- Synthesis of a 1,8-napththyridin-5-one derivative via an intramolecular 1,3-dipolar cycloaddition reaction
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Synthesis of a 1,8-naphthyridin-5-one derivative [(5,6,7,8-tetrahydro-(3-chloro-6-hydroxymethyl-8-methyl)-1,8-naphthyri din-5-one (9)] is described starting from 2-chloronicotinic acid using an intramolecular 1,3-dipolar cycloaddition reaction as the key step.
- Read,Ray
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Read Online
- Method for preparing aldehyde and acid by electrochemical dehydrochlorination of polychloromethylpyridine derivatives
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The invention discloses a method for preparing aldehyde and an acid by electrochemical dechlorination of a polychloromethylpyridine derivative, the method comprises the following steps: dissolving thepolychloromethylpyridine derivative in an acetic acid and acetate- containing buffer solution to obtain an electrolytic reaction solution; taking the electrolytic reaction solution as a cathode liquid, performing electrolytic reduction dechlorination reaction at a cathode, and hydrolyzing in the solution to obtain a polychlorinated pyridylaldehyde or acid derivative. The polychloromethylpyridinederivative is shown in formula (I), and the product polychlorinated pyridylaldehyde or acid derivative is shown in formula (II): in the formula (I), m is 0, 1, 2, 3 or 4, n is 0 or 1, and R' is an easy-to-oxidize or easy-to-hydrolyze substituent. The m and the R' in the formula (II) are same as that in the formula (I), R is H or OH, no waste acid is generated in the preparation process, the easy-to-oxidize or easy-to-hydrolyze substituent contained in the polychloromethylpyridine derivative and carbon-chlorine bonds on pyridine rings are not affected, and the recovery conversion rate is high.
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Paragraph 0035-0037; 0057-0064
(2020/08/27)
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- FUSED BICYLIC PYRIDINE COMPOUNDS AND THEIR USE AS AMPA RECEPTOR MODULATORS
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Provided herein are compounds of Formula (I), and pharmaceutically acceptable salts, N-oxides, or solvates thereof, Also provided herein are pharmaceutical compositions comprising compounds of Formula (I) and methods of using compounds of Formula (I).
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Paragraph 0363
(2018/05/03)
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- A 2 - chloro - 3 - pyridine formaldehyde synthetic method (by machine translation)
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The invention discloses a 2 - chloro - 3 - pyridyl aldehyde synthesis method, the method to 2 - chloro - 3 - methyl pyridine as raw materials, passes through chlorine chlorinated, ester hydrolysis, oxidation three-step to obtain 2 - chloro - 3 - pyridine formaldehyde product. The method of the invention mild reaction conditions, high yield, low cost, product purity up to 98% or more, and has a good industrial application prospect. (by machine translation)
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- PYRIMIDINE AND TRIAZINE DERIVATIVES AND THEIR USE AS AXL INHIBITORS
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Compounds of the general formula(I): (I) processes for the preparation of these compounds, compositions containing these compounds, and the uses of these compounds.
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Page/Page column 51
(2016/07/05)
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- Synthesis and pharmacological evaluation of N-benzyl substituted 4-bromo-2,5-dimethoxyphenethylamines as 5-HT2A/2C partial agonists
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N-Benzyl substitution of phenethylamine 5-HT2A receptor agonists has dramatic effects on binding affinity, receptor selectivity and agonist activity. In this paper we examine how affinity for the 5-HT2A/2C receptors are influenced by N-benzyl substitution of 4-bromo-2,5-dimethoxyphenethylamine derivatives. Special attention is given to the 2′ and 3′-position of the N-benzyl as such compounds are known to be very potent. We found that substitutions in these positions are generally well tolerated. The 2′-position was further examined using a range of substituents to probe the hydrogen bonding requirements for optimal affinity and selectivity, and it was found that small changes in the ligands in this area had a profound effect on their affinities. Furthermore, two ligands that lack a 2′-benzyl substituent were also found to have high affinity contradicting previous held notions. Several high-affinity ligands were identified and assayed for functional activity at the 5-HT2A and 5-HT2C receptor, and they were generally found to be less efficacious agonists than previously reported N-benzyl phenethylamines.
- Hansen, Martin,Jacobsen, Stine Engesgaard,Plunkett, Shane,Liebscher, Gudrun Eckhard,McCorvy, John D.,Br?uner-Osborne, Hans,Kristensen, Jesper Langgaard
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supporting information
p. 3933 - 3937
(2015/01/30)
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- Novel aromatic fluoroolefins via fluoro-Julia-Kocienski olefination
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Fluoroolefins, which play an increasingly important role as peptide mimics in pharmaceuticals and as crop protection agents, are generated using a fluoro-Julia-Kocienski olefination. Their preparation can easily be accomplished using a Mitsunobu reaction and subsequent oxidation to generate the required benzothiazolyl sulfones. The key step of this process was the electrophilic -fluorination of the sulfone with N-fluorobenzenesulfonimide. The last stage of the successful synthesis of the fluoroolefins was the modified Julia-Kocienski olefination under basic conditions. Further functionalization was followed with the application of a Suzuki reaction. Georg Thieme Verlag Stuttgart.
- Allendoerfer, Nadine,Es-Sayed, Mazen,Nieger, Martin,Braese, Stefan
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scheme or table
p. 3439 - 3448
(2010/12/19)
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- Efficient route to medium-ring benzo- and azabenzo-lactones
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The synthesis of precursors of medium-ring benzo- and azabenzo-lactones is performed efficiently from simple ortho-halo aryl and heteroaryl aldehydes. Copyright Taylor & Francis Group, LLC.
- Metay, Estelle,Leonel, Eric,Nedelec, Jean-Yves
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p. 889 - 904
(2008/09/17)
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- A novel class of cycloalkano[b]pyridines as potent and orally active opioid receptor-like 1 antagonists with minimal binding affinity to the hERG K + channel
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A series of compounds based on 7-{[4-(2-methylphenyl)piperidin-1-yl]methyl} -6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-9-ol ((-)-8b), a potent and selective opioid receptor-like 1 (ORL1) antagonist, was prepared and evaluated using structure-activity relationship studies with the aim of removing its affinity to human ether-a-go-go related gene (hERG) K+ channel. From these studies, 101 was identified as an optimized structure with respect to ORL1 antagonist activity, and affinity to the hERG K+channel. Furthermore, 101 showed good in vivo antagonism with a wide therapeutic index in regards to adverse cardiovascular effects.
- Yoshizumi, Takashi,Takahashi, Hirobumi,Miyazoe, Hiroshi,Sugimoto, Yuichi,Tsujita, Tomohiro,Kato, Tetsuya,Ito, Hirokatsu,Kawamoto, Hiroshi,Hirayama, Mioko,Ichikawa, Daisuke,Azuma-Kanoh, Tomoko,Ozaki, Satoshi,Shibata, Yoshihiro,Tani, Takeshi,Chiba, Masato,Ishii, Yasuyuki,Okuda, Shoki,Tadano, Kiyoshi,Fukuroda, Takahiro,Okamoto, Osamu,Ohta, Hisashi
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supporting information; experimental part
p. 4021 - 4029
(2009/05/26)
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- Method of Treating Pathological Blushing
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A method of treating pathological blushing is disclosed wherein the patient is administered a DP receptor antagonist. Compositions containing DP antagonists are also included.
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Page/Page column 16
(2010/11/29)
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- METHOD OF TREATING ATHEROSCLEROSIS, DYSLIPIDEMIAS AND RELATED CONDITIONS
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A method of treating atherosclerosis is disclosed wherein nicotinic acid or another nicotinic acid receptor agonist is administered to the patient in combination with a DP receptor antagonist. The DP receptor antagonist is administered to reduce, prevent
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Page/Page column 49
(2008/06/13)
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- NIACIN RECEPTOR AGONISTS, COMPOSITIONS CONTAINING SUCH COMPOUNDS AND METHODS OF TREATMENT
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The present invention encompasses compounds of Formula I: as well as pharmaceutically acceptable salts and hydrates thereof, that are useful for treating dyslipidemias. Pharmaceutical compositions and methods of use are also included.
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Page/Page column 64-65
(2008/06/13)
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- METHOD OF TREATING ATHEROSCLEROSIS, DYSLIPIDEMIAS AND RELATED CONDITIONS
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A method of treating atherosclerosis, dyslipidemia and related conditions is disclosed wherein a compound of formula I: or a pharmaceutically acceptable salt or solvate thereof is administered to the patient in combination with a DP receptor antagonist. T
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Page/Page column 32
(2010/10/20)
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- NIACIN RECEPTOR AGONISTS, COMPOSITIONS CONTAINING SUCH COMPOUNDS AND METHODS OF TREATMENT
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The present invention encompasses compounds of Formula (I); as well as pharmaceutically acceptable salts and hydrates thereof, that are useful for treating dyslipidemias. Pharmaceutical compositions and methods of use are also included.
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Page/Page column 81
(2010/11/08)
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- Pyridine metallations in the synthesis of triazole based NK-1 antagonists
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Regioselective pyridine metallation chemistry was used to produce N-(3-chloropyridin-4-ylmethyl)-N-methyl-1-(3,5-bis-trifluoromethylbenzyl)-5-phenyl-1H-[1,2,3]triazole-4-carboxamide (9a) and [1-(3,5-bis-trifluoromethyl-benzyl)-5-morpholin-4-yl-1H-[1,2,3]t
- Jeff Thrasher,Hembre, Erik J.,Gardinier, Kevin M.,Savin, Kenneth A.,Hong, Jian Eric,Jungheim, Louis N.
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p. 543 - 547
(2007/10/03)
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- NIACIN RECEPTOR AGONISTS, COMPOSITIONS CONTAINING SUCH COMPOUNDS AND METHODS OF TREATMENT
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The present invention relates to niacin receptor agonists of formula: (I); as well as pharmaceutically acceptable salts and solvates. The compounds are useful for treating dyslipidemias, and in particular, reducing serum LDL, VLDL and triglycerides, and raising HDL levels. Pharmaceutical compositions and methods of treatment are also included.
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Page/Page column 103-104
(2010/11/30)
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- HETEROARYLSULFONYL STILBENES AS 5-HT2A ANTAGONISTS
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Compounds of formula I: are potent and selective antagonists of the 5-HT2A receptor, and hence are useful in treatment of various 10 CNS disorders.
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Page/Page column 26
(2008/06/13)
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- CYCLOALKANOPYRIDINE DERIVATIVE
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Provided are cycloalkanopyridine derivatives of formula [I]: [wherein the symbols are the same as those stated in the description]. The compounds act as a nociceptin receptor antagonist, and are useful as medicines for diseases associated with a nociceptin receptor, for example, as a reliever against tolerance to a narcotic analgesic; a reliever against dependence on or addiction to a narcotic analgesic; an analgesic enhancer; an antiobesitic or appetite suppressor; a treating or prophylactic agent for cognitive impairment and dementia/amnesia; an agent for treating developmental cognitive abnormality; a remedy for schizophrenia; an agent for treating neurodegenerative diseases; an anti-depressant or treating agent for affective disorder; a treating or prophylactic agent for diabetes insipidus; a treating or prophylactic agent for polyuria; or a remedy for hypotension.
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Page/Page column 47
(2010/11/24)
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- Synthesis of aromatic analogs of 8(S)-HETE and their biological evaluation as activators of the PPAR nuclear receptors
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A new family of 8-HETE analogs has been synthesized as dual PPAR α and γ agonists. A versatile strategy has been developed to allow modulations not only around the aromatic core but also on the side chains of these analogs. The affinity of these compounds
- Caijo, Frederic,Mosset, Paul,Gree, Rene,Audinot-Bouchez, Valerie,Boutin, Jean,Renard, Pierre,Caignard, Daniel-Henri,Dacquet, Catherine
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p. 2181 - 2196
(2007/10/03)
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- TACHYKININ RECEPTOR ANTAGONISTS
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The present invention relates to selective NK-1 receptor antagonists of Formula (I) or a pharmaceutically acceptable salt thereof, for the treatment of disorders associated with an excess of tachykinins.
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- Synthesis of new carbo- and heterocyclic analogues of 8-HETE and evaluation of their activity towards the PPARs
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A new class of dual PPARs α and γ agonists was developed. These compounds are structural analogues of the arachidonic acid metabolite, the 8-(S)-HETE. A versatile strategy has been introduced to prepare the target molecules having different carbo- and het
- Caijo, Frederic,Mosset, Paul,Gree, Rene,Audinot-Bouchez, Valerie,Boutin, Jean,Renard, Pierre,Caignard, Daniel-Henri,Dacquet, Catherine
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p. 4421 - 4426
(2007/10/03)
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- PYRIDOPYRROLIZINE AND PYRIDOINDOLIZINE DERIVATIVES
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Pyridopyrrolizine and pyridoindolizine derivatives are prostaglandin receptor antagonists useful for the treatment of prostaglandin-mediated diseases such as allergic rhinitis, nasal congestion and asthma.
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- Method of treating atherosclerosis, dyslipidemias and related conditions
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A method of treating atherosclerosis is disclosed wherein nicotinic acid or another nicotinic acid receptor agonist is administered to the patient in combination with a DP receptor antagonist. The DP receptor antagonist is administered to reduce, prevent or eliminate flushing that may otherwise occur.
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- Quinuclidines-substituted-multi-cyclic-heteroaryls for the treatment of disease
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The invention provides compounds of Formula I: 1where in W is 2These compounds may be in the form of pharmaceutical salts or compositions, racemic mixtures, or pure enantiomers thereof. The compounds of Formula I are useful to treat diseases or conditions in which α7 is known to be involved.
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- Asymmetric synthesis of a selective endothelin a receptor antagonist
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An asymmetric synthesis of a selective endothelin A receptor antagonist 1b is described. Asymmetric conjugate addition of aryllithium derived from 18 to the chiral oxazoline 17 followed by hydrolysis afforded 15 in 96% ee via purification as (S)-(-)-1-phe
- Kato, Yoshiaki,Niiyama, Kenji,Jona, Hideki,Okada, Shigemitsu,Akao, Atsushi,Hiraga, Shouichi,Tsuchiya, Yoshimi,Tomimoto, Koji,Mase, Toshiaki
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p. 1066 - 1072
(2007/10/03)
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- Synthesis and antifungal activities of R-102557 and related dioxane- triazole derivatives
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Novel triazole compounds with a dioxane ring were synthesized. Condensation of the diol precursor 10 with various aromatic aldehydes 11 - 13 under acidic conditions afforded a series of dioxane-triazole compounds 14 - 16. The antifungal activities of the compounds 14 - 16 were evaluated in vivo in mice infection models against Candida and Aspergillus species. High activities were seen for the derivatives with one or two double bond(s) and an aromatic ring substituted with an electron-withdrawing group in the side chain. Among the derivatives, R-102557 (16R: Ar=4-(2,2,3,3- tetrafluoropropoxy)phenyl) showed excellent in vivo activities against Candida, Aspergillus and Cryptococcus species. It also showed high tolerance in a preliminary toxicity study in rats.
- Oida, Sadao,Tajima, Yawara,Konosu, Toshiyuki,Nakamura, Yoshie,Somada, Atsushi,Tanaka, Teruo,Habuki, Shinobu,Harasaki, Tamako,Kamai, Yasuki,Fukuoka, Takashi,Ohya, Satoshi,Yasuda, Hiroshi
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p. 694 - 707
(2007/10/03)
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- Heterocyclic compounds having anti-diabetic activity and their use
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Compounds of formula (I): STR1 [wherein: X represents an unsubstituted or substituted indolyl, indolinyl, azaindolyl, azaindolinyl, imidazopyridyl or imidazopyrimidinyl group; Y represents an oxygen or sulfur atom; Z represents a 2,4-dioxothiazolidin-5-ylidenylmethyl, 2,4-dioxothiazolidin-5-ylmethyl, 2,4-dioxooxazolidin-5-ylmethyl, 3,5-dioxooxadiazolidin-2-ylmethyl or N-hydroxyureidomethyl group; R represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a hydroxy group, a nitro group, an aralkyl group or a unsubstituted or substituted amino group; and m is an integer of from 1 to 5] have hypoglycemic and anti-diabetic activities.
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- A short synthesis of 2,3-di(hetero)arylpyrido[3,2-f][1,4]thiazepines
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A reaction sequence leading to the new title compounds is described, the key step of which is the treatment of anions of N-arylmethyl(2-chloropyridyl) methylidene amines with aromatic and heteroaromatic O-ethyl thiocarboxylates.
- Couture, Axel,Deniau, Eric,Grandclaudon, Pierre,Simion, Cristian
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p. 986 - 990
(2007/10/03)
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- Le phenyl-lithium: nouvel agent de metallation du cycle pyridinique
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Nucleophilic addition was the sole reaction of phenyl-lithium with a pyridinic ring; now the novel catalysed metallation, with phenyl-lithium, of many substituted pyridine compounds giving various derivatives in high yields with many different reagents, has been achieved.
- Mallet, Marc
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- Migration du lithium en serie pyridinique: double catalyse et reformage. Acces aux derives de la bromo-2 lithio-3 pyridine et des bromo-4 halogeno-2 lithio-3 pyridines
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The lithium of an organolithium-pyridinic derivative can be moved from one position to an another by an intermolecular reaction.Two new reactions are possible for pyridinic organic synthesis: the isomerisation of any lithio derivative to a more stable one, and a reaction that transforms a mixture of various bromo-lithio derivatives into a single one.The processes involved and the experimental tools used are described in terms of the 2-bromo-3-lithio- and 4-bromo-2-halogeno-3-lithiopyridines derivatives synthesis.
- Mallet, Marc,Branger, Gilles,Marsais, Francis,Queguiner, Guy
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p. 319 - 332
(2007/10/02)
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- Improved Synthesis of 2,3-Disubstituted Pyridines by Metallation of 2-Chloropyridine: a Convenient Route to Fused Polyheterocycles
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Chemoselective directed metallation of 2-chloropyridine allows the synthesis of 2-substituted 3-carbonylated pyridines, advantage being taken of the metallation ortho-directing effect of the halogen, as well as its reactivity towards nucleophiles.Thus (2-chloro-, 2-methoxy-, and 2-amino-3-pyridyl)-ethanones and -arylmethanones as well as carbaldehydes have been prepared.Some of these ortho-disubstituted intermediates have been readily cyclized to fused polyheterocycles such as naphthiridines and aza-analoges of coumarins, xanthones, and acridones.
- Trecourt, Francois,Marsais, Francis,Guengoer, Timur,Queguiner, Guy
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p. 2409 - 2415
(2007/10/02)
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- Atypical Antipsychotic Agents: Patterns of Activity in a Series of 3-Substituted 2-Pyridinyl-1-piperazine Derivatives
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A series of 3-substituted 2-pyridinyl-1-piperazine derivaties have been appended to cyclic imide groups and evaluated for their potential antipsochotic activity.The dopamine receptor affinities of these target molecules, as well as their ability to block apomorphine-induced stereotypy or reverse neuroleptic-induced catalepsy, was dependent on the lipophilic and electronic characteristics of the substituent situated on the pyridine ring.Groups with +? and -? values were most consistent with the desired biological profile of the target molecules, the cyano moiety being the optimum choice.Evaluation of compound 12 in a monkey model of amphetamine psychosis, and the regional selectivity it expresses for the A10 dopaminergic cell bodies in electrophysiological experiments, suggest this compound would be an atypical antipsychotic agent with few side effects.
- New, James S.,Yevich, Joseph P.,Temple, Davis L.,New, Kimberly B.,Gross, Sharon M.,et al.
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p. 618 - 624
(2007/10/02)
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- ANTIPSYCHOTIC CYCLIC IMIDE DERIVATIVES OF 2-(4-BUTYLPIPERAZIN-1-YL) PYRIDINES, COMPOSITIONS AND USE
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Disubstituted N,N-piperazinyl derivatives are disclosed wherein one substituent is a substituted pyridin-2-yl ring and the second substituent is a butylene chain attached to cyclic imide heterocycles such as azaspiro 4.5!decanedione, dialkylglutarimide, thiazolidinedione, spirocyclopentylthiazolidinedione, or morpholine-2,6-dione. The compounds have psychotropic properties and 2-4-4-(2,4-dioxo-1-thia-3-azaspiro 4. 5!nonane-3-yl)butyl!-1-piperazinyl!-pyridine-3-carboxaldehyde is a typical embodiment having selective antipsychotic activity.
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- ANTIPSYCHOTIC CYCLIC IMIDE DERIVATIVES OF 2-(4-BUTYLPIPERAZIN-1-YL)PYRIDINES, COMPOSITIONS AND USE
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Disubstituted N,N-piperazinyl derivatives are disclosed wherein one substituent is a substituted pyridin-2-yl ring and the second substituent is a butylene chain attached to cyclic imide heterocycles such as azaspiro 4.5!decanedione, dialkylglutarimide, thiazolidinedione, spirocyclopentylthiazolidinedione, or morpholine-2,6-dione. The compounds have psychotropic properties and 2-4-4-(2,4-dioxo-1-thia-3-azaspiro 4. 5!nonane-3-yl)butyl!-1-piperazinyl!pyridine-3-carboxaldehyde is a typical embodiment having selective antipsychotic activity.
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