) when Y is -CH2OR2, X is -C(R5)R6-, R5 is =O, and R6 is -H or C1-6 alkyl; h) when R7, R9, R10, and R11 are all -H and Y is -CH3, then X is not -H, -C(O)H, -CH2OH, -CH(OH)CH(OH)CH3, or -CH(OH)CH2CH3; i) when R7, R9, R10 and R11 are all -H and Y is -CH2OC(O)H, then X is not -C(O)CH2CH3; j) when R7, R9, R10, R11, and Y are all -H, then X is not -CH2OH, -C(O)H, -CH2Br, -OH, or -H; and k) when R7 is -OCH3, then X and Y are not -H...
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Process for making phenylthiomethylpyridinylalkenoates (Tue, 26 Nov 1996)
The specification describes a process for making phenylthiomethylpyridinylalkenoates of the formula or an N-oxide, or a pharmaceutically acceptable salt, where m is 0-5; R is C1 to C20-alphatic, unsubstituted or substituted phenyl-C1 to C10-aliphatic where substituted phenyl has one or more radicals selected from the group consisting of lower alkoxy, lower alkyl, trihalomethyl, and halo, or R is C1 to C20-aliphatic-O-, or R is unsubstituted or substituted phenyl-C1 to C10-aliphatic-O- where substituted phenyl has one or more radicals selected from the group consisting of lower alkoxy, lower alkyl, trihalomethyl, and halo; R1 is -(CH2)xCH=CHCORy, or -(CH2)xCH=CHCHO, where x is 0-2 and Ry is -OH or an ester thereof, or NH2 or a substituted amide derivative thereof; R2 is H, lower alkoxy, halo, -CN, -(CH2)nR4 where n is 0-5, lower alkyl, or CF3; R3 is H, lower alkoxy, halo, lower alkyl, CF3, -CN, -(CH2)nR4 where n is 0-5; R4 is tetrazol-5-yl or COR5; and R5 is lower alkoxy, CH3(CH2)0-6CO or phenyl(CH2)0-3CO...
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SYNTHESIS OF CARBAMOYLPYRIDONE HIV INTEGRASE INHIBITORS AND INTERMEDIATES (Thu, 17 Jun 2010)
A synthesis approach providing an early ring attachment via a bromination to compound 1-1 yielding compound II-I1, whereby a final product such as AA can be synthesized. In particular, the 2,4-difluorophenyl-containing sidechain is attached before creation of the additional ring Q.
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PEPTIDE DEFORMYLASE INHIBITORS (Thu, 06 Jun 2013)
The present invention relates to {2-(alkyl)-3-[2-(5-fluoro-4-pyrimidinyl)hydrazino]-3- oxopropyl}hydroxyformamide compounds of Formula (I): or pharmaceutically acceptable salts thereof, corresponding pharmaceutical compositions, processes for making and use of such compounds in the inhibition of bacterial peptide deformylase (PDF) activity and in treatment methods for bacterial infections.
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CRYSTALLIZATION OF OPTICAL ISOMERS OF LEUKOTRIENE ANTAGONISTS (Mon, 27 Jun 1994)
The specification is directed towards the following amine salts of leukotriene antagonists depicted by formula I. where: A is 1 and X is 1 or 2; R1 is C8 to C13 alkyl, C7 to C12 alkoxy, C7 to C12 alkylthio, C10 to C12 1-alkynyl, 10-undecynyloxy, 11-dodecynyl, phenyl-C4 to C10 alkyl, phenyl-C3 to C9 alkoxy, phenylthio-C3 to C9 alkyl with the phenyl unsubstituted or monosubstituted with bromo, chloro, trifluoromethyl, C1 to C4 alkoxy, methylthio or trifluoromethylthio, furyl-C4 to C10 alkyl, trifluoromethyl-C7 to C12 alkyl or cyclohexyl-C4 to C10 alkyl; q is 0, 1 or 2, with the proviso that R1 is not alkylthio or phenylthioalkyl when q is 1 or 2; Y is COR3, C(R4)H(CH2)mCOR3, or (CH2)0-1-C-tetrazolyl; R3 is 0-, amino, or C1 to C6 alkoxy, R4 is hydrogen, methyl, C1 to C4-alkoxy, fluoro or hydroxy; m is 0, 1, or 2; R is (CH2)nCOR6; n is 0 to 6; and R6 is 0-, amino, or C1 to C6-alkoxy; with the proviso that at least one of Y or R must have an R3 or R6 group respectively which is 0-. A process for selectively crystallising optical isomers of leukotriene antagonists is included...
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4 -substituted benzoxaborole compounds and uses thereof (Thu, 18 Aug 2016)
Substituted benzoxaboroles whose structure comprises Formula (III), wherein R3 is selected from –CH3, –CH2CH3, –CH2=CH2, –CH2CH2CH3, –CH(CH3)2, –CH2CH2=CH2, and cyclopropyl, R1 and R2 are each independently selected from H, -CH3, -CH2CH3, –CH2CH2CH3, and –CH(CH3)2; compositions containing such compounds, their use in therapy, including their use as anti-mycobacterial agents, for example in the treatment of a mycobacterial infection in a mammal, and methods for the preparation of such compounds, are provided.
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