cas 66336-42-3, 8-Methyl-1,4-dioxaspiro[4,5]decan-8-ol

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Assembly of tricyclic compounds that include the spiro[4.4]nonane subunit
Spiroannulation of ketals derived from unsaturated cyclohexenone derivatives by the Lewis acid-catalyzed reaction of l,2-bis((trimethylsilyl)oxy)cyclobutene 5 led to spiro[4.5]decene-diones 9 and 30. These were transformed into spiro[4.4]nonene derivatives 25 and 35/36 via similar sequences involving ozonolysis and aldol ring reclosure. Reduction of an annular double bond allowed facile closure of a third ring, also by an aldol reaction. This work led to a single oxygenated angular triquinane 28 from 9, and to the tricyclo[6.2.1.01,5]undecane derivative 41 from 30. An oxatricyclo[5.3.1.01,5]undecane derivative 19 was also obtained from 9.
Liu,Wu,Burnell
p. 656 - 664
(1997)
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1H-PYRROLO[2,3-B]PYRIDINE DERIVATIVES AS BCL-2 INHIBITORS FOR THE TREATMENT OF NEOPLASTIC AND AUTOIMMUNE DISEASES
The present invention relates to lH-pyrrolo[2,3-b]pyridine derivatives and related compounds as BCL-2 inhibitors for treating neoplastic, autoimmune or neurodegenerative diseases. The present description discloses the synthesis and characterisation of exemplary compounds as well as pharmacological data thereof (e.g. pages 162 to 233; examples 1 to 8; table; compound examples cpd-1 to cpd-135; biological examples 1 to 4).
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Page/Page column 191; 198-199

(2021/07/02)

Synthesis and evaluation of 1,1,7,7-tetramethyl-9-azajulolidine (TMAJ) as a highly active derivative of N,N-dimethylaminopyridine
1,1,7,7-Tetramethyl-9-azajulolidine (TMAJ), which theoretical studies have suggested as a highly active DMAP analog, was synthesized for the first time. The catalytic activity of TMAJ was confirmed by the acetylation reactions of various tert-alcohols. TMAJ showed much higher catalytic activity than DMAP and one of the highest activity levels among the conventional DMAP analogs. These experimental results were in good agreement with the previous theoretical studies.
Tsutsumi, Tomohiro,Saitoh, Arisa,Kasai, Tomoyo,Chu, MengYue,Karanjit, Sangita,Nakayama, Atsushi,Namba, Kosuke
supporting information

(2020/05/28)

Application of Transaminases in a Disperse System for the Bioamination of Hydrophobic Substrates
The challenging bioamination of hydrophobic substrates has been attained through the employment of a disperse system consisting of a combination of a low polarity solvent (e. g. isooctane or methyl-tert-butylether), a non-ionic surfactant and a minimal amount of water. In these conditions, amine transaminases (ATA) were shown to efficiently carry out the reductive amination of variously substituted cyclohexanones, providing good conversions often coupled with a superior stereoselectivity if compared with the corresponding chemical reductive amination. An array of synthetically useful 4-substituted aminocyclohexanes was consequentially synthesized through biocatalysis, analyzed and stereochemically characterized. (Figure presented.).
Berglund, Per,Fiorati, Andrea,Humble, Maria S.,Tessaro, Davide
(2020/02/04)

Design and Optimization Leading to an Orally Active TTK Protein Kinase Inhibitor with Robust Single Agent Efficacy
Triple negative breast cancer (TNBC) is an aggressive disease with high relapse rates and few treatment options. Outlined in previous publications, we identified a series of potent, dual TTK/CLK2 inhibitors with strong efficacy in TNBC xenograft models. P
Riggs, Jennifer R.,Elsner, Jan,Cashion, Dan,Robinson, Dale,Tehrani, Lida,Nagy, Mark,Fultz, Kimberly E.,Krishna Narla, Rama,Peng, Xiaohui,Tran, Tam,Kulkarni, Ashutosh,Bahmanyar, Sogole,Condroski, Kevin,Pagarigan, Barbra,Fenalti, Gustavo,Lebrun, Laurie,Leftheris, Katerina,Zhu, Dan,Boylan, John F.
supporting information
p. 4401 - 4410
(2019/05/17)

Bcl-2 INHIBITORS
Disclosed herein is a compound of Formula (I) for inhibiting Bcl-2 and treating disease associated with undesirable bcl-2 activity (Bcl-2 related diseases), a method of using the compounds disclosed herein for treating dysregulated apoptotic diseases including cancers and treating autoimmune disease, and a pharmaceutical composition comprising the same.
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Paragraph 0626; 0627; 0628

(2019/11/19)

Deoxygenative Borylation of Secondary and Tertiary Alcohols
Two different approaches for the deoxygenative radical borylation of secondary and tertiary alcohols are presented. These transformations either proceed through a metal-free silyl-radical-mediated pathway or utilize visible-light photoredox catalysis. Readily available xanthates or methyl oxalates are used as radical precursors. The reactions show broad substrate scope and high functional-group tolerance, and are conducted under mild and practical conditions.
Friese, Florian W.,Studer, Armido
supporting information
p. 9561 - 9564
(2019/06/21)

The Discovery of a Dual TTK Protein Kinase/CDC2-Like Kinase (CLK2) Inhibitor for the Treatment of Triple Negative Breast Cancer Initiated from a Phenotypic Screen
Triple negative breast cancer (TNBC) remains a serious unmet medical need with discouragingly high relapse rates. We report here the synthesis and structure-activity relationship (SAR) of a novel series of 2,4,5-trisubstituted-7H-pyrrolo[2,3-d]pyrimidines with potent activity against TNBC tumor cell lines. These compounds were discovered from a TNBC phenotypic screen and possess a unique dual inhibition profile targeting TTK (mitotic exit) and CLK2 (mRNA splicing). Design and optimization, driven with a TNBC tumor cell assay, identified potent and selective compounds with favorable in vitro and in vivo activity profiles and good iv PK properties. This cell-based driven SAR produced compounds with strong single agent in vivo efficacy in multiple TNBC xenograft models without significant body weight loss. These data supported the nomination of CC-671 into IND-enabling studies as a single agent TNBC therapy.
Riggs, Jennifer R.,Nagy, Mark,Elsner, Jan,Erdman, Paul,Cashion, Dan,Robinson, Dale,Harris, Roy,Huang, Dehua,Tehrani, Lida,Deyanat-Yazdi, Gordafaried,Narla, Rama Krishna,Peng, Xiaohui,Tran, Tam,Barnes, Leo,Miller, Terra,Katz, Jason,Tang, Yang,Chen, Ming,Moghaddam, Mehran F.,Bahmanyar, Sogole,Pagarigan, Barbra,Delker, Silvia,Lebrun, Laurie,Chamberlain, Philip P.,Calabrese, Andrew,Canan, Stacie S.,Leftheris, Katerina,Zhu, Dan,Boylan, John F.
supporting information
p. 8989 - 9002
(2017/11/14)

COMPOUNDS USEFUL AS KINASE INHIBITORS
This invention relates to novel compounds. The compounds of the invention are tyrosine kinase inhibitors. Specifically, the compounds of the invention are useful as inhibitors of Bruton's tyrosine kinase (BTK).The invention also contemplates the use of the compounds for treating conditions treatable by the inhibition of Bruton's tyrosine kinase, for example cancer, lymphoma, leukemia and immunological diseases.
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Paragraph 00287

(2017/07/14)

Construction of Distant Stereocenters by Enantioselective Desymmetrizing Carbonyl-Ene Reaction
An efficient desymmetrizing carbonyl-ene reaction of 1-substituted 4-methylenecyclohexanes with glyoxal derivatives was thus executed by a chiral N,N′-dioxide/NiII catalyst, providing facile access to cyclohexene derivatives bearing two remote 1,6-related stereocenters. This distal stereocontrol methodology originates from the efficient interaction between the catalyst with enophiles, discrimination of the two chair conformations of olefinic components, and the intrinsic six-membered transition-state structure of ene process.
Luo, Weiwei,Lin, Lili,Zhang, Yu,Liu, Xiaohua,Feng, Xiaoming
supporting information
p. 3374 - 3377
(2017/07/15)

PYRAZOLOPYRIMIDINE DERIVATIVES AS BTK INHIBITORS FOR THE TREATMENT OF CANCER
This invention relates to novel compounds. The compounds of the invention are tyrosine kinase inhibitors. Specifically, the compounds of the invention are useful as inhibitors of Bruton's tyrosine kinase (BTK). The invention also contemplates the use of t
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Paragraph 00516; 00517

(2017/05/02)

Novel indazoles for the treatment and prophylaxis of respiratory syncytial virus infection
The invention provides novel compounds having the general formula: wherein R1, R2, R3, R4, R5, R7, A1, A2 and A3 are as described herein, compositions including the compounds and methods of using the compounds.
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Paragraph 0438-0439

(2016/08/17)

IDO INHIBITORS
There are disclosed compounds that modulate or inhibit the enzymatic activity of indoleamine 2,3-dioxygenase (IDO), pharmaceutical compositions containing said compounds and methods of treating proliferative disorders, such as cancer, viral infections and/or inflammatory disorders utilizing the compounds of the invention.
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Paragraph 0471

(2016/10/27)

Novel indazoles for the treatment and prophylaxis of respiratory syncytial virus infection
The invention provides novel compounds having the general formula: wherein R1, R2, R3, R4, R5, R7, A1, A2 and A3 are as described herein, compositions including the compounds and methods of using the compounds.
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Paragraph 0437; 0438

(2015/06/17)

TRITERPENOIDS WITH HIV MATURATION INHIBITORY ACTIVITY, SUBSTITUTED IN POSITION 3 BY A NON-AROMATIC RING CARRYING A HALOALKYL SUBSTITUENT
Compounds having drug and bio-affecting properties, their pharmaceutical compositions and methods of use are set forth. In particular, triterpenoids that possess unique antiviral activity are provided as HIV maturation inhibitors, as represented by compounds of Formula I: with X selected from C4-8 cycloalkyl, C4-8 cycloalkenyl, C4-9 spirocycloalkyl, C4-9 spirocycloalkenyl, C4-8 oxacycloalkyl, C4-8 dioxacycloalkyl, C6-8 oxacycloalkenyl, C6-8 dioxacycloalkenyl, C6 cyclodialkenyl, C6 oxacyclodialkenyl, C6-9 oxaspirocycloalkyl and C6-9 oxaspirocycloalkenyl ring, such that X is substituted with A, wherein A is -C1-6 alkyl- halo. These compounds are useful for the treatment of HIV and AIDS.
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Page/Page column 234; 235

(2015/11/03)

Synthesis and biological evaluation of picolinamides as potent inhibitors of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1)
Synthesis of a series of 6-substituted picolinamide derivatives and their inhibitory activities against 11β-hydroxysteroid dehydrogenase type 1 are described. Optimization of the initial hit compound, N-cyclohexyl-6-(piperidin-1-yl)picolinamide (1) from high throughput screening of in-house library resulted in the discovery of the highly potent and metabolically stable compound 25, which was efficacious in a mouse ex vivo pharmacodynamic model and reduced the fasting blood glucose and insulin levels in a HF/STZ mouse model after oral dosing.
Ryu, Je Ho,Kim, Shinae,Han, Hye Young,Son, Hyun Joo,Lee, Hyun Jung,Shin, Young Ah,Kim, Jae-Sun,Park, Hyeung-Geun
p. 695 - 700
(2015/01/30)

NOVEL INDAZOLES FOR THE TREATMENT AND PROPHYLAXIS OF RESPIRATORY SYNCYTIAL VIRUS INFECTION
The invention provides novel compounds having the general formula: formula (I) wherein R1, R2, R3, R4, R5, R7, A1, A2 and A3 are as described herein, compositions including the compounds and methods of using the compounds.
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Page/Page column 89

(2014/02/15)

SUBSTITUTED PYRROLOPYRIMIDINE COMPOUNDS, COMPOSITIONS THEREOF, AND METHODS OF TREATMENT THEREWITH
Provided herein are Pyrrolopyrimidine Compounds having the following structure: wherein R1, R2, R3, and L are as defined herein, compositions comprising an effective amount of a Pyrrolopyrimidine Compound, and methods for treating or preventing breast cancer, more particularly triple negative breast cancer, comprising administering an effective amount of such Pyrrolopyrimidine Compounds to a subject in need thereof.
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Paragraph 0294

(2014/07/23)

GERMINAL ALKOXY/ALKYLSPIROCYCLIC SUBSTITUTED TETRAMATE DERIVATIVES
The invention relates to novel compounds of the formula (I) in which W, X, Y, Z, A, B and G have the meanings given above, to a plurality of processes and intermediates for their preparation, and to their use as pesticides and/or herbicides. The invention also provides selective herbicidal compositions comprising, firstly, geminally alkoxy/alkylspirocyclically substituted tetramic acid derivatives and, secondly, a crop plant compatibility-improving compound. The invention furthermore relates to the boosting of the action of crop protection compositions comprising compounds of the formula (I) through the addition of ammonium salts or phosphonium salts and optionally penetrants.
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Paragraph 0599; 0600; 0601; 0602

(2014/08/07)

METABOTROPIC GLUTAMATE RECEPTOR 5 MODULATORS AND METHODS OF USE THEREOF
Compounds that modulate GluR5 activity and methods of using the same are disclosed.
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Page/Page column 107

(2013/02/27)

ETHER DERIVATIVES OF BICYCLIC HETEROARYLS
The invention relates to compounds of formula (I), wherein the substituents are as defined in the specification; to processes for the preparation of such compounds; pharmaceutical compositions comprising such compounds; such compounds as a medicament; such compounds for the treatment of a proliferative disease
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Page/Page column 83

(2011/04/18)

PICOLINAMIDE AND PYRIMIDINE-4-CARBOXAMIDE COMPOUNDS, PROCESS FOR PREPARING AND PHAMACEUTICAL COMPOSITION COMPRISING THE SAME
Provided are picolinamide and pyrimidine-4-carboxamide compounds, a method for preparing the same, a pharmaceutical composition containing the same, and a medical use using the compound as an agent for preventing, regulating, and treating diseases related to regulation of glucocorticoids by using selective inhibitory activity of the compound for an 11β-HSD1 enzyme. The picolinamide and pyrimidine-4-carboxamide compounds of the present invention are selective inhibitors of human-derived 11β-HSD1 enzymes, and are useful in an agent for preventing, regulating, and treating diseases related to glucocorticoid regulation in which human- derived 11β-HSD1 enzymes are involved, for example, metabolic syndromes such as, type 1 and type 2 diabetes, diabetes later complications, latent autoimmune diabetes adult (LAD A), insulin tolerance syndromes, obesity, impaired glucose tolerane (IGT), impaired fasting glucose (IFG), damaged glucose tolerance, dyslipidemia, atherosclerosis, hypertension, etc.
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Page/Page column 90

(2011/11/30)

Geminal alkoxy/alkylspirocyclic substituted tetramate derivatives
The invention relates to novel compounds of the formula (I) in which W, X, Y, Z, A, B and G have the meanings given above, to a plurality of processes and intermediates for their preparation, and to their use as pesticides and/or herbicides. The invention
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Page/Page column 41

(2010/11/03)

DUAL MODULATORS OF 5HT2A AND D3 RECEPTORS
The present invention relates to compounds of the formula (I) wherein R1, R2, X and n are as defined in the specification as dual modulators of the serotonin 5-HT2a and dopamine D3 receptors, their manufacture,
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Page/Page column 44

(2009/02/11)

1- (1-CYCLOHEXYL-4-PIPERIDINYL) -1, 3-DIHYDRO-2H-BENZIMIDAZOL-2-ONE DERIVATIVES WHICH HAVE ACTIVITY ON THE M1 RECEPTOR AND THEIR USE IN MEDICINE
Compounds of Formula (I) or a salt thereof are provided: wherein R1, R2, R4, R5, R6, Q and Z are as defined in the description. Uses of the compounds as medicaments and in the manufacture of medicamen
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Page/Page column 49

(2008/12/04)

New bioorganic reagents: Evolved cyclohexanone monooxygenase - Why is it more selective?
Four mutants of the cyclohexanone monooxygenase (CHMO) evolved as catalysts for Baeyer-Villiger oxidation of 4-hydroxycyclohexanone were investigated as catalysts for a variety of 4-substituted and 4,4-disubstituted cyclohexanones. Several excellent catalytic matches (mutant/substrate) were identified. The most important, however, is the finding that, in a number of cases, a mutant with a single exchange, Phe432Ser, was shown to be as robust and more selective as a catalyst than the wild-type CHMO. All biotransformations were performed on a laboratory scale, allowing full characterization of the products. The absolute configurations of two products were established. A model suggesting a possible role of the 432 serine residue in enantioselectivity control is proposed.
Kayser, Margaret M.,Clouthier, Christopher M.
p. 8424 - 8430
(2007/10/03)

Highly efficient conversion of alcohols to isocyanides
Treatment of tertiary alcohols with silver salts (AgClO4, AgBF4, or AgOTf) and trimethylsilyl cyanide (TMSCN), followed by hydrolysis, directly affords excellent yields of corresponding isocyanides. This reaction proceeds selectively
Kitano,Chiba,Tada
p. 437 - 443
(2007/10/03)

Studies toward the synthesis of menogaril: Synthesis of a-ring precursors and their conversion to the tetracyclic core via the benzannulation reaction
A model study for the synthesis of menogaril is reported which involves the benzannulation reaction of a Fischer carbene complex with an alkyne that contains the A-ring of the tetracyclic core of menogaril. The synthesis of methoxy and benzyloxy derivatives of this alkyne are reported as well as the reaction of the methoxy derivative with an o-methoxyphenyl carbene complex to generate a tricyclic naphthol containing three of the four rings of menogaril core. Completion of the model study and the synthesis of the tetracyclic anthracyclinone core of menogaril was accomplished by an intramolecular Friedel-Crafts cyclization.
Wulff, William D.,Su, Jing,Tang, Peng-Cho,Xu, Yao-Chang
p. 415 - 422
(2007/10/03)

Dependence of intramolecular dissociative electron transfer rates on driving force in Donor-Spacer-Acceptor systems
The voltammetric reduction of a series of phenyl-substituted 4- benzoyloxy-1-methylcyclohexyl bromides has been investigated in DMF. The reduction leads to the cleavage of the C-Br bond. On a thermodynamic ground, the direct reduction of the tertiary C-Br function is easier than that of the selected benzoates by at least 0.5 V. However, since the direct reduction of bromides is affected by a large activation overpotential, the electron is first located in the benzoate moiety. The rate constant for the following exergonic intramolecular dissociative electron transfer was determined by kinetic analysis of the cyclic voltammetry curves. The intermolecular rate constants for the reaction between the radical anions of methyl benzoates and 4-tert-butyl-1-methylcyclohexyl bromide were also determined and found to correlate very well with related literature data pertaining to tert-butyl bromide. The intramolecular rate constants were found to be more sensitive to variation of driving force than the corresponding intermolecular data. This result can be attributed to a shift of the center of the π* orbital of the radical anion donor away from the acceptor moiety, the shift being larger for the most easily reduced donors. The resulting distance increase is therefore envisaged as responsible for a more rapid rate drop, compared to the intermolecular pattern, when smaller driving forces are considered.
Antonello, Sabrina,Maran, Flavio
p. 5713 - 5722
(2007/10/03)

On the regioselectivity of the Baeyer-Villiger reaction of 2,6-dialkyl cyclohexanones: Application to the synthesis of sordidin, a male pheromone emitted by Cosmopolites sordidus
The diastereoselective synthesis of (1S*,3R*,5R*,7S*)-2,8-dioxa-1-ethyl-3,5,7-trimethylbicyclo[3.2.1]o ctane (1d) has been achieved using as the key step the regioselective Baeyer-Villiger reaction of 2,6-disubstituted cyclohexanone.
Beauhaire, Josiane,Ducrot, Paul-Henri
p. 413 - 418
(2007/10/03)

Identification and Synthesis of Sordidin, a Male Pheromone Emitted by Cosmopolites sordidus.
The diastereoselective synthesis of (1S*,3R*,5R*,7S*) 2,8-dioxa 1-ethyl 3,5,7-trimethyl bicyclooctane 1d has been achieved using as key-step the regioselective Baeyer-Villiger reaction of 2,6-disubstitute
Beauhaire, Josiane,Ducrot, Paul-Henri,Malosse, Christian,Rochat, Didier,Ndiege, Isaiah O.,Otieno, Dalmas O.
p. 1043 - 1046
(2007/10/02)