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Amino 6-membered ring derivative and pharmaceutical applications thereof including the use for manufacturing dipeptidyl peptidase-4(IDPP-IV) inhibitor
The present invention relates to an amino 6-membered ring derivative and pharmaceutical applications thereof, which specifically relates to the amino 6-membered ring derivative represented by the general formula (I) or stereoisomers thereof, pharmaceutically acceptable salts thereof, a prodrug, a pharmaceutical composition comprising the derivative, and the pharmaceutical use for manufacturing dipeptidyl peptidase-4(IDPP-IV) inhibitor, wherein the definition of each substituent in the general formula (I) is the same as described in the specification.
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Page/Page column 38

(2017/07/31)

Asymmetric reduction of ketones catalyzed by α,α-diphenyl-(L)-prolinol modified with imidazolium ionic liquid and BH3·SMe2 as a recoverable catalyst
The synthesis of α,α-diphenyl-4-trans-hydroxy-(L)-prolinol modified with imidazolium based ionic liquids was carried out with trans-α,α-diphenyl-4-hydroxy-(L)-prolinol, 5-bromovaleric acid or 1,5-dibromopentane and imidazole. α,α-Diphenyl-4-hydroxy-(L)-prolinol modified with imidazolium ionic liquid was treated with BH3·SMe2 which generate 1,3,2-oxazaborolidine, that acts as a catalyst for asymmetric reduction of prochiral ketones. α,α-Diphenyl-4-hydroxy-(L)-prolinol modified with imidazolium ionic liquids (PF6 anion) with BH3?SMe2 found to be an efficient catalyst (10 mol%) for the reduction of the acetophenone, gave 99% yield and 87-84% ee. The catalytic method has wide applicability for a variety of substrates. 1,3,2-oxazaborolidine containing ether linkage ionic liquid was recovered and reused up to 4 cycles with 99-91% yields and 87-81% ee's.
Chauhan, ManMohan Singh,Singh, Surendra
p. 184 - 189
(2015/02/19)

A formal synthesis of (+)-lactacystin from 4-hydroxyproline
A formal synthesis of (+)-lactacystin has been completed from trans-4-hydroxyproline, using a diastereoselective enolate acylation reaction as a key step. Diastereoselectivity was seen to vary as a function of the steric bulk of the C4-O-protecting group, and contrary to expectations, the best diastereoselectivities were obtained when the small methyl carbonate protecting group was used. The formal synthesis was then completed by intercepting Shibasaki's route via methyl carbonate deprotection, dehydration, 3-pyrroline to 3-pyrrolinone oxidation, hydrogenation and N-CO2Me deprotection.
Mycock, David K.,Glossop, Paul A.,Lewis, William,Hayes, Christopher J.
supporting information
p. 55 - 57
(2013/02/21)

A heterogeneous layered bifunctional catalyst for the integration of aerobic oxidation and asymmetric C-C bond formation
The design and synthesis of a heterogeneous bifunctional chiral catalyst for the sequential aerobic oxidation-asymmetric Michael reactions between primary allylic alcohols and dibenzyl malonate are described. Interestingly, we found that layering bimetallic nanoparticles over the organocatalyst, within the chiral composite material, is crucial for catalytic activity.
Miyamura, Hiroyuki,Choo, Gerald C. Y.,Yasukawa, Tomohiro,Yoo, Woo-Jin,Kobayashi, Shu
supporting information
p. 9917 - 9919
(2013/10/22)

HETEROCYCLIC COMPOUNDS AND METHODS FOR THEIR USE
The present invention relates to heterocyclic compounds useful for antagonising angiotensin II Type 2 (AT2) receptor. More particularly the invention relates to pyrrolidine and azetidine compounds, compositions containing them and their use in methods of treating or preventing disorders or diseases associated with AT2 receptor function including neuropathic pain, inflammatory pain, conditions associated with neuronal hypersensitivity, impaired nerve conduction velocity, cell proliferation disorders, disorders associated with an imbalance between bone resorption and bone formation and disorders associated with aberrant nerve regeneration.
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Page/Page column 159; 160

(2013/07/19)

HYDROGEN CHLORIDE SALT OF A SUBSTITUTED 5-OXAZOL-2-YL-QUINOLINE COMPOUND AND A PROCESS FOR THE PRODUCTION THEREOF
The present invention relates to the compound of the Formula I: and to methods of treating upper and lower obstructive airway diseases using said compound, to formulations comprising it, and to a particular crystalline form and processes of synthesis of the crystalline form. IM=105109
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Page/Page column 4

(2011/01/12)

Design and stereoselective synthesis of four peptide nucleic acid monomers with cyclic structures in backbone
Four isomers of the monomer of peptide nucleic acid (PNA) were derived from (2S,4R)-4-hydroxyproline; they had different stereochemistries at the C 2 and C4 positions in the pyrrolidine ring. These different backbone conformations corresponding to four different stereochemistries were realized through a combination of inversions at the C2 and the C4 positions in pyrrolidine ring. The obtained backbone frameworks were reacted with N-benzoyl thymine to give the corresponding PNA monomers. Spectroscopic comparison of the resultant monomers confirmed their stereochemistries.
Watanabe, Akiko,Kiyota, Naotoshi,Yamasaki, Tetsuo,Tanda, Kazuhiro,Miyagoe, Tatsunori,Sakamoto, Masanori,Otsuka, Masami
experimental part
p. 1132 - 1139
(2011/11/05)

Heck reaction on morita-baylis-hillman adducts: Diastereoselective synthesis of pyrrolizidinones and pyrrolizidines
An efficient approach to the diastereoselective synthesis of benzylidene-, benzyl-pyrrolizidinones, and pyrrolizidines is described. The sequence is based on a highly stereoselective Heck reaction between a hydroxylated pyrrolizidinone, prepared from a Morita-Baylis-Hillman adduct, and a suitable aryl halide, using Nájeras oxime derived palladacycle as catalyst. Georg Thieme Verlag Stuttgart - New York.
Delunafreire, Kristerson R.,Tormena, Cláudio F.,Coelho, Fernando
supporting information; experimental part
p. 2059 - 2063
(2011/10/09)

A general approach for preparation of polymer-supported chiral organocatalysts via acrylic copolymerization
(Figure Presented) Polymer-supported chiral organocatalysts, as well as most other forms of immobilized catalysts, are traditionally prepared by a postmodification approach where modified catalyst precursors are anchored onto prefabricated polymer beads. Herein, we report an alternative and more scalable approach where polymer-supported chiral enamine and iminium organocatalysts are prepared in a bottom-up fashion where methacrylic functional monomers are prepared in an entirely nonchromatographic manner and subsequently copolymerized with suitable comonomers to give cross-linked polymer beads. All syntheses have been conducted on multigram scale for all intermediates and finished polymer products, and the catalysts have proven successful in reactions taking place in solvents spanning a wide range of solvent polarity. While polymer-supported proline and prolineamides generally demonstrated excellent results and recycling robustness in asymmetric aldol reactions of ketones and benzaldehydes, the simplest type of Joargensen/Hayashi diarylprolinol TMS-ether showed excellent selectivity, but rather sluggish reactivity in the Enders-type asymmetric cascade. The polymer-supported version of the first-generation MacMillan imidazoHdinone had a pattern of reactivity very similar to that of the monomeric catalyst, but is too unstable to allow recycling.
Kristensen, Tor E.,Vestli, Kristian,Jakobsen, Martin G.,Hansen, Finn K.,Hansen, Tore
supporting information; experimental part
p. 1620 - 1629
(2010/04/29)

Total synthesis of (+)-dibromophakellin
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Imaoka, Takuya,Iwamoto, Osamu,Noguchi, Kei-Ichi,Nagasawa, Kazuo
supporting information; experimental part
p. 3799 - 3801
(2009/09/24)

XINAFOATE SALT OF A SUBSTITUTED 5-OXAZOL-2-YL-QUINOLINE COMPOUND
The present invention relates to the compound of the formula (I). To methods of treating upper and lower obstructive airway diseases using said compound, to formulations comprising it, and to polymorphs and processes of synthesis of the polymorphic forms.
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Page/Page column 15-16

(2008/06/13)

Concise, stereoselective route to the four diastereoisomers of 4-methylproline
The full stereochemical characterization of 4-methylproline, a rare amino acid found in a number of peptidic secondary metabolites, has often been hindered by long reaction sequences or low stereoselectivity in the synthesis leading to reference samples. The preparation of the four diastereoisomers of 4-methylproline by a concise and stereoselective route is presented and features a six-step route with late-stage stereodivergence, good stereoselectivity for both cis- and trans-series (75% and 88% de, respectively), and good overall yields (cumulative yields of 30-40%). Additional data on the Marfey's derivatives of the stereoisomers are also presented.
Murphy, Annabel C.,Mitova, Maya I.,Blunt, John W.,Munro, Murray H.G.
experimental part
p. 806 - 809
(2009/04/07)

Asymmetric synthesis of 3-amino-4-hydroxy-2-(hydroxymethyl)pyrrolidines as potential glycosidase inhibitors
Three diastereoisomers of 3-amino-4-hydroxy-2-(hydroxymethyl)pyrrolidine have been synthesised by a divergent route starting from trans-4-hydroxy-l- proline. Regio- and stereoselective introduction of the 3-amino and 4-hydroxyl functional groups was achieved using either a tethered aminohydroxylation reaction or by employing intra- and intermolecular epoxide-opening strategies. Preliminary biological data indicate that two of these novel amino pyrrolidines are moderate inhibitors of β-galactosidase. The Royal Society of Chemistry.
Curtis, Kim L.,Evinson, Emma L.,Handa, Sandeep,Singh, Kuldip
p. 3544 - 3553
(2008/09/20)

SUBSTITUTED DIAZABICYCLOHEPTANES AND THEIR USE AS PROTEIN KINASE INHIBITORS
The present invention relates to therapeutic diazobicyclo pyridines and their use in the treatment of arthritis, rheumatoid arthritis, psoriatic arthritis or osteoarthritis, organ transplant, acute transplant or heterograft and homograft rejection, ischemic and reperfusion injury, transplantation tolerance induction, multiple sclerosis, inflammatory bowel disease, ulcerative colitis, Crohn's disease, lupus, graft vs. host diseases, T -cell mediated hypersensitivity diseases, contact hypersensitivity, delayed-type hypersensitivity, gluten-sensitive enteropathy, Type 1 diabetes, psoriasis, contact dermatitis, Hashimoto's thyroiditis, Sjogren's syndrome, autoimmune hyperthyroidism,Graves' Disease, Addison's disease, autoimmune polyglandular disease, autoimmune alopecia, pernicious anemia, vitiligo, autoimmune hypopituatarism, Guillain-Barre syndrome, autoimmune diseases, glomerulonephritis, serum sickness, uticaria, respiratory allergies, asthma, hayfever, allergic rhinitis, skin allergies, scleracielma, mycosis fungoides, acute inflammatory responses, acute respiratory distress syndrome, dermatomyositis, alopecia areata, chronic actinic dermatitis, eczema, Behcet's disease, Pustulosis palmoplanteris, Pyoderma gangrenum, Sezary's syndrome, atopic dermatitis, systemic schlerosis, morphea, Type II diabetes and cancers where PKC theta or other PKC-family kinases are activated, overexpressed or facilitate tumor growth or survival of tumor cells, T cell leukemia, thymoma, T and B cell lymphoma, colon carcinoma, breast carcinoma and lung carcinoma or provides resistance to chemotherapeutic drugs.
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Page/Page column 58-59

(2008/06/13)

Ex-chiral pool synthesis and receptor binding studies of 4-substituted prolinol derivatives
Starting from natural 4-hydroxyproline, preparation of the four possible stereoisomers of 4-amino- and 4-aminomethyl-substituted prolinol derivatives, respectively, was accomplished by chemo- and regioselective functional group transformations at the 2- and 4-positions of the pyrrolidine moiety. These building blocks were used as valuable precursors for the preparation of new methoxybenzamide derivatives. Dopamine and serotonin binding studies involving the subtypes D1, D2long, D2short, D3 and D4 as well as 5-HT1A and 5-HT2, respectively, displayed interesting structure activity relationships, especially with respect to the absolute and relative configuration of the test compounds. As a complement to the D3 receptor preferring aminomethylpyrrolidine FAUC 21, the (2R,4R)-aminoprolinol derivative ent-24 (FAUC 65) preferentially recognizing the D4 subtype was developed.
Heindl, Cornelia,Huebner, Harald,Gmeiner, Peter
p. 3141 - 3152
(2007/10/03)

Benzyl compounds which inhibit leukocyte adhesion mediated by VLA-4
Disclosed are compounds which bind VLA-4. Certain of these compounds also inhibit leukocyte adhesion and, in particular, leukocyte adhesion mediated by VLA-4. Such compounds are useful in the treatment of inflammatory diseases in a mammalian patient, e.g., human, wherein the disease may be, for example, asthma, Alzheimer's disease, atherosclerosis, AIDS dementia, diabetes, inflammatory bowel disease, rheumatoid arthritis, tissue transplantation, tumor metastasis and myocardial ischemia. The compounds can also be administered for the treatment of inflammatory brain diseases such as multiple sclerosis.
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Page column 63

(2010/01/31)

[2-(O-Phenylalkyl)phenoxy]alkylamines III: Synthesis and selective serotonin-2 receptor binding (2).
A series of 12-(2-phenylethyl)phenoxy]ethylpyrrolidine derivatives were synthesized, and their affinity for serotonin-2 (5-HT2) and dopamine-2 (D2) receptors was examined. Among them, compound 17, (2R,4R)-4-hydroxy-2-[2-[2-[2-(3-methoxyphenyl)ethyl]phenoxylethyl] -1-methylpyrrolidine hydrochloride, showed high 5-HT2 receptor affinity in vitro. This compound was a more potent inhibitor of ex vivo 5-HT-induced platelet aggregation than compound 3, which was previously shown to be more potent than ketanserin (1) and sarpogrelate (2a). However, compound 17 produced gastric irritation in rats. Therefore, we carried out a further derivatization of 17, and compound 45 (R-102444), a lauryl ester prodrug of compound 17, was found to be a promising candidate as an antithrombotic agent. Oral administration of R-102444 produced a marked inhibition of 5-HT-induced ex vivo platelet aggregation, and R-102444 did not cause any gastric irritation. The antiaggregatory effects of R-102444 were more potent than those of sarpogrelate (2a) and its active metabolite, M-1 (2b). In addition, R-102444 exhibited more potent antithrombotic effects than sarpogrelate in a rat photochemically-induced thrombosis model.
Tanaka,Goto,Ito,Hayakawa,Sugidachi,Ogawa,Asai,Fujimoto
p. 1729 - 1739
(2007/10/03)

Synthesis and pharmacological activity of 4-amino-5-chloro-2-methoxy-N- [(2S,4S)-1-ethyl-2-hydroxymethyl-4-pyrrolidinyl]benzamide (TKS159) and its optical isomers
Of 4-amino-5-chloro-2-methoxy-N-(1-ethyl-2-hydroxymethyl-4- pyrrolidinyl)benzamide, four optical isomers, (2S,4S)-1 (TKS159), (2S,4R)-25, (2R,4S)-26 and (2R,4R)-27, were prepared from optically active 4-amino-1- ethyl-2-hydroxymethylpyrrolidine di-p-toluenesulfonate [(2S,4S)-14, (2S,4R)- 17, (2R,4S)-20 and (2R,4R)-23, respectively]. The requisites, (2S,4S)-14, (2S,4R)-17, (2R,4S)-20 and (2R,4R)-23, were prepared from a commercially available trans-4-hydroxy-L-proline. The absolute configurations of (2S,4S)-1 (TKS159), (2S,4R)-25, (2R,4S)-26 and (2R,4R)-27 were spectroscopically determined. Of the benzamide derivatives, four optical isomers, (2S,4S)-1, (2S,4R)-25, (2R,4S)-26 and (2R,4R)-27, showed a relatively potent affinity for 5-hydroxytryptamine 4 (5-HT4) receptors in a radioligand binding assay ([3H]GR113808). The activities of 25 - 27 were less effective than that of 1 for the gastric emptying of a phenol red semisolid meal in rats. All this suggests that the most potent of the isomers was 4-amino-5-chloro-2-methoxy- N-[(2S,4S)-1-ethyl-2-hydroxymethyl-4-pyrrolidinyl]benzamide (1).
Yanagi, Toshiharu,Kitajima, Akihiko,Anzai, Kinsei,Kodama, Kazuya,Mizoguchi, Jun-Ichi,Fujiwara, Hiromichi,Sakiyama, Hideyo,Kamoda, Osamu,Kamei, Chiaki
p. 1650 - 1654
(2007/10/03)

Asymmetric syntheses of all four isomers of 4-amino-4-carboxyproline: Novel conformationally restricted glutamic acid analogues
Asymmetric syntheses of all four isomers of 4-amino-4-carboxyprolines, i.e. (2S,4S)-3, (2S,4R)-4, and their corresponding enantiomers, as novel conformationally restricted analogues of glutamic acid, were performed from trans-4-hydroxy-L-proline as a homochiral starting material. The key step was the spirohydantoin ring formation by employing the Bucherer-Bergs reaction of 4-oxoproline derivatives. These structures were determined by NMR studies.
Tanaka,Sawanishi
p. 1641 - 1656
(2007/10/02)

Benzamide derivatives
A benzamide derivative represented by the formula: STR1 having a promoting activity of gastrointestinal tract and pharmacentical composition containing the same.
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(2008/06/13)

New fluorine-substituted analogue of eticlopride with high affinity toward dopamine D2 receptors
Aiming at the development of positron-emitting ligands with specific and high affinity toward dopamine D2 receptors in the central nervous system, we synthesized a new fluorinated eticlopride derivative. A fluorine atom was introduced at the C-4 position of the pyrrolidine ring of eticlopride, a dopamine D2 antagonist of the benzamide series. The in vitro binding affinity of this ligand toward the D2 receptor was found to be as potent as eticlopride, suggesting that the corresponding 18F-labelled compound may be useful as an in vivo radioligand for positron emission tomography.
Watanabe,Fukumura,Sasaki,Maeda,Takehara
p. 3211 - 3214
(2007/10/02)

Transition-Metal-Catalyzed Asymmetric Organic Synthesis via Polymer-Attached Optically Active Phosphine Ligands. 5. Preparation of Amino Acids in High Optical Yield via Catalytic Hydrogenation
Two new optically active phosphinopyrrolidine monomers were prepared by the reaction of (2S,4S)-4-(diphenylphosphino)-2-pyrrolidine and (2R,4R)-4-(diphenylphosphino)-2-pyrrolidine with acryloyl chloride to give N-acryloyl-(2S,4S)-4-(diphenylphosphino)-2-pyrrolidine (1) and N-acryloyl-(2R,4R)-4-(diphenylphosphino)-2-pyrrolidine (2).Copolymerization of 1 and 2 with hydrophilic comonomers and a divinyl monomer provided cross-linked insoluble polymers containing 3-5percentof 1 or 2 that would swell in polar solvents.Exchange of rhodium (I) onto the polymer gave catalysts which were active for the asymmetric hydrogenation of N-acyl α-amino acids in high optical yields, the phosphine derived from the enantiomer of the naturally occurring 4-hydroxyproline giving (S)-amino acids.The catalysts could be reused with no loss in selectivity by simple filtration.
Baker, Gregory L.,Fritschel, Scott J.,Stille, John R.,Stille, John K.
p. 2954 - 2960
(2007/10/02)