cas 109-54-6, 3-Chloro-1-(N,N-dimethyl)propylamine

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Quinolinonyl Non-Diketo Acid Derivatives as Inhibitors of HIV-1 Ribonuclease H and Polymerase Functions of Reverse Transcriptase
Novel anti-HIV agents are still needed to overcome resistance issues, in particular inhibitors acting against novel viral targets. The ribonuclease H (RNase H) function of the reverse transcriptase (RT) represents a validated and promising target, and no inhibitor has reached the clinical pipeline yet. Here, we present rationally designed non-diketo acid selective RNase H inhibitors (RHIs) based on the quinolinone scaffold starting from former dual integrase (IN)/RNase H quinolinonyl diketo acids. Several derivatives were synthesized and tested against RNase H and viral replication and found active at micromolar concentrations. Docking studies within the RNase H catalytic site, coupled with site-directed mutagenesis, and Mg2+titration experiments demonstrated that our compounds coordinate the Mg2+cofactor and interact with amino acids of the RNase H domain that are highly conserved among na?ve and treatment-experienced patients. In general, the new inhibitors influenced also the polymerase activity of RT but were selective against RNase H vs the IN enzyme.
Messore, Antonella,Corona, Angela,Madia, Valentina Noemi,Saccoliti, Francesco,Tudino, Valeria,De Leo, Alessandro,Ialongo, Davide,Scipione, Luigi,De Vita, Daniela,Amendola, Giorgio,Novellino, Ettore,Cosconati, Sandro,Métifiot, Mathieu,Andreola, Marie-Line,Esposito, Francesca,Grandi, Nicole,Tramontano, Enzo,Costi, Roberta,Di Santo, Roberto
p. 8579 - 8598
(2021/06/30)

THIN-FILM FORMING RAW MATERIAL FOR USE IN ATOMIC LAYER DEPOSITION METHOD, THIN-FILM FORMING RAW MATERIAL, METHOD FOR PRODUCING THIN-FILM, AND COMPOUND
The present invention provides a thin-film forming raw material, which is used in an atomic layer deposition method, including a compound represented by the following general formula (1): where R1 to R4 each independently represent an alkyl group having 1 to 5 carbon atoms, and A1 represents an alkanediyl group having 1 to 5 carbon atoms.
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Paragraph 0105

(2021/11/05)

Discovery of novel TNNI3K inhibitor suppresses pyroptosis and apoptosis in murine myocardial infarction injury
Myocardial infarction (MI) injury is a highly lethal syndrome that has, until recently, suffered from a lack of clinically efficient targeted therapeutics. The cardiac troponin I interacting kinase (TNNI3K) exacerbates ischemia-reperfusion (IR) injury via oxidative stress, thereby promoting cardiomyocyte death. In this current study, we designed and synthesized 35 novel TNNI3K inhibitors with a pyrido[4,5]thieno[2,3-d] pyrimidine scaffold. In vitro results indicated that some of the inhibitors exhibited sub-micromolar TNNI3K inhibitory capacity and good kinase selectivity, as well as cytoprotective activity, in an oxygen-glucose deprivation (OGD) injury cardiomyocyte model. Furthermore, investigation of the mechanism of the representative derivative compound 6o suggested it suppresses pyroptosis and apoptosis in cardiomyocytes by interfering with p38MAPK activation, which was further confirmed in a murine myocardial infarction injury model. In vivo results indicate that compound 6o can markedly reduce myocardial infarction size and alleviate cardiac tissue damage in rats. In brief, our results provide the basis for further development of novel TNNI3K inhibitors for targeted MI therapy.
Bi, Zhiang,Chai, Jinlong,He, Gu,Pang, Haiying,Wang, Ning,Wang, Xiaoyun,Wu, Wenbin,Zhang, Yuehua
supporting information

(2020/04/27)

High-purity clomipamine hydrochloride and preparation method thereof
The invention relates to high-purity clomipamine hydrochloride and a preparation method thereof. Specifically, the preparation method comprises the following steps: reacting bromochloropropane with dimethylamine in the presence of alkali to obtain an intermediate I compound; adding 3-chlor-5-acetyl diphenyl imide and potassium hydroxide into toluene, and heating for reaction to obtain an intermediate II; adding potassium carbonate, potassium hydroxide into the intermediate II, and heating reactants, then adding a mixed solution of the intermediate I compound and methylbenzene, continuously heating to finish the reaction, then cooling the reaction solution, and adding water for extraction to obtain an organic layer containing clomipamine; concentrating the previous product under reduced pressure to obtain an oily substance, adding acetone, dropwise adding hydrochloric acid for acidification, crystallizing, centrifuging to obtain a crystal, and drying to obtain a clomipamine hydrochloride crude product; and adding the obtained clomipamine hydrochloride crude product and a solvent into a reaction kettle, heating for dissolving, adding medicinal carbon for reflux decolorization treatment, filtering for decarburization, cooling for crystallization, filtering for crystallization, and drying to obtain a clomipamine hydrochloride finished product. The method has the effects described in the specification.
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Paragraph 0080; 0089-0093; 0106-0109; 0118-0121; 0130-0133

(2020/11/23)

Preparation method of N-dimethylaminopropyl(meth)acrylamide
The invention discloses a preparation method of N-dimethylaminopropyl(meth)acrylamide. The preparation method comprises the following steps: firstly, carrying out alcohol derivatization on 3-dimethylamino-1-propanol; reacting the derivatization product with (meth)acrylamide in the presence of an organic solvent and an alkali to obtain the N-dimethylaminopropyl(meth)acrylamide. Compared with a conventional preparation method adopted in the market, the preparation method disclosed by the invention has the advantages that the reaction conditions are mild, the operation is simple and convenient, the control is easy, the preparation cost is relatively low, and the commercial value is relatively high.
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Paragraph 0046-0047

(2019/12/02)

Multifunctional cholinesterase inhibitors for Alzheimer's disease: Synthesis, biological evaluations, and docking studies of o/p-propoxyphenylsubstituted-1H-benzimidazole derivatives
This study indicates the synthesis, cholinesterase (ChE) inhibitory activity, and molecular modeling studies of 48 compounds as o- and p-(3-substitutedethoxyphenyl)-1H-benzimidazole derivatives. According to the ChE inhibitor activity results, generally, para series are more active against acetylcholinesterase (AChE) whereas ortho series are more active against butyrylcholinesterase (BuChE). The most active compounds against AChE and BuChE are compounds A12 and B14 with IC50 values of 0.14 and 0.22 μM, respectively. Additionally, the most active 16 compounds against AChE/BuChE were chosen to investigate the neuroprotective effects, and the results indicated that most of the compounds have free radical scavenging properties and show their effects by reducing free radical production; moreover, some of the compounds significantly increased the viability of SH-SY5Y cells exposed to H2O2. Overall, compounds A12 and B14 with potential AChE and BuChE inhibitory activities, high neuroprotection against H2O2-induced toxicity, free radical scavenging properties, and metal chelating abilities may be considered as lead molecules for the development of multi-target-directed ligands against Alzheimer's disease.
Sar?kaya, G?rkem,?oban, Güne?,Parlar, Sülünay,Tarikogullari, Ayse H.,Armagan, Güliz,Erdo?an, Mümin A.,Alptüzün, Vildan,Alpan, Ay?e S.
(2018/08/01)

HEPATITIS B CORE PROTEIN MODULATORS
The present disclosure provides, in part, compounds having allosteric effector properties against Hepatitis B virus Cp. Also provided herein are methods of treating viral infections, such as hepatitis B, comprising administering to a patient in need thereof a disclosed compound of formula:
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Page/Page column 116

(2018/04/13)

Preparation method of escitalopram oxalate impurities
The application of the invention provides a brand-new preparation method of (R)-4-(dimethylamino)-1-(1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-yl)-butyl-1-ketone to provide a basis for qualitative and quantitative analysis of impurity profiles in escitalopram oxalate finished products, thereby having a significant role in quality control of escitalopram oxalate and being capable of promoting the safe use of depressive patients.
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Paragraph 0021

(2017/08/29)

Preparation method of citalopram intermediate
The invention provides a preparation method of a citalopram intermediate, and belongs to the technical field of pharmaceuticals. In the method, 2-methyltetrahydrofuran is taken as a reaction solvent. Under the protection of nitrogen, a 4-fluorophenylmagnesium bromide solution Grignard reagent, 5-cyanophthalein and a N,N-dimethylpropyl magnesium chloride Grignard reagent are taken as raw materials. A reaction is carried out to synthesize 4-(4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrilehydrobromide. The method is characterized by high yield and high purity, and is suitable for industrial production.
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Paragraph 0128; 0129; 0130; 0131; 0132

(2016/12/01)

Synthesis of scutellarein derivatives to increase biological activity and water solubility
In order to improve the biological activity and water solubility of scutellarin (1), some derivatives of its main metabolite (scutellarein) were designed and synthesized. All the compounds were tested for their thrombin inhibition activity through the analyzation of thrombin time (TT), activated partial thromboplastin time (APTT), prothrombin time (PT) and fibrinogen (FIB). Their antioxidant activities were assessed by measuring their scavenging capacities toward 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) and the ability to protect PC12 cells against H2O2-induced cytotoxicity, their water solubility were also assessed by ultraviolet (UV) spectrophotometer. The results showed that compound 8b demonstrated stronger anticoagulant and antioxidant activity, better water solubility compared with scutellarein (2), which warrants it as a promising agent for the treatment of ischemic cerebrovascular disease.
Shi, Zhi-Hao,Li, Nian-Guang,Shi, Qian-Ping,Zhang, Wei,Dong, Ze-Xi,Tang, Yu-Ping,Zhang, Peng-Xuan,Gu, Ting,Wu, Wen-Yu,Fang, Fang,Xin-Xue,Li, He-Min,Yang, Jian-Ping,Duan, Jin-Ao
p. 6875 - 6884
(2015/11/11)

Dye/Clay intercalated nanopigments using commercially available non-ionic dye
Two non-ionic azo dyes: solvent yellow 14 (SY14) and solvent red 24 (SR24), and one non-ionic disperse dye: dispersed red 60 (DR60) were chemically modified into their respective cationic species, which were then subsequently ion-exchanged with Na+-montmorillonite in an acidic medium. The dye-intercalated montmorillonite was then centrifuged, dried and milled to prepare the pigment particles. X-ray diffraction studies on the pigments showed an increase in the basal spacing in the clay layers for the SY14 and DR60 based pigments NP14 and NP60 respectively, confirming intercalation of the dyes within the clay layers giving rise to a nano-structured system. The XRD pattern of the SR24 based pigment NP24 showed a diffused shoulder with a truncated peak, suggesting the possibility of a delaminated structure after adsorption of the dye. Due to the nano-structured morphologies, these pigments were classified as nanopigments. Thermogravimetric analysis showed different thermal stabilities for different nanopigments compared to the respective original dyes: an improvement in case of NP14, no change for NP24, and an apparent deterioration for NP60. The nanopigments were subsequently mixed with polypropylene to produce coloured specimens. Bleeding tests on these coloured specimens showed a reduction in leaching in turpentine.
Raha, Sumanta,Quazi, Nurul,Ivanov, Ivan,Bhattacharya, Sati
experimental part
p. 1512 - 1518
(2012/03/27)

PREPARATION OF ESCITALOPRAM, ITS SALTS AND INTERMEDIATES
The present patent application relates to an improved process for the preparation of escitalopram, its salts and intermediates. It also relates to a novel crystalline form S of citalopram diol intermediate, process for preparation and its use in the preparation of citalopram, escitalopram and their salts.
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Page/Page column 16-17

(2010/04/03)

BENZOCYCLOHEPTANE AND BENZOXEPINE DERIVATIVES
The present invention relates to a compound of formula (I), including any stereochemically isomeric form thereof, wherein the substituents are as defined in the specification and the claims; a N-oxide thereof, a pharmaceutically acceptable salt thereof or a solvate thereof; provided that the compound is other than formula (B) or a pharmaceutically acceptable salt thereof. The claimed compounds are useful for the treatment of a disease, the treatment of which is affected, mediated or facilitated by activating the GHS1A-r receptor. The invention also relates to pharmaceutical compositions thereof and processes for the preparation thereof.
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Page/Page column 42

(2009/12/05)

AMINOALKOXY ARYL SULFONAMIDE COMPOUNDS AND THEIR USE AS 5-HT6 LIGANDS
The present invention relates to novel aminoalkoxy arylsulfonamide compounds of the formula (I), their derivatives, their stereoisomers, their pharmaceutically acceptable salts and pharmaceutically acceptable compositions containing them. The present invention also relates to a process for the preparation of above said novel compounds, their derivatives, their stereoisomers, their pharmaceutically acceptable salts and pharmaceutically acceptable compositions containing them. These compounds are useful in the treatment of various disorders that are related to 5-HT6 receptor functions. Specifically, the compounds of this invention are also useful in the treatment of various CNS disorders, hematological disorders, eating disorders, diseases associated with pain, respiratory diseases, genito-urological disorders, cardiovascular diseases and cancer.
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Page/Page column 30

(2009/01/20)

METHOD FOR THE PREPARATION OF ESCITALOPRAM
The invention relates to novel intermediates and the use thereof in a novel method for the preparation of escitalopram.
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Page/Page column 20

(2008/06/13)

IMPROVED PROCESS FOR THE MANUFACTURE OF CITALOPRAM HYDROBROMIDE
The present invention describes an improved process for the preparation of extremely pure 1-(4'-Fluorophenyl)-1-(3-dimethylaminopropyl)-5-phthalanecarbonitrile and its bromide salt (citalopram hydrobromide), which is a well known antidepressant. Other aspect of the invention are isolation of crystalline (4-Bromo-2-hydroxymethyl)phenyl-(4-fluorophenyl)-3-(dimethylaminopropyl)methanol (Bromodiol) and conversion of desmethylcitalopram which is formed during the cyanide exchange reaction, to Citalopram by heating with a mixture of formaldhyde and formic acid in chloroform. The resulting citalopram is conventionally purified using extraction methodology.
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Page/Page column 9-10

(2008/06/13)

Method of manufacturing citalopram
The present invention provides, inter alia, a novel process for the preparation of Citalopram, a known antidepressant.
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Page/Page column 24-25

(2010/02/11)

Process for the preparation of citalopram
Preparation of citalopram comprises the steps of: (a) converting the compound of Formula (I) to a compound of Formula (II), wherein R in Formula (I) represents a C2 to C5 alkylene group which may be substituted or unsubstituted, and R1 in the compounds of Formula (II) represents a carboxylic acid group or a salt or an ester thereof; and (b) converting the compound of Formula (II) to form citalopram or a pharmaceutically acceptable salt thereof, or a direct conversion of the compound of Formula (I) to citalopram
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Page 10

(2010/02/05)

A NOVEL PROCESS FOR PREPARATION OF INDOLE DERIVATIVES
A novel process of preparation of a compound of 3-(2-Dimethylamino)-N-methyl-lH-indole-5-methane sulfonamide, which comprises of a reaction 4-hydrazino-N-methyl benzene methane sulfonamide with 4-dimethyl amino butyraldehyde diethyl acetal in a chlorinated solvent in the presence of ethyl poly phosphate and conversion of the crude product to a product of 3-(2-Dimethylamino)-N-methyl-lH-indole-5-methane sulfonamide succinate of extra high purity and colour.
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Page 9-10

(2010/02/09)

PROCESS AND INTERMEDIATES FOR PREPARING ESCITALOPRAM
The antidepressant drug Escitalopram is prepared from 5-bromophthalide via the diol intermediate (4-bromo-2-(hydroxymethyl)phenyl)-(4-fluorophenyl)methanol. The racemic diol intermediate is converted to an enantiomerically enriched form by first converting the diol to a monoester intermediate and then reacting the monoester intermediate with an optically active acid, most preferably (+)-di-p-toluoyl tartaric acid, to form a salt. The salt is then crystallized to recover an enantiomerically enriched, crystalline form thereof. The monoester intermediate is preferably formed by reacting the racemic diol intermediate with an acid or a reactive acid derivative which, in a particularly preferred embodiment, is acetic anhydride.
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Page/Page column 9

(2008/06/13)

AN IMPROVED PROCESS FOR THE PREPARATION OF 4-(N, N-DISUBSTITUTEDAMINO) BUTYRALDEHYDE ACETALS
The invention disclosed in this application relates to an improved process for the preparation of compounds of formula (I): R1R2NCH2CH2CH2CH(OR3)2; wherein, R1 = R2 = C1-C16 alkyl; C3-C7 cycloalkyl; R1 = C1-C16 alkyl; R2 = C3-C7 cycloalkyl; NR1R2 = pyrrolidino, piperidino, morpholino, thiomorpholino, R1 = C1-C6 alkyl; R2 = ArCH2; Ar =4-R4-C6H4-, R4 = MeO, EtO, Me, Et, NMe2, NEt2, SMe, SEt, etc; R3=C1-C6 alkyl; C3-C7 cycloalkyl which comprises: (i) Reacting 3-(N, N-disubstitutedamino)propyl halide of formula (XXI): R1R2NCH2CH2CH2X; wherein, R1, R2 = as defined above, X = C1 or Br, with magnesium in the presence of a solvent to get the Grrgnard reagent 3-(N, N-disubstitutedamino)-propylmagnesium halide; (ii) Reacting the resulting 3-(N, N-disubstitutedamino) propylmagnesium halide (Grignard reagent) with the trisubstituted orthoformate of formula (XVII): HC(OR5)(OR3)2; wherein, R3 and R5 is same or different and represent C1 to C6 alkyl, C3 to C7 cycloalkyl OR R3 is as defined above and R5 represents phenyl radical; (iii) Filtering off the resultant reaction mixture and distilling the filtrate to isolate the compound of the formula (I). These substituted butyraldehyde derivatives of the formula (I) are very important building blocks for the synthesis of various tryptamine derivatives. In particular 4-(N, N-dimethylamino)butyraldehyde dimethyl or diethyl acetals are crucial intermediates for the synthesis of commercially available anti-migraine drugs, like sumatriptan, zolmitriptan, and rizatriptan.
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Page 10-15; 19

(2010/02/04)

PRODUCTION METHOD OF CITALOPRAM, INTERMMEDIATE THEREFOR AND PRODUCTION METHOD OF THE INTERMEDIATE
Citalopram can be industrially and economically produced and at a high yield by reacting a compound of the following formula [VI] with 3-(dimethylamino)propyl chloride in the presence of at least one of N,N,N′,N′-tetramethylethylenediamine and 1,3-dimethyl-2-imidazolidinone and a condensing agent. The compound of the following formula [III], which is a key compound for the production of citalopram, can be easily produced by subjecting the compound of the following formula [II] to reduction and cyclization. 1
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(2008/06/13)

Thiadiazinones
The present invention relates to thiadiazinones of the formula I STR1 having a phosphodiesterase-inhibiting action and which are suitable for combating cardiovascular and asthmatic disorders.
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(2008/06/13)

5-SUBSTITUTED AND 5,7-DISUBSTITUTED 5,7-DIHYDRODIBENZOTHIEPINS AND THE CORRESPONDING S-OXYGENATED COMPOUNDS: ALKYLAMINES, CARBOXYLIC ACIDS, AND CARBOXAMIDES; SYNTHESIS AND PHARMACOLOGICAL SCREENING
Reaction of 5,7-dihydrodibenzothiepin with n-butyllithium resulted in the partial sulfur extrusion and in the formation of the 9,10-dihydrophenanthrene-9-thiolate anion (B).Its further transformations (by hydrolysis, aminoalkylation and spontaneous dehydrogenation) led to phenanthrene-9-thiol (IX), the corresponding disulfide X, and the S-(2-dimethylaminoethyl) derivatives XI and XIV.Reactions of 5-chloro-5,7-dihydrodibenzothiepin (II) with the corresponding Grignard reagents were only a poor source of the amines III and IV.Reaction of the sulfoxide XVIII with n-butyllithium or with sodium hydride and the following treatment with 2-dimethylaminoethyl chloride gave the amine XIX in a low yield.Only the sulfone X was found more useful for preparing the 5- and 5,7-substituted derivatives.Treatment with n-butyllithium and following carbonation afforded mixtures of the monocarboxylic acid XXI and dicarboxylic acid XXVIII.Via acid chlorides they were transformed to the methylamides XXII and XXIX and to the dimethylamides XXIII and XXX.The amide XXIII was reduced to the 5-(dimethylaminomethyl) compound XXV.Lithiation of the sulfone XX or treatment with sodium hydride and the following action of 2-dimethylaminoethyl chloride and 3-dimethylaminopropyl chloride gave the amines XXVI, XXVII, and XXXI.Only the phenanthrene derivatives XI and XIV, and the amino sulfone XXVII showed clear indications of thymoleptic activity as potential antidepressants.
Sindelar, Karel,Holubek, Jiri,Ryska, Miroslav,Koruna, Ivan,Protiva, Miroslav
p. 2848 - 2868
(2007/10/02)

Introduction of Pharmacorphoric Groups into Polycyclis Systems. Part 3. Amine Derivatives of Adamantane and Diaza-adamantane
Methods for introducing various pharmacophoric amine-containing substituents into the adamantane system have been investigated.These include β- and α-aminoalkyloxyimino, β-aminoalkylidine, β-hydroxyethylamino, and β-phenylethylamino.Aminoalkoxyimines were prepared by alkylation of the anion of adamantanone oxime with the corresponding aminoalkyl chloride, and a 2-aminoethylidene derivative was prepared by Witting reaction of 2-dimethylaminoethyltriphenylphosphonium bromide with adamantanone.The reaction of 6-hydroxy-7-methyl-6-phenyladamantane-2,4-dione with aqueous sodium cyanide has been shown to be both regio- and stereo-selective, only the C-2 carbonyl group reacting from the most hindered direction.This is possibly due to stabilisation of the cyanohydrin by hydrogen bonding between the hydroxy and C-4 carbonyl groups.When trimethyl cyanide was used in place of sodium cyanide, the reaction remained regioselective but, in the absence of hydrogen bond stabilisation, the stereoselectivity was lost and two trimethylsilyloxy cyanides were isolated, epimeric at C-2.The stereochemistry of one epimer has been determined by X-ray crystallography, details of which are reported here.Hydrogenation of the trimethylsilyloxy cyanides then gave the corresponding β-hydroxyamine, isolated as the hydrochloride.Finally 5,7-diphenyl-1,3-diaza-adamantan-6-one was prepared by a literature method and converted, with difficulty, into the oxime which was reduced by RedAl to the corresponding amine.
Hickmott, Peter W.,Wood, Simon,Murray-Rust, Peter
p. 2033 - 2038
(2007/10/02)

Ethereal monosubstitutions of monosaccharide derivatives
The invention provides a novel therapeutic composition comprising a pharmaceutically acceptable carrier containing a therapeutically effective amount of an ethereal monosubstitution of a monosaccharide derivative having the general formula S--O--Y, wherein S is the residue of the monosaccharide derivative selected from the group consisting of pentoses, hexoses and heptoses as single or polysubstituted acetals, ketals or esters and Y is selected from the group consisting of cyclic monovalent nitrogen-containing organic radicals and residua and monovalent organic radicals and residua having the general formula STR1 wherein R1 is a divalent organic radical having a linear carbon chain length of about 1-7 carbon atoms and R2 and R3 are selected from the group consisting of --H, --OH, --SH, halogen and monovalent organic radicals and residua having a linear carbon chain length of about 1-7 carbon atoms. The invention also provides certain novel ethereal monosubstitutions of monosaccharide derivatives, of which 3-O-3'-(N',N'-dimethylamino-n-propyl)-1,2-O-isopropylidene-D-glucofuranose is an example. The novel monosaccharide derivatives show striking antiviral activity or other therapeutically valuable properties and are useful as active ingredients in the above therapeutic composition. The invention further provides a method of therapeutically treating warm-blooded animals with the aforementioned therapeutic composition and novel monosubstituted monosaccharide derivatives.
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(2008/06/13)

Sulfonyl benzofurans and benzothiophenes having coronary vasodilator activity
The compounds are sulfonyl benzofurans and benzothiophenes having pharmacological activity, in particular, coronary vasodilator activity useful for the treatment of angina pectoris.
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(2008/06/13)

Preparation of ethers of monosaccharides
Ethereally substituted monosaccharides are prepared from certain selectively derivatized monosaccharides. In practicing the method: 1. a monosaccharide derivative having the general formula A1 -O-H, wherein O is oxygen, H is hydrogen and A1 is the residue of a monosaccharide selected from the group consisting of pentoses, hexoses and heptoses which has been derivatized with at least one substance selected from the group consisting of (1-a) at least one aliphatic alcohol containing 1-18 carbon atoms to produce an hydrolyzable acetal group at the site of at least one available hydroxyl residue, (1-b) at least one aldehyde containing 1-18 carbon atoms to produce at least one hydrolyzable acetal group at the site of at least one available hydroxyl residue, (1-c) at least one ketone containing 1-18 carbon atoms to produce at least one hydrolyzable ketal group at the site of at least one available hydroxyl residue, and (1-d) at least one organic acid residue containing 1-18 carbon atoms to produce an hydrolyzable ester group at the site of at least one available hydroxyl residue; is reacted with 2. an organic halide having the general formula Y - X, wherein X is selected from the group consisting of chlorine, bromine and iodine and Y is selected from the group consisting of (2-a) cyclic monovalent nitrogen containing organic radicals and residua, and (2-b) monovalent organic radicals and residue having the general formula -R1 B wherein B is selected from the group consisting of STR1 --O--R4 and --S--R4, R1 is a divalent organic radical having a linear carbon chain length of about 1-7 carbon atoms, R2 and R3 are selected from the group consisting of --H,--OH, --SH, halogen and monovalent organic radicals and residua having a linear carbon chain length of about 1-7 carbon atoms, R4 is selected from the group consisting of --H and monovalent organic radicals and residua having a linear carbon chain length of about 1-7 carbon atoms, N is nitrogen, O is oxygen, S is sulfur and H is hydrogen; To produce an ethereally substituted monosaccharide derivative having the general formula A-O-Y wherein A, Y and O are as above defined. The monosaccharide derivative (1) and the organic halide (2) are reacted at an elevated reaction temperature while dissolved in a substantially anhydrous organic solvent in the presence of a solid substantially anhydrous strong inorganic base of a metal selected from the group consisting of the alkali metals and the alkaline earth metals. The resultant ethereally substituted monosaccharides may be partially or fully hydrolyzed in an aqueous acidic medium. In one preferred variant, 1,2:5,6-di-O-isopropylidene 3-O-3'-(N',N'-dimethylamino-n-propyl)-D-glucofuranose is prepared and, when desired, thereafter partially or fully hydrolyzed to produce 1,2-O-isopropylidene-3-O-3'-(N',N'-dimethylamino-n-propyl)-D-glucofuranose or 3-O-3'-(N'-N'-dimethylamino-n-propyl-D-glucose in the free amine and/or salt forms. The method is capable of preparing the ethereally substituted monosaccharides in high yield and purity with a minimum of side products. The resultant compounds exhibit striking antiviral activity and/or have other therapeutically valuable properties and are useful in the treatment of warm-blooded animals.
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(2008/06/13)

Novel ethereally monosubstituted monosaccharides
The invention provides a novel therapeutic composition comprising a pharmaceutically acceptable carrier containing a therapeutically effective amount of an ethereally monosubstituted monosaccharide having the general formula S-O-Y, wherein S is the residue of a monosaccharide selected from the group consisting of pentoses, hexoses and heptoses and Y is selected from the group consisting of cyclic monovalent nitrogen containing organic radicals and residua and monovalent organic radicals and residua having the general formula EQU1 wherein R1 is a divalent organic radical having a linear carbon chain length of about 1-7 carbon atoms and R2 and R3 are selected from the group consisting of --H, --OH, --SH, halogen and monovalent organic radicals and residua having a linear carbon chain length of about 1-7 carbon atoms. The invention also provides certain novel ethereally monosubstituted monosaccharides, of which 3-O-3'-(N',N'-dimethylamino-n-propyl)-D-glucose is an example. The novel monosaccharides show striking antiviral activity or other therapeutically valuable properties and are useful as an active ingredient in the above therapeutic composition. The invention further provides a method of therapeutically treating warm blooded animals with the aforementioned therapeutic composition and novel monosubstituted monosaccharides.
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(2008/06/13)

Novel ethereal monosubstitutions of monosaccharide derivatives
The invention provides a novel therapeutic composition comprising a pharmaceutically acceptable carrier containing a therapeutically effective amount of an ethereal monosubstitution of a monosaccharide derivative having the general formula S--O--Y, wherein S is the residue of the monosaccharide derivative selected from the group consisting of pentoses, hexoses and heptoses as single or polysubstituted acetals, ketals or esters and Y is selected from the group consisting of cyclic monovalent nitrogen-containing organic radicals and residua and monovalent organic radicals and residua having the general formula EQU1 wherein R1 is a divalent organic radical having a linear carbon chain length of about 1-7 carbon atoms and R2 and R3 are selected from the group consisting of --H, --OH, --SH, halogen and monovalent organic radicals and residua having a linear carbon chain length of about 1-7 carbon atoms. The invention also provides certain novel ethereal monosubstitutions of monosaccharide derivatives, of which 3-O-3'-(N',N'-dimethylamino-n-propyl)-1,2-O-isopropylidene-D-glucofuranose is an example. The novel monosaccharide derivatives show striking antiviral activity or other therapeutically valuable properties and are useful as active ingredients in the above therapeutic composition. The invention further provides a method of therapeutically treating warm-blooded animals with the aforementioned therapeutic composition and novel monosubstituted monosaccharide derivatives.
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(2008/06/13)

Substituted benzofurans and benzothiophenes
The compounds of this invention are substituted benzofurans and benzothiophenes having pharmacological activity. In particular, these compounds have coronary vasodilator activity and are useful in the treatment angina pectoris.
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(2008/06/13)